How to Ask Someone Out (Without Making It Weird)

Asking someone out successfully requires one clear sentence with a specific activity, time, and place. Skip elaborate justifications and perfect timing. Make a simple, direct invitation that’s easy to accept or decline, then handle their response like a confident adult who respects their decision.

Someone close to me spent three months “building up courage” to ask out a coworker.

Three months of rehearsing the perfect speech. Three months of waiting for the ideal moment. Three months of overthinking every interaction.

When he finally asked, he delivered this rambling monologue about how much he respected her professionally and how he’d been thinking that maybe if she was interested they could potentially explore the possibility of perhaps getting coffee sometime if that wouldn’t be too weird.

She said yes, but later told him she almost said no because the ask was so confusing she couldn’t figure out what he was actually suggesting.

So what I learned from watching him (and hundreds of my clients) struggle with this: asking someone out is just clear communication with a specific ask.

That’s it.

You’re making an offer. They accept or decline. Everyone moves on with their lives.

The weird part comes from everything we pile on top of that simple exchange. The overthinking, the perfect timing, the elaborate justifications, the hedge words that make your request impossible to understand.

So let’s strip it back to what actually works.

How to Ask a Girl Out: The Five Minute Favor Principle

I teach my clients something called the five minute favor in networking contexts. It’s about making requests that are specific, time-bounded, and easy to fulfill.

The same principle applies to asking someone out.

You want to make an offer that’s:

• Specific (what, when, where)
• Low pressure (easy to say no)
• Clear (no confusion about what you’re suggesting)

Bad ask: “Want to hang out sometime?”

Good ask: “I’m checking out that new coffee place on Saturday morning. Want to come with me?”

The difference is specificity. She knows exactly what you’re suggesting, when it would happen, and how much time it involves. She can make a clear decision instead of trying to decode what you mean.

The Psychology of Why We Make This Weird

Most people who struggle with asking others out have the same underlying fear. They think rejection means something bigger than it actually means.

One of my clients put it perfectly: “I was acting like her saying no meant I was fundamentally flawed as a human being.”

But rejection usually means one of these things:

• They’re seeing someone
• They’re not dating anyone right now
• They don’t feel a romantic connection
• The timing doesn’t work
• They prefer to keep work relationships professional

None of those things are about your worth as a person. They’re just facts about the current situation.

What I tell my coaching clients: you’re offering someone the opportunity to spend time with you. If they want that opportunity, great. If they don’t, also great. You’ve got your answer and can move forward accordingly.

The goal is getting clarity, period.

Real Dialogue: Good Asks vs. Bad Asks

Let me show you exactly what these conversations look like. I’ve seen enough people mess this up (and eventually get it right) to know which approaches work.

The Bad Ask #1: The Rambling Justification

“So I was thinking, and I hope this isn’t weird, but I really enjoy talking with you, and I feel like we have a good connection, you know? And I was wondering if maybe you’d be interested in getting coffee or something? I mean, only if you want to. No pressure or anything. I just thought it might be nice to talk somewhere that isn’t work.”

What’s wrong: Way too much explanation. Sounds like you’re trying to convince her instead of simply offering. The “only if you want to” and “no pressure” actually create more pressure because now she has to manage your feelings about her answer.

The Bad Ask #2: The Vague Suggestion

“We should hang out sometime.”

What’s wrong: There’s no specific proposal. “Sometime” could mean anything. She’d have to do the work of figuring out what you actually want and when you want it.

The Bad Ask #3: The Fake Emergency

“My friend cancelled on me last minute for this concert Saturday. You like music, right? Want to come instead?”

What’s wrong: You’re lying about why you’re asking. If she finds out your friend didn’t actually cancel, you look dishonest and manipulative.

The Good Ask #1: Simple and Specific

“I’m going to check out that farmers market Saturday morning. Want to join me?”

Why it works: Clear activity, specific time, easy to visualize. You’re inviting her into something you were already planning to do. Low pressure because you’re not changing your whole day around her answer.

The Good Ask #2: Shared Interest

“You mentioned you love Thai food. There’s this place I’ve been wanting to try downtown. Want to check it out together this weekend?”

Why it works: You’re building on something she already told you she enjoys. Shows you listen. Specific cuisine and timeframe. The “together” makes it clear this is a date invitation.

The Good Ask #3: Activity-Based

“I’m terrible at mini golf but I keep meaning to try that new place. Want to be terrible at it with me Friday after work?”

Why it works: Self-deprecating humor removes performance pressure. Specific activity and timing. The invitation feels collaborative instead of formal.

Asking Someone on a Date: Perfect Timing

What I’ve found working with clients: the best time to ask someone out is when you’re already having a good conversation.

You don’t need to wait for the perfect romantic moment. You don’t need to build up to it over weeks. You just need a conversation where you’re both engaged and enjoying talking to each other.

“This has been really fun talking with you. I’d love to continue this over coffee this weekend.”

You’re extending the current positive interaction, which feels natural instead of random.

Don’t Wait for Perfect Conditions

I think oftentimes people wait for some ideal scenario that never actually happens. The perfect moment when you’re both alone, the conversation naturally leads to dating, and she’s clearly indicating interest.

That moment rarely arrives. Most good relationships start from someone making a simple, direct ask during a perfectly ordinary conversation.

The Two-Week Rule

If you’re interested in asking someone out, do it within two weeks of realizing you’re interested. After that, you start building up the stakes in your head. You start overthinking. You start creating elaborate fantasies about how the ask needs to go.

Two weeks gives you enough time to have a few real conversations and get a sense of whether there’s mutual interest. But it’s not enough time to build the ask up into this huge, terrifying event.

Handling Different Responses

Let’s talk through what actually happens after you ask, because this is where most people’s anxiety lives.

When She Says Yes

“That sounds great. What time works for you?”

Keep it simple. Lock in the logistics. Express enthusiasm but don’t go overboard.

“Perfect. I’ll text you the address. Looking forward to it.”

Done. You’ve got a date. Everything after this is just normal human interaction.

When She Says Maybe

“I might be able to do Saturday. Can I let you know tomorrow?”

This is usually a soft no, but give her the benefit of the doubt and the space she’s asking for.

“Of course. Just text me when you know.”

Then back off. Don’t check in the next day. Don’t try to convince her. If she wants to go, she’ll let you know.

When She Says No

“Thanks for asking, but I can’t this weekend.”

Where most people either get weird or miss obvious cues.

If she offers an alternative (“but I’m free next week”), she’s interested but actually busy.

If she just says no without suggesting another time, she’s declining the date itself, probably for good.

Your response in both cases: “No worries at all. Thanks for being direct.”

That’s it. No asking why. No trying to convince her. No making her explain her reasoning. Just graceful acceptance and moving on.

When She Says No and Gives You Reasons

“I don’t really date people from work” or “I’m not really dating anyone right now.”

Take these at face value. Don’t try to overcome objections like this is a sales call.

“Totally understand. Thanks for being honest.”

The more gracefully you handle rejection, the more likely people are to be direct with you in the future. And the less weird everyone feels afterward.

The Fear Factor: Why This Feels Bigger Than It Is

Most of my clients who struggle with asking people out aren’t actually afraid of rejection. They’re afraid of the aftermath of rejection.

“What if it makes things weird at work?” “What if she tells other people?” “What if I can’t act normal around her anymore?”

What I’ve observed: awkwardness after rejection usually comes from the person who did the asking, not the person who got asked.

If you ask someone out respectfully, they decline respectfully, and you handle it like a normal adult, nothing has to be weird. You had a conversation. You made an offer. They declined. You both move on.

The weirdness comes from:

• Continuing to bring it up
• Acting hurt or angry about the rejection
• Changing how you treat them because they said no
• Making them feel guilty for declining

Avoid those behaviors and there’s no reason for things to be awkward.

The Confidence Paradox

One client told me something that captures this perfectly: “I thought I needed to be confident to ask her out. But it turns out asking her out is what made me confident.”

The confidence doesn’t come first. The action comes first. The confidence follows.

You don’t wait until you feel ready to ask someone out. You ask them out and then feel ready because you took action.

This is backwards from how most people think about it, but it’s how confidence actually works in real life.

Scripts That Actually Work

These aren’t perfect lines to memorize. They’re frameworks you can adapt to your situation and personality.

For Someone You See Regularly (Work, School, Gym)

“I’ve really enjoyed our conversations. Want to continue this over coffee sometime this week?”

Simple, direct, references the existing connection, suggests a specific timeframe.

For Someone You’ve Just Met

“This has been fun talking with you. I’d love to take you to dinner if you’re interested.”

Acknowledges the current positive interaction, makes a clear invitation.

For Someone You Know Through Friends

“I’d love to take you out sometime. Are you free for lunch this weekend?”

Simple, specific timeframe, casual activity that’s not a huge time commitment.

For Online Dating

“Your profile mentions you love hiking. I know a great trail about 20 minutes from downtown. Want to check it out together this Saturday?”

References something specific from their profile, suggests concrete activity and timing.

The Follow-Up Text

If they said yes in person but you need to coordinate details:

“Looking forward to Saturday. I’ll pick you up at 10, or would you rather meet there?”

Confirms enthusiasm, handles logistics, gives them control over the pickup situation.

What to Do When You’re Nervous

Everyone gets nervous asking people out. The people who are good at it aren’t less nervous. They just don’t let the nervousness stop them from doing it.

Some strategies that work:

Practice with Lower Stakes

Ask out people you’re mildly interested in before asking out the person you’re really excited about. Not to use them for practice, but to get comfortable with the mechanics of making the ask.

The conversation flow is the same whether you’re asking out your dream person or someone you’re just curious about.

Focus on the Clarity, Not the Outcome

Your goal is to find out if they’re interested. Whether they say yes or no, you’ve accomplished that goal.

Frame it as information gathering instead of trying to convince them to say yes.

Remember It’s a Normal Human Interaction

You’re not proposing marriage. You’re not asking them to relocate to another country. You’re suggesting you spend 2-3 hours together doing something fun.

Keep the stakes appropriately sized in your head.

Have Something Else Going On

The people who are best at asking others out are also the people with full lives who don’t need any particular person to say yes.

When you’ve got other things you’re excited about, other people you enjoy spending time with, other activities that bring you joy, asking someone out stops feeling like such a big deal.

Common Mistakes That Make It Weird

Asking Via Text When You See Them In Person

If you talk to this person regularly in real life, ask them in real life. Asking via text when you could ask face-to-face makes it seem like you’re afraid of their reaction.

The only time to ask via text is when you genuinely don’t see them in person regularly.

Over-Planning the Perfect Moment

There’s no perfect moment. There are just moments when you’re both in a good mood and having a decent conversation.

Stop waiting for the stars to align and just ask during any reasonably positive interaction.

Making It About Your Feelings

“I really like you” or “I have feelings for you” puts pressure on them to respond to your emotional state before they’ve even had a chance to think about whether they want to go out with you.

Lead with the invitation, not with your feelings about them.

Asking Multiple Times After Getting No

If someone says no, that’s your answer. Asking again a few weeks later because “maybe things have changed” makes you look like you don’t listen or respect boundaries.

There are exceptions (like if they said they weren’t dating anyone but you know they’re single again), but generally: one ask per person.

Making it Too Big

Don’t ask someone out for a weekend trip or a fancy dinner or concert tickets that cost $200. Start small. Coffee, lunch, a simple activity.

Save the elaborate dates for when you’re actually dating, not just trying to figure out if you want to date.

After You Ask: What Changes and What Doesn’t

Regardless of their answer, what should stay the same:

How you treat them day to day. How you interact in group settings. How you respond when they need something work-related. Your general demeanor around them.

If they said yes, you can add some light flirting and date planning to the mix. But the fundamental relationship dynamic shouldn’t dramatically shift overnight.

If they said no, you continue being the same person you were before you asked. Friendly, professional, normal.

The ask was one conversation. It doesn’t have to define every future conversation.

When to Move On

You’ve asked. They’ve answered. Now what?

If they said yes: plan the date, follow through, see how it goes.

If they said no: accept it gracefully and focus your romantic attention elsewhere.

If they said maybe and then never followed up: treat it as a no and move on.

The mistake I see people make is continuing to invest emotional energy in someone who’s already given them clarity. Take the information they’ve given you and make decisions based on that information.

Building the Skill

Like any social skill, asking people out gets easier with practice. The first few times feel huge and scary. After a while, it becomes just another conversation you know how to have.

Start with people you’re mildly interested in. Work your way up to higher-stakes situations. Get comfortable with both outcomes.

Remember that every person who’s good at dating has been rejected many times. Rejection is part of the process, which means it happens to everyone.

The people who end up in great relationships aren’t the ones who never get rejected. They’re the ones who ask enough people out that they eventually find the person who’s excited to say yes.

Your job is to be someone worth saying yes to, then make it easy for the right person to do that.

Your Next Move

Think about someone you’d like to ask out. Pick a specific activity and timeframe. Practice the actual words you’ll use.

Then just ask.

The conversation you’re imagining is probably more complicated than the conversation that will actually happen. Most people appreciate directness and clarity.

So give them both.

Ready to master the social skills that make asking people out feel natural? Discover your social confidence level and get a personalized plan to build real connection skills that work in dating and beyond.

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Frequently Asked Questions

How do you ask someone out without being awkward?

Be specific, direct, and low-pressure. Suggest a concrete activity with a specific timeframe. Avoid rambling explanations or hedge words. Example: “I’m checking out that new coffee place Saturday morning. Want to join me?” Keep it simple and treat it like any other invitation.

When is the right time to ask someone out?

Ask within two weeks of realizing you’re interested, during a conversation where you’re both engaged and enjoying talking. Don’t wait for the “perfect moment”, any positive interaction where you’re both in good moods works. The key is natural conversation flow, not romantic timing.

How do you handle rejection when asking someone out?

Accept it gracefully with “No worries at all. Thanks for being direct.” Don’t ask why, try to convince them, or make them explain their reasoning. Handle rejection respectfully to avoid awkwardness and preserve whatever relationship you have.

What’s the best way to ask someone on a date?

Make a specific, low-pressure invitation that’s easy to say yes or no to. Include what activity, when, and where. Example: “Want to check out that farmers market together this weekend?” Avoid vague suggestions like “hang out sometime” that require them to figure out what you mean.

How do you ask a girl out at work or school?

Keep it professional and low-pressure. Reference your existing conversations: “I’ve really enjoyed our talks. Want to continue this over coffee sometime this week?” Respect workplace boundaries and handle any response gracefully to maintain professionalism.

Should you ask someone out over text or in person?

Ask in person if you see them regularly. Only use text if you don’t interact face-to-face often. In-person asking shows confidence and allows you to read their reaction better. It also feels more genuine and thoughtful than hiding behind a screen.

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Internal links:

• First Date Ideas That Work
• How to Flirt Naturally: Learn to build romantic tension through playful conversation
• Building Social Confidence: Develop unshakeable confidence in social situations
• Reading Social Signals: Master the art of reading interest and attraction cues
• Art of Charm social skills assessment: Discover your current social skills level
• Dating With Social Skills: Complete guide to dating success through authentic connection

External citations:

• Psychology of Rejection and Social Pain
• Communication and Relationship Initiation
• Social Anxiety and Dating Research

The post How to Ask Someone Out: 5 Confident Scripts That Actually Work appeared first on The Art of Charm.

How to Flirt: The Complete Guide for Men Who Overthink It

Effective flirting requires calibration and signal reading, not memorizing lines or trying to be smooth. Most men struggle because they treat flirting like a performance instead of reading the other person’s cues and responding naturally to their energy and interest level.

You’re probably overthinking this.

I know because most guys who struggle with flirting aren’t struggling because they don’t know what to say. They’re struggling because they’re treating flirting like a performance instead of a conversation.

Flirting isn’t about having perfect lines or smooth delivery. It’s about calibration. Reading signals and responding naturally.

What I’ve found working with guys who think they’re “bad at flirting”: they’re usually fine at flirting. They just don’t recognize when they’re doing it.

What Flirting Actually Is

Most people think flirting is about being charming or witty or smooth. Those things can be part of it, but they’re not the foundation.

Flirting is mutual playfulness with romantic undertones.

That’s it.

It’s when two people acknowledge attraction through teasing, banter, and subtle physical cues. It’s a collaborative dance where both people participate.

The key word there is “mutual.” You can’t flirt with someone who isn’t flirting back. You can only hit on them, which is completely different.

One of my clients came to me convinced he was terrible at flirting. He’d been trying to be charming and witty with women who clearly weren’t interested. Then he’d get frustrated when his “flirting” didn’t work.

“Maybe they’re just not into me,” he said.

Exactly. That’s the point.

Flirting only happens when there’s mutual interest. Your job isn’t to create interest where none exists. Your job is to recognize interest when it’s there and respond appropriately.

The Overthinking Problem

Where most guys mess up: they overthink the mechanics instead of paying attention to the signals.

They’re so focused on what they’re going to say next that they miss whether she’s actually engaged. They memorize conversation starters but don’t know how to read if someone wants to be started with.

I think oftentimes the guys who struggle most with flirting are actually the most socially aware guys. They’re just directing that awareness inward instead of outward.

Instead of thinking “Is she enjoying this interaction?” they’re thinking “Am I being weird? Do I sound stupid? Is this working?”

The irony is that the answer to those questions is written all over her face and body language. You just have to look.

Someone close to me used to do this constantly. He’d have great conversations with women, they’d be laughing and engaged, and then he’d text me afterward asking if he’d been awkward.

“Did you see her lean in when you were talking?” I’d ask.

“Yeah.”

“Did she laugh at your jokes?”

“Yeah.”

“Did she ask you questions about yourself?”

“Yeah.”

“Then you weren’t awkward. You were flirting, and she was flirting back.”

Being Flirty: Reading the Signals

Before you worry about what to say, learn to recognize when someone’s open to flirting with you.

These signals aren’t complicated. They’re the same things you do when you’re interested in someone:

She maintains eye contact. Not just polite glances, but actual sustained eye contact during conversation.

She mirrors your energy. If you lean in, she leans in. If you lower your voice, she does too. If you tease her, she teases back.

She touches you casually. A hand on your arm when she’s making a point. A playful push when you say something funny.

She asks personal questions. Beyond “What do you do?” She wants to know about your interests, your background, your opinions.

She creates opportunities to spend more time together. “Oh, you like that band? They’re playing next week.” “There’s this great coffee place I’ve been wanting to try.”

Notice something about that list? None of it requires her to explicitly say “I’m interested in you.” Interest is communicated through behavior, not declarations.

One of my clients was convinced this woman at his gym wasn’t interested because she never directly said so. But she always positioned herself near him during workouts. She asked about his training routine. She suggested they try a new class together.

“Maybe she’s just being friendly,” he said.

Maybe. Or maybe she’s flirting and waiting for you to flirt back.

Calibration: The Real Skill

What separates good flirting from awkward hitting on people: calibration.

Calibration means adjusting your approach based on how the other person responds. If they lean in, you can be more playful. If they step back, you dial it down. If they laugh at your teasing, you can tease more. If they seem uncomfortable, you shift to regular conversation.

This is a skill most people develop naturally, but overthinking can mess it up.

Let me show you what calibrated flirting looks like:

You: “That’s a really interesting way to organize your bookshelf.” (light teasing)

Her: (laughs) “Don’t judge my system. It makes perfect sense to me.”

You: “I’m not judging. I’m impressed. Alphabetical is for amateurs. Emotional categorization is advanced.” (escalating the playfulness because she engaged)

Her: “Exactly! This person gets it.”

You: “Finally, someone who appreciates my sophisticated literary analysis.” (continuing the mutual teasing)

See how that works? You started with light teasing, she responded positively, so you escalated slightly. She kept engaging, so you kept the energy going.

Compare that to what happens when someone doesn’t calibrate:

You: “That’s a really interesting way to organize your bookshelf.” (light teasing)

Her: “Oh, it’s just however they fit.” (deflecting, not engaging with the playfulness)

You: “Come on, there has to be some system. Are you one of those people who organizes by color?” (pushing forward despite her lack of engagement)

Her: “Not really.” (shorter response, wanting to end this topic)

You: “I bet you’re secretly super organized and this is all an act.” (still not reading that she’s not interested in this type of conversation)

That’s not flirting. That’s pestering.

The difference is paying attention to how she responds and adjusting accordingly. When someone deflects your playfulness twice in a row, switch to regular conversation. Maybe she’s not in a flirty mood. Maybe she’s not interested in you that way. Maybe she just doesn’t like being teased about her bookshelf.

All of that is fine. Good flirting respects boundaries.

The Art of Playful Teasing

When the signals are there and she’s engaging, playful teasing is the heart of flirting.

But there’s a right way and a wrong way to tease.

Good teasing is about something she clearly doesn’t mind being teased about. Her quirky habits. Her strong opinions. Her competitive streak. Things she probably teases herself about.

Bad teasing hits on insecurities, appearance, or anything she’s clearly sensitive about.

Test: would she tease her best friend about this same thing? If yes, it’s probably fair game. If no, avoid it.

Some examples of good teasing:

“You’re one of those people who plans their plans, aren’t you?”

“Let me guess, you’re the type who has strong opinions about pineapple on pizza.”

“I can tell you were definitely a rule-follower in school.”

These work because they’re about personality traits, they’re said with warmth, and they give her easy ways to respond playfully.

Bad teasing sounds like:

“You’re really short.” (appearance-based, not playful)

“You seem like you’d be high maintenance.” (negative judgment)

“Bet you’re one of those crazy cat ladies.” (stereotype, potentially offensive)

The difference is obvious when you see it written out, but in the moment, guys often default to whatever pops into their heads.

Simple rule: if you wouldn’t say it to your sister, don’t say it to someone you’re flirting with.

Physical Flirting: Reading and Responding

Flirting isn’t just verbal. A huge part of it is physical. Not sexual touching, but casual, playful contact.

But physical flirting requires even more calibration than verbal flirting. You have to pay attention to how someone responds to each level of contact.

It usually progresses like this:

Level 1: Incidental contact. Your hands brush when you’re both reaching for something. Your shoulders touch when you’re looking at the same phone screen.

Level 2: Brief, casual contact. A hand on her arm when you’re making a point. A playful push when she says something funny.

Level 3: Longer contact. Your hands linger when you hand her something. You keep your hand on her arm while you finish your sentence.

Level 4: More intimate contact. Playing with her hair. Touching her face. Sustained contact during conversation.

The key is to pay attention to how she responds at each level. Does she maintain the contact or pull away? Does she reciprocate or create distance? Does she seem comfortable or tense?

One of my clients was worried about “making a move” because he didn’t know if a woman was interested. I asked him what had happened when he’d touched her arm during their conversation earlier.

“She didn’t move away,” he said.

“Did she touch you back?”

“Yeah, she put her hand on my shoulder when she was laughing.”

“Then she’s probably comfortable with physical contact from you.”

It’s not complicated. People show you how they feel through their responses. You just have to pay attention.

Common Overthinking Traps

Let me address the specific ways overthinking sabotages flirting:

Trap 1: Scripting Conversations

You plan what you’re going to say, how she’ll respond, what you’ll say next. Then when the conversation doesn’t go according to script, you panic.

Flirting is improvisation, not theater. You can’t script authentic playfulness.

Trap 2: Analyzing Every Response

She laughed at your joke. What does that mean? Was it a real laugh or a polite laugh? Does she laugh at everyone’s jokes?

Stop. You’re going to analyze yourself out of what could be a fun interaction.

Trap 3: Waiting for Certainty

You want to be 100% sure she’s interested before you flirt back. But flirting is how you figure out if someone’s interested. It’s not something you do after you know.

Trap 4: Comparing Yourself to “Natural” Flirts

You see guys who seem effortlessly charming and assume you’ll never be like that. But those guys probably started as overthinking as you. They just got more practice.

Flirting is a skill. Like any skill, you get better by doing it, not by thinking about it.

Flirting Tips for Guys: Specific Scenarios

Let’s get practical. Common situations and how to handle them:

At a Coffee Shop

Instead of: “Excuse me, what are you reading?”

Try: (Glancing at her book) “Good choice. That author knows how to make you miss your stop on the subway.”

Why it works: You’re demonstrating knowledge while creating an opportunity for her to share an experience. If she’s read other books by the same author, you have something to talk about.

At a Party

Instead of: “So how do you know the host?”

Try: “Let me guess, you’re the person everyone comes to for party planning advice.”

Why it works: It’s a playful assumption that gives her an easy way to correct you or play along. Either response leads to conversation.

At the Gym

Instead of: “Are you using that machine?”

Try: “I’m impressed. That’s the one machine I pretend to understand but secretly have no idea how to use.”

Why it works: Self-deprecating humor that gives her a chance to help or relate. Shows confidence because you’re admitting you don’t know something.

Online/Dating Apps

Instead of: “Hey, how’s your week going?”

Try: “Your profile says you’re into hiking. Please tell me you’re not one of those people who considers a walk around the block a nature experience.”

Why it works: References something specific from her profile and uses gentle teasing to start a playful conversation.

Notice the pattern in all these examples. You’re not asking for information. You’re making playful observations that invite response.

Reading Micro-Signals: The Advanced Level

Once you get comfortable with basic flirting, you can start paying attention to more subtle signals. These are the micro-expressions and body language cues that tell you exactly how someone’s feeling in real time.

Does she maintain eye contact when you’re talking but look away when you pause? She’s interested but maybe a bit nervous.

Does she lean in when you’re speaking quietly? She wants to be closer to you.

Does she play with her hair or jewelry while you’re talking? She’s either nervous (good nervous) or bored (bad nervous). You can tell the difference by her overall engagement level.

Does she mirror your speech patterns? If you speak slowly, does she slow down too? If you use certain words or phrases, does she start using them? Mirroring is a strong sign of rapport.

These signals matter because they tell you not just whether someone’s interested, but how interested they are and what they need from you in the moment.

If someone’s nervous, you might slow down and be extra warm. If someone’s energetic, you might match their energy. If someone seems distracted, you might change topics or suggest moving to a quieter location.

This level of calibration is what separates good flirters from great ones. It’s also what makes someone attractive in general. People are drawn to others who can read situations and respond appropriately.

This is the kind of social intelligence I work on with my private coaching clients. We start with basic conversation skills, but we end up developing the ability to read people and create connection in any situation.

When Flirting Turns Into Something More

Good flirting creates momentum. If you’re both engaged and the energy is building, you need to know how to escalate.

This is where a lot of guys freeze up. They can flirt, but they don’t know how to transition from flirting to actually making plans or taking things to the next level.

The key is to stay calibrated even as you escalate.

Low-pressure escalation: “I’m checking out this new coffee place tomorrow. Want to join me?”

Medium-pressure escalation: “I’d like to take you to dinner sometime. Are you free this weekend?”

Higher-pressure escalation: “I’m really enjoying talking with you. Let’s get out of here and grab a drink somewhere quieter.”

Notice how each of these gives her an easy way to say yes or no without making things awkward. You’re being direct about your interest while respecting her ability to choose.

The escalation should feel natural based on how well the flirting has been going. If she’s been highly engaged, laughing at your jokes, and creating physical contact, a more direct approach makes sense. If the energy has been good but more subtle, start with something lower-pressure.

What to Do When It Doesn’t Work

Sometimes you’ll read the signals wrong. Sometimes someone will seem interested but then not be available. Sometimes the flirting will be going well and then suddenly fizzle out.

This is normal. It doesn’t mean you’re bad at flirting. It means you’re human.

The important thing is to handle rejection gracefully. If someone’s not interested, respect that immediately. Don’t try to convince them. Don’t ask why. Just accept it and move on.

“No worries, it was great talking with you anyway.”

That’s it. Don’t make it weird. Don’t take it personally. Don’t analyze what went wrong.

Sometimes people aren’t available for reasons that have nothing to do with you. Sometimes they’re in relationships. Sometimes they’re dealing with personal stuff. Sometimes they’re just not in the mood to meet new people.

Learning to handle rejection well actually makes you more attractive because it shows confidence and emotional maturity.

Building Your Flirting Skills

Like any skill, flirting gets easier with practice. But you don’t need to practice on dates or in high-pressure situations.

You can practice being playful with the barista when you order coffee. You can practice teasing your friends. You can practice reading people’s responses in low-stakes conversations.

The goal is to make playfulness and social calibration natural parts of how you interact with people. When those skills are automatic, flirting stops being something you turn on and off. It becomes something you do naturally when there’s mutual interest.

Start small. Pay attention to how people respond to your jokes. Notice when someone leans in during conversation. Practice adjusting your energy based on the other person’s mood.

These skills will make you better at flirting, but they’ll also make you better at all social interactions. You’ll become someone people enjoy talking to because you know how to read the room and respond appropriately.

You’ll become someone who creates connection instead of just hoping for it.

The Confidence Connection

Most guys miss this: confidence isn’t something you need before you can flirt well. Confidence comes from flirting well.

Every positive interaction builds your belief that you can connect with people. Every time someone laughs at your joke or responds well to your teasing, you get a little more comfortable being playful.

Every time you read someone’s signals correctly and respond appropriately, you trust your social instincts a little more.

This creates a positive cycle. You get better at reading people, which makes your interactions more successful, which makes you more confident, which makes you willing to take slightly bigger social risks, which makes you even better at connecting with people.

The guys I work with who transform their social lives don’t just learn techniques. They build genuine confidence through repeated positive experiences.

You probably already have more social skill than you realize. You just need to start trusting it and using it more consistently.

The best way to start is to pay attention to the signals people are already sending you. Notice when someone’s enjoying your conversation. Notice when they’re not. Start adjusting based on what you observe.

You don’t need perfect lines or smooth delivery. You just need to be present enough to see what’s actually happening in your interactions instead of being lost in your own head.

Most of the time, that’s enough.

Want to know how well you read social signals and create attraction naturally? Test your flirting skills and discover what’s working and what to improve when it comes to reading people and building romantic tension.

—

Frequently Asked Questions

How do you flirt without being awkward?

Focus on calibration – reading how the other person responds and adjusting accordingly. Start with light, playful comments and escalate only if they respond positively. Pay attention to their body language and energy level rather than focusing on what you’re going to say next.

What are the signs someone is flirting with you?

They maintain eye contact, mirror your energy, touch you casually, ask personal questions, and create opportunities to spend more time together. They engage with your playfulness rather than deflecting it. Most importantly, they reciprocate the playful energy you’re putting out.

How do you flirt over text?

Use playful teasing, reference specific details from your conversations, and make observations rather than asking interview-style questions. Keep the energy light and engaging while being responsive to their texting style and response time. Avoid being too available or intense.

What’s the difference between flirting and being friendly?

Flirting includes playful teasing, romantic undertones, and mutual acknowledgment of attraction. Friendly conversation lacks the playful tension and romantic subtext that characterizes flirting. Flirting has an energy of “what if” that friendship doesn’t.

How do you know if flirting is working?

She engages with your playfulness, reciprocates teasing, maintains or increases physical contact, asks questions about you, and creates opportunities to continue the interaction or meet again. You’ll feel the energy building rather than having to work to maintain it.

What are some good flirting tips for guys?

Read her signals before escalating, use playful teasing about personality traits (not appearance), calibrate based on her responses, be genuinely present in the conversation, and handle rejection gracefully. Focus on creating mutual enjoyment rather than trying to impress.

—

Internal links:

• Building Social Confidence: Develop unshakeable confidence in social situations
• Reading Social Signals: Master the art of reading people and social cues
• Art of Charm social skills assessment: Discover your social skills strengths and weaknesses
• First Date Conversation Tips: Turn great flirting into successful dates
• How to Ask Someone Out: Transition from flirting to actually making plans
• Social Skills for Dating: Complete guide to dating success through social intelligence

External citations:

• Psychology of Flirting Research
• Nonverbal Communication Studies
• Social Calibration and Rapport

The post How to Flirt Without Being Awkward: 9 Pro Tips (2026) appeared first on The Art of Charm.

• Your personality is your X-factor. If you’re bored by your own life, you can’t expect someone else to be excited by it. Stop hiding behind work and start showcasing the passions and humor that make you uniquely you.
• Confidence is like a building that needs constant maintenance. You can’t flip a switch and become confident overnight. Build it through goals, exposure, and experience — one small win at a time.
• Social proof makes you instantly more attractive. Having a vibrant social circle signals to potential partners that other people find you worth knowing. Skip the apps and build a real network first.
• Technology is making us socially awkward. We’re becoming better at talking to computers than people. The cure is deliberate practice with real humans in real situations.
• Stop seeking attention and approval — start giving value. High-value people give attention, approval, and acceptance. Low-value people constantly seek it.

The Dating Crisis No One Wants to Talk About

Here’s a stat that should terrify every young man reading this: only 30% of men under 30 identify as being in a relationship. That means 70% of young men are single right now.

This isn’t just an American problem. It’s happening in Japan, China, Europe — every advanced country is seeing the same trend. Young men are opting out of dating entirely, and those who are trying are struggling more than ever.

The result? A loneliness epidemic that’s destroying men’s health and happiness. A massive 2020 study of over 46,000 people across 240 countries found that “the most vulnerable to loneliness were younger men living in individualistic cultures.”

“Younger men were more lonely than middle-aged men and middle-aged men were more lonely than older men. And worst of all, it was in individualistic cultures like ours, the West.”

So what’s happening? Technology was supposed to connect us, but it’s actually making us worse at connecting. We’re spending more time talking to computers than people. We’re segregating ourselves into online bubbles where everyone thinks like us. And we’re choosing easy digital entertainment over the hard work of building real relationships.

The good news? There are three attraction triggers that, when you understand them, will set you apart from the 70% of men who are struggling. These aren’t pickup tricks or manipulation tactics. They’re fundamental traits that make you genuinely attractive to both romantic partners and friends.

Why Your Personality Has Been Hijacked by Your Career

The first attraction trigger is showcasing your personality. And for most men, this is where everything falls apart.

Think about it: you work 50+ hours a week. You’re on Slack 24/7. You have to be buttoned up, analytical, and professional in every interaction. When do you get to be fun? When do you get to show your sense of humor? When do you get to talk about the things you’re actually passionate about?

The answer for most men is: never. And that’s why they’re boring on first dates.

“If you don’t have personality, you’re not gonna be able to stand out on the apps. You’re not gonna be able to AI your way out of that conversation, that first date. That personality is the first step to setting you apart from everyone else.”

Brandon learned this the hard way. He was a lawyer going on plenty of first dates but getting zero second dates. Why? Because all he could talk about was work. The solution wasn’t more dating apps or better photos — it was rediscovering his passion for mountain biking.

After joining a local mountain biking group, Brandon suddenly had stories to tell. He had weekend plans that weren’t just Netflix. And for the first time, he saw a woman light up when he mentioned what he was doing that weekend.

Fast forward a few months: Brandon has a girlfriend who he introduced to mountain biking on their fourth date.

The Two Personality Pitfalls That Sabotage Every First Date

When men realize they need to “show more personality,” they usually swing to one of two extremes — both of which backfire spectacularly.

Pitfall #1: Going into your head. You overthink every word, analyze every reaction, and end up saying nothing interesting because you’re too busy planning what to say next.

Pitfall #2: Coming out guns blazing. You try to be the funniest guy in the room, crack constant jokes, and overwhelm the other person with your “personality.”

Both approaches fail because they’re driven by the wrong motivation. You’re either seeking attention because you’re attention-starved, or you’re seeking approval because you need validation.

“If you’re using your personality to seek attention or you’re using your personality to seek approval, it’s actually not a personality that people are gonna wanna spend a lot of time around.”

Real personality isn’t about performing. It’s about sharing your world with someone and being genuinely curious about theirs. It’s about showcasing your passions, your sense of humor, and your perspectives — while also drawing out what makes them unique.

How to Rebuild Your Sense of Humor (Yes, It’s Trainable)

Here’s something most men don’t realize: your sense of humor can be strengthened like a muscle. Your favorite comedians don’t just walk on stage and wing it. They test their material in small rooms, bomb repeatedly, and figure out what actually gets laughs.

The solution? Improv.

Improv teaches you to be funny in a way that gets people laughing with you, not at you. It breaks you out of the over-analytical mindset and teaches you to be present in conversations. Most importantly, it teaches you that humor comes from being curious about other people, not from trying to be the star of the show.

The best improv principle for dating: “The answer is always in the other person.” If you’re not listening or taking interest in other people, of course you’re going blank — you have nothing to work with.

The Science of Empathetic Listening (And Why Women Find It Irresistible)

There’s a study by Davis and Oathout that tracked romantic relationships over time. They found that empathy — particularly the ability to pick up on and respond to emotional cues — was “positively associated with satisfaction in romantic relationships” and helped maintain those relationships long-term.

Think about it: if you meet someone for the first time and they’re tuned into your needs, they notice when you’re thirsty and offer to get you water, they pick up on your excitement about something and ask follow-up questions — you instantly feel like you can trust them.

“If I meet you at a social event for the very first time, and I get the sense that you’re tuned to my needs, that shows me that I can trust this guy. We’re off to a good start here.”

The problem? Most men are so focused on what they’re going to say next that they miss these emotional cues entirely. They’re having conversations with themselves instead of with the person in front of them.

The fix is simple: ask questions, actually listen to the answers, and make statements based on what you heard. When someone feels heard by you, they become curious about you. That’s when real connection happens.

Why Confidence Isn’t a Switch You Can Flip

The second attraction trigger is confidence. But here’s what most men get wrong: confidence isn’t something you just decide to have. It’s something you build.

Think of confidence like a building. If you construct a building and then abandon it, gravity will do its job and it will eventually fall down. Your confidence works the same way. If you have an experience that builds your confidence but then never challenge yourself again, that confidence will slowly disappear.

“Confidence is no different than that building. If you go out and have an experience that gives you more confidence in a certain area, if you don’t do that thing again, if you don’t have that experience again, that confidence will slowly wane.”

This is why there’s no “one thing” you can do to instantly become confident. It’s about the process. It’s about having a growth mindset that allows you to take on challenges, fail, learn, and try again.

The Two Confidence Traps That Make You Less Attractive

When it comes to showcasing confidence, most men fall into one of two traps:

Trap #1: Holding back to avoid seeming arrogant. You’re so afraid of coming across as bragging that you don’t share anything about yourself. You appear weak and needy.

Trap #2: Overcompensating with braggadocious behavior. You swing the other way and try to impress everyone with how successful/funny/cool you are. You come across as insecure and try-hard.

Both approaches fail because they’re reactive. When you’re not confident, you’re reacting to your environment, trying to become whatever you think you need to be in that moment.

Confident people do the opposite: they bend the environment to them. They have a strong sense of their values, their principles, and their philosophy. They’re led by intentionality, not by the reactions of others.

The Confidence Training Dojo: Start Small, Build Big

One of the biggest mistakes men make is thinking they need to go from zero to hero overnight. You don’t throw yourself into the deep end — you build up gradually.

Take Dan, a client who moved to a new country where he didn’t speak the language fluently. He was petrified of talking to people. Instead of forcing him to approach strangers immediately, his coach started with smaller challenges:

First: lie down on a sidewalk in a busy area for 30 seconds. Just to confront that inner critic about what people might think.

Next: put on headphones and dance in a park by himself for a few seconds.

Dan’s realization: “If I can lie down on a sidewalk in the city, if I can dance in the park all by myself with people staring at me, talking to people is easy.”

“This was awesome. My heart was racing like crazy, but this was really awesome. I had people smile at me when they walked by.”

From there, Dan started approaching everyone — people with headphones, people in groups, tourists. Eventually, he organized his own confidence-building workshop and got 15 people to show up.

The lesson: confidence is built through small exposures to discomfort, not giant leaps.

Why Your Non-Existent Social Circle Is Killing Your Dating Life

The third attraction trigger is the most overlooked: preselection, or social proof.

If you’ve neglected building a network, if you’ve neglected your social life, if all you do is work and then try to find dates on apps, you’re not going to be attractive. Here’s why:

When other people find you interesting enough to be their friend, when they invite you to things, when they want to spend time with you, you naturally become more interesting to potential romantic partners.

This isn’t manipulation or a trick. It’s basic human psychology. We look to others for cues about how to evaluate someone. If no one else seems interested in you, why should a potential date be?

“When other people are interested in having you as a friend, are interested in being a connection of yours, are interested in you, you naturally become more interesting to other people.”

Brad learned this after his divorce. He was going on first dates but immediately suggesting second dates for that same weekend. Why? Because he had nothing else going on. No social circle, no activities, no life outside of work and dating.

The solution: Brad signed up for salsa lessons (something he’d always wanted to try). He made friends in class. One couple started hosting pizza nights on weekends. Suddenly Brad had stories to tell, weekend plans, and a co-ed social circle.

The result? He became unavailable for immediate second dates, which made him more attractive. He had interesting things happening in his life, which made him more interesting. And he had social proof from his new friends, which signaled to dates that he was worth knowing.

How to Become a High-Value Person Without Getting Taken Advantage Of

Building a social circle requires being what we call a “high-value person” — someone who gives attention, approval, and acceptance rather than constantly seeking it.

But here’s the fear most men have: “What if I give and give and never get anything back? What if people take advantage of me?”

The solution is learning to be effective and efficient in your communication and value-giving. You want to connect with people genuinely, but you also want to recognize when your investment isn’t being reciprocated.

According to research by Robert Cialdini on social influence, when you’re new to a social setting and a few respected people treat you well, everyone else follows suit. This is informational social influence — people look to others for cues about how to treat you.

The key is finding the right people to invest in — people who appreciate genuine connection and will reciprocate your efforts to build real relationships.

Why Apps Are Making You More Needy (And What to Do Instead)

Here’s the trap most single men fall into: they focus solely on romantic relationships. They download dating apps, go on first dates, and when those don’t lead anywhere, they download more apps.

This approach fails for multiple reasons:

• You become needy because dating is your only social outlet
• You have nothing interesting to talk about because you have no life outside work and dating
• You lack social proof because potential partners see that no one else finds you worth knowing
• You put too much pressure on each date because it’s your only option

The solution isn’t better dating strategies — it’s building a life worth sharing. Join activities you’re genuinely interested in. Make friends. Develop hobbies. Create a social circle where you can practice conversation skills in low-pressure environments.

When you have a vibrant social life, dating becomes easier because you’re no longer desperate. You have other options, other sources of fulfillment, and interesting things happening that potential partners want to be part of.

The Technology Trap That’s Killing Your Social Skills

We’re becoming better at talking to computers than to people. We communicate through asynchronous text messages, Discord chats, and Slack channels. We consume entertainment passively through Twitch streams and YouTube videos.

All of this creates a vicious cycle: because we have easy digital alternatives, we don’t practice real social skills. Because we don’t practice social skills, social situations become more intimidating. Because social situations are intimidating, we retreat further into digital alternatives.

“We’re becoming more adaptive talking to computers than talking to people due to asynchronous communication. And it’s funny because when we first started this company 17 years ago, communication has not gotten any better. In fact, it has gotten worse.”

The internet also segregates us into bubbles of people who think exactly like us. Your jokes work in your Discord because everyone shares your worldview. But that doesn’t prepare you for connecting with people who are different from you — like potential romantic partners.

The cure is deliberate practice with real humans in real situations. Take classes, join groups, go to networking events. Put yourself in environments where you have to navigate different personalities and perspectives.

How to Journal Your Way to Better Conversations

You can’t improve what you don’t measure. After every meaningful conversation, write down what you learned about the other person. This forces you to become a better listener.

Start a gratitude journal — write down five things you’re grateful for every morning. When you stop for a week, you’ll notice the difference immediately in how you show up in conversations.

Set small, measurable goals: “This week I’ll talk to three strangers.” Next week, five. Next week, seven. Track your progress. Before long, the thing that terrified you will seem absurd.

“Write it down and celebrate the wins and watch yourself move forward. If you don’t write it down, you don’t give yourself credit for it, and you keep labeling yourself as awkward and you never grow.”

The Epidemic Solution: Stop Competing, Start Building

With 70% of young men single, this isn’t just a personal problem — it’s a cultural crisis. But it also represents an enormous opportunity.

While most men are retreating into digital entertainment and apps, you can set yourself apart by developing these three attraction triggers:

1. Showcase your personality through genuine interests, improved humor, and empathetic listening
2. Build real confidence through goal-setting, exposure therapy, and consistent growth challenges
3. Create social proof through a vibrant network of genuine friendships and shared activities

These aren’t pickup tricks or manipulation tactics. They’re the fundamental skills that make you genuinely attractive to both romantic partners and friends. They cure loneliness, improve your career prospects, and make you the kind of person others want to be around.

The technology that was supposed to connect us has isolated us instead. But that isolation can be reversed. It just requires doing the work that most men aren’t willing to do: getting offline, getting uncomfortable, and getting real.

Related Reading

• How to Stop Being Socially Awkward: A Complete Guide
• How to Build Confidence: The Complete Guide
• How to Build a Social Circle: The Architecture of Intentional Friendship
• The Psychology of Attraction: What Makes Someone Irresistible

Frequently Asked Questions

Why are 70% of young men single?

Technology has made us better at communicating with computers than people. We’re working longer hours, spending more time in digital entertainment, and segregating ourselves into online bubbles. This has stunted the development of personality, confidence, and social circles — the three key attraction triggers that make men genuinely attractive to potential partners.

How do I show personality without being overwhelming?

Focus on showcasing your world while being curious about theirs. Share your passions and interests, but ask questions and listen actively. Avoid seeking attention or approval — instead, aim to create genuine connection through mutual discovery. The goal is to light each other up, not to perform.

Can confidence really be built, or are some people just naturally confident?

Confidence is like a building that requires constant maintenance. It’s built through setting goals, gaining experiences, and handling challenges. Start small — even simple exposure exercises like dancing in public for 30 seconds can help you overcome your inner critic and build genuine confidence over time.

Why is having a social circle important for dating?

Social proof makes you instantly more attractive. When other people find you interesting enough to be their friend, potential romantic partners see that you’re worth knowing. Plus, having a vibrant social life means you’re not needy or desperate in dating situations — you have other sources of fulfillment and interesting things happening in your life.

Should I delete dating apps and focus on real life instead?

Dating apps can work, but not if they’re your only strategy. Build a real social circle first through activities you genuinely enjoy. This gives you stories to tell, confidence to showcase, and social proof to leverage. When you have a full life, dating apps become just one option among many, not your desperate last resort.

Ready to discover your personal attraction style? Take the Influence Index Quiz — it reveals exactly where your social skills stand and how to level up your game.

The post 3 Science-Backed Attraction Triggers That Actually Work | Toolbox appeared first on The Art of Charm.

In today’s episode, we cover self mastery with Connor Beaton. Connor is the founder of ManTalks, a TEDx speaker, runs a top ranked podcast called ManTalks, and is the author of Men’s Work: A Practical Guide to Face Your Darkness, End Self-Sabotage, and Find Freedom. 

We are facing a crisis of masculinity, so what can we learn from other cultures when it comes to helping and encouraging boys to become responsible and powerful men, why is it important for men to have strong friendships with other men, and what are modern men missing that lead them to fail in relationships?

What to Listen For

• Introduction – 0:00
• Why are initiation rituals important for men and what price is society paying for not having initiation rituals?
• Why do men abuse power and what can we do to prepare our sons so they don’t abuse power when they become men?

• Initiation Rituals – 10:56
• Why do cultures across the planet use initiation rituals for young boys to enter into manhood?
• How does your self-talk hold you back from being the person you want to be and how do you improve it?
• Why is it important to have groups solely for men to be men and talk about men’s issues?

• Men and Self Development – 26:14 
• What is the most important thing men should focus on to achieve and maintain their happiness and fulfillment in life?

• The Secret to Non-Neediness in Relationships – 40:05 
• What are men lacking in their lives that lead them to be needy in romantic relationships, causing those relationships to fall apart?

Initiation rituals have been used throughout history to help transition young boys into manhood. These rites of passage can teach us many things, but the most salient theme that remains is the need for men to face failure and powerlessness so as to enter manhood with a strong sense of self and humility. With positive self-talk we can stop ourselves from believing any false disclosures we face and learn how to think positively and productively. It is also important that men find male-only spaces where they can be men and talk about their issues. 

A Word From Our Sponsors

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But there’s something you can do about it.

After coaching over 10,000 clients including military special operators and Fortune 500 executives we’ve learned a thing or two about what it actually takes to grow your network. In fact, over 90% of the amazing guests on this show are from referrals in our personal networks.

We’ve packaged our best insights inside a course called, Social Capital. And, as a thank you for being a podcast listener, we want to give you this training for FREE to start 2023.

To get your hands on this training and immediately start improving your relationships, go to theartofcharm.com/sc

Do you LOVE the toolbox episodes? Did you know that every week we give a LIVE mini-toolbox lesson inside our Private Facebook Group? Best of all it is FREE to join. Join today and get access to all of our live training and level up your communication, leadership, influence and persuasion skills. With 14,000 members it’s a great place to network, learn and overcome any obstacle that’s in your way.

Running out of things to say in conversation… and still struggling to get people interested in you? That’s an uncomfortable position to be in. Don’t want to risk getting tongue-tied and screwing things up the next time you meet someone? Check out Conversation Magic now to make sure you don’t crash and burn. With our bulletproof formula, you’ll be flirting up a storm, sparking fun and engaging conversations, and making high-value friends anywhere!

Resources from this Episode

• Men’s Work: A Practical Guide to Face Your Darkness, End Self-Sabotage, and Find Freedom by Connor Beaton
• Connor Beaton’s website
• Connor Beaton on Instagram

Check in with AJ and Johnny!

• AJ on Instagram
• Johnny on Instagram
• The Art of Charm on Instagram
• The Art of Charm on YouTube
• The Art of Charm on TikTok

The post Facing Your Darkness To Reach Your Full Potential w/ Connor Beaton appeared first on The Art of Charm.

In today’s episode, we cover healthy relationships and finding the right partner with Dr Yael. Dr Yael is a licensed clinical psychologist, assistant professor at Brown University, and writer about parenting, work, and relationships.

A healthy relationship takes work, but how do you know what relationships are worth the work, is moving in together a good test for the relationship, and how do you reignite passion in a relationship?

What to Listen For

• Introduction – 0:00

• Why did Dr Yael Schonbrun take the Art of Charm Unstoppable program?
• What is the trap many of us fall into in the modern dating world and why are we making it harder to find healthy relationships?

• Value based dating and moving in together – 13:00 
• What questions can you ask to figure out what you want to get out of dating?

• What mindset do you need to avoid if you’re thinking about moving in with someone you’re dating?
• What signs should you look out for when thinking about moving in with someone?

• Looking beyond lust for red flags – 30:40 
• How should you think about lust when you’re actively dating?

• Reigniting passion in a relationship – 44:40 
• What is the foundation for passion in romantic relationships and what can you do to reintroduce it?

• What is the evolutionary need for novelty in romantic relationships?
• How do you know when a relationship is worth ending?

Your relationships require the same work we put into everything else in life. If we go about life acting as if those relationships will always be there, we are bound to lose them. Why should they invest time in us if we’re not willing to invest in them? The first step in developing healthy relationships is making that commitment to invest and following through.

A Word From Our Sponsors

Do you LOVE the toolbox episodes? Did you know that every week we give a LIVE mini-toolbox lesson inside our Private Facebook Group? Best of all it is FREE to join. Join today and get access to all of our live training and level up your communication, leadership, influence and persuasion skills. With 14,000 members it’s a great place to network, learn and overcome any obstacle that’s in your way.

Did you know that you can get the whole Art of Charm catalogue when you subscribe to Stitcher Premium using our link? That’s 15 years of podcasts featuring expert guests and toolbox episodes! Sign up today and use Code “CHARM” to get a free month!

Resources from this Episode

Dr. Yael Schonbrun’s website

Unstoppable Coaching Program

Check in with AJ and Johnny!

AJ on Instagram

Johnny on Instagram

The Art of Charm on Instagram

The Art of Charm on YouTube

The post Dr. Yael Schonbrun | Dos and Don’ts of Modern Dating appeared first on The Art of Charm.

In today’s episode, we cover how to keep the romance in your life fresh.

Unfortunately, many of us believe relationship myths as truth which can set us up for failure, so what are the biggest relationship myths, what else do you need besides love to make a relationship work, and what skills can you start working on today to improve your relationships?

What to Listen For

• The Biggest Relationship Myths – 5:50
• What are the biggest myths surrounding relationships and why do we believe them?
• Why do some people fall in love with falling in love more than they fall in love with actual people?
• How are dating apps making it more difficult for you to find a healthy relationship and what should you do to avoid falling into the swipe life trap?
• What are the 2 human traits that work against us when it comes to dating apps and how do we overcome them?

• The Tools for Strengthening Relationships – 15:45
• What are emotional bids and how can you use them to deepen your relationships?
• What is the DEEP framework and how can you use it to understand the differences between you and your partner?
• What question can you and your partner ask each other to develop actionable goals to be more supportive for one another? 
• What 4 skills can you start working on today to keep your relationship fresh?
• What simple exercise can you implement every day or week to improve the communication in your relationships?
• What are the 3 levels of listening and how can your knowledge of them help you strengthen relationships? 

A long lasting happy relationship requires more than just love. If you don’t have the skills to navigate all of the issues and challenges that inevitably arise from two people spending time together, love won’t simply solve all of your problems. Fortunately, the skills necessary to forge healthy relationships can be taught and learned, but you must be willing to grow.

A Word From Our Sponsors

Share your vulnerabilities, victories, and questions in our 17,000-member private Facebook group at theartofcharm.com/challenge. This is a unique opportunity where everyone — both men and women — celebrate your accountability on the way to becoming the best version of yourself. Register today here!

Resources from this Episode

• Why Emotional Connection Makes or Breaks a Relationship (Episode 719)
• Turning Toward Emotion (Episode 720)
• THIS IS WATER! A speech by David Foster Wallace

Check in with AJ and Johnny!

• AJ on Instagram
• Johnny on Instagram
• The Art of Charm on Instagram
• The Art of Charm on YouTube

The post Toolbox | Why Love Isn’t Enough & the 4 Skills You Need for a Healthy Relationship appeared first on The Art of Charm.

How to attract women with body language

One thing women find creepy in men is when a guy makes eye contact with a woman without ever blinking.

How do you avoid this common mistake men make when it comes to how to flirt with a girl without being creepy? Focus on making the right kind of eye contact. Avoid leering at a woman and focusing on one particular area of her with a hard, intense, unblinking stare. Instead, make women attracted to you right off the bat. Use a soft, relaxed gaze that allows you to take more of her in.

There is one trick to making that kind of charming and inviting eye contact. Smile with your eyes. You know that feeling you get in your eyes after laughing really hard? That is the same feeling you want to recreate when making eye contact with a woman you’ve never met. It projects friendliness and warmth which will get the girl interested in meeting you.

Once you’re comfortable holding eye contact with a woman you you find attractive, then you work on gauging her interest in you via her eye contact.

How to avoid being sleazy with women (with a slight shift in attitude)

Before you even approach a woman, keep something in mind. Make sure you don’t have her up on a pedestal. Looks are just a small piece of what makes women attractive. You’ll never be able to attract women effortlessly if you think beautiful women are out of your league just because they look good.

So ask yourself: what else does she have going for her? Is she fun? Is she caring? Does she have an interesting life?

Having standards like this will take her off the pedestal and automatically ease some approach anxiety. It also helps you come across as a high-value man who is selective and confident with women. Not surprisingly, that will get more women attracted to you. And women are naturally attracted to men who other women cosign for by being in their presence.

Now, there is a trick to how to go about finding the answers to these questions. You don’t want to come out of the gate asking them as that can be overwhelming. Instead, when you first start a conversation with a girl, get the ball rolling with some fun, playful banter. Banter creates a relaxed and safe atmosphere. Then ask questions that will make her qualify herself to you. Questions like:

• What kind of adventures have you been up to lately?
• So what’s your deal?
• What do you do for fun?

By asking qualification questions like this, you challenge her to prove that she’s more than just a pretty face. That kind of challenge will only make you more attractive to the girl – and in itself can be enough to get her chasing you.

What women want in a man

Another thing that turns women off and makes them feel uneasy about a guy is when a guy appears “fake” – when his words and actions are incongruent with who he is and what he’s feeling. On the other hand, women are attracted to a guy who does the opposite, and shows integrity.

Showing integrity is as simple as standing by your thoughts/opinions/feelings – however, many guys slip up here. They think that to get a woman to like you, you need to agree with everything she says. But that’s not the case. A guy who is afraid to disagree with a woman just shows insecurity, neediness, and a lack of integrity. But by sticking to your guns and being willing to disagree with the girl, you actually become more attractive to women. It shows you’re not seeking approval, and that you’re a secure man who has confidence with women.

Here’s an example of what showing the integrity that women find attractive might look like: If you love Schwarzenegger movies and the girl you’re interested in or her friends say his movies are stupid, don’t start backtracking and say you don’t really like them either. Instead, stand up for yourself (and do it with a smile). Use it as an opportunity to have a bit of fun and start some playful banter with the girl. Maybe respond with something like “What!? Don’t you like Schwarzenegger movies? That’s it, this isn’t working out, I want a divorce. You can keep the beach house, but I want the boat. You never used that thing anyway…”

What to say to a girl you don’t know (without being creepy)

One last thing that can creep women out is when a guy is oblivious to social norms. A guy like that might be embarrassing to be with down the road. So she’s not going to be interested in dating him. So when approaching women to make sure you don’t creep them out, demonstrate that you’re a guy who understands social norms – even if you don’t follow them.

For example, meeting women in the daytime is not all that “normal” for many guys. Most guys have too much approach anxiety to approach an attractive girl on the street, subway, grocery store etc. So in situations like this, demonstrate that you understand starting a conversation with a girl you don’t know in the middle of the day is outside the norm… you just don’t care.

If you’re approaching a girl in the daytime then, start the conversation with the girl by saying something like “I know this is a bit weird, but I just wanted to come to meet you”. This shows that you understand the situation and you know you’re doing something out of the ordinary, but you’re confident enough that you don’t give a damn.

If you don’t want to risk getting tongue-tied and screwing things up when you ask her out, check out Conversation Magic to make sure your next date doesn’t crash and burn. With our proven formula, you’ll be flirting up a storm, sparking unforgettable conversations, and attracting the high-quality women you want to date! 

Before you know it, you’ll have to pay attention for the hidden signs she’s falling in love with you.

The post How to Flirt With a Girl Without Being Creepy (Expert Advice) appeared first on The Art of Charm.

There’s something funny about the way we talk about authenticity. We want to learn authenticity. We want to react authentically. Authenticity is something we want to get. We treat being authentic as something we have, as opposed to something we are. Which can keep us from actually developing this trait, since we’re trying to attain something that, by definition, we already have.

If we define authenticity as simply being your true self, then we really shouldn’t have to look for it in the first place. If we’re looking for it, then we’ve already lost it. And that is what we can call the paradox of authenticity.

If you’re trying to be authentic, you’re not being authentic.

So how can we possibly learn to become more authentic?

—

We have to start by understanding why authenticity is so important.

It might seem obvious, but it’s not. After all, we live in a world that thrives on inauthenticity. Traditional jobs run on office politics, the news feeds on false information, celebrities pretend to be real people, brands curate fan pages, even our friends put on nice faces or say what we want to hear to keep us happy. We don’t need to belabor the point, but it’s important to realize how much of our lives are driven by bullshit, which is the lack of authenticity.

But if you think about the moments in your life that are meaningful—I mean truly meaningful—you will always find a degree of realness, of true authenticity. A heartfelt compliment, an honest job review, a great movie, an actually enjoyable first date: these all involve at least some degree of authenticity.

The reason we recognize authenticity is that we’re primed to respond to it. And we’re primed to respond to it authentically. In short, we know it when we see it. And it feels good. It feels true. It feels like something real, which is why it resonates so strongly with us. If we put up with a world that is so often inauthentic, it’s only because we’ve forgotten what real authenticity feels like. But that only makes us hungrier for it, which explains why a politician with even a hint of truth or a speaker who dares to be vulnerable has the power to inspire us.

And when they do—how special! We can probably count those moments on one hand. They’re extraordinary. We feel moved by authentic people, we feel attracted to them. Similarly, we feel attractive when we are being authentic, and when we connect with someone who is authentically engaging with our attractiveness. When we have a killer job interview or a truly special date, what we’re usually saying is that we encountered a moment of mutual authenticity.

Being authentic is also a lot easier. It’s tempting to forget, but being yourself—and being around other people who are themselves—is much easier than pretending, or falsifying, or putting on a social mask, which are common ways to cope with a world that feels false. In fact, it’s inauthenticity that makes pick-up lines, memorized openers and canned responses so attractive. These techniques seem easier, until we discover that they only go so far. They break down as soon as a relationship demands real authenticity, at which point we realize how much easier it would have been to just be ourselves.

So on multiple levels, we’re craving that realness: we want to be authentic, and we want to be around authenticity. The more we try to be something else—what our parents told us we should be, what our jobs demand us to be, what other people seem to think we should be—the more the desire to just be ourselves grows stronger.

If you need any more evidence for why this trait is so important, ask yourself whether you feel better being yourself or pretending otherwise. I think if we’re being honest, it always feels better to be authentic. If it ever feels better to be inauthentic, it’s only because we haven’t quite learned how to be ourselves.

So if authenticity is something we all want, but it’s impossible to have, since it’s something you are and not something you get, then authenticity must be impossible to teach, right?

As I like to say, teaching someone how to be authentic is like teaching someone to be taller. It might even be worse, because no one can fake being taller, but they can definitely fake being authentic. In fact, they do it all the time, as we just discussed.

So how can you learn to become more authentic?

As we’ve already discovered, you can’t. That’s the trap.

What you can do, however, is stop being inauthentic.

And that’s where we’ll begin.

—

If authenticity is the feeling of being your real self, then we can define inauthenticity as the feeling of not being your real self.

That can take many forms: masquerading as someone you’re not, compromising what you feel is right, feeling strange in your own skin, mimicking those around you, or generally feeling like you’re not one with your day-to-day experience.

You might recognize inauthenticity as a kind of pretending. It comes along with feelings of fraudulence, deception, self-consciousness, and the feeling that you need to keep up appearances. For many of us, that describes our work personas. For others, that describes who we are in a relationship.

These patterns can become so ingrained that being authentic seems more uncomfortable than faking it. Once we’ve gotten to that point, we can be pretty sure it’s time for a change.

Now, we should pause here and make an important distinction. At its core, inauthenticity does not feel truly comfortable. But let’s not confuse inauthenticity with discomfort. These are two different things.

For example, you might feel uncomfortable approaching a stranger at a bar. But that doesn’t mean approaching a stranger is inauthentic. You can have your experience of being uncomfortable talking to a stranger while remaining authentic about just how uncomfortable you really are.

In fact, that’s exactly what our residential programs are all about: trying new techniques, feeling the discomfort, and being honest—that is, authentic—about how uncomfortable those techniques can feel at first. Over the program, we work through the self-consciousness, and what felt uncomfortable becomes normal, and what felt inauthentic becomes real.

(By the way, that explains why “flawed” approaches can sometimes work really well. I’ve seen guys walk up to girls, tell them how nervous they are to say hello, and go on to have great conversations. At the very least, they’re not pretending, which frees them up to have a real moment. Humans—women especially—are authenticity lasers: They zero in on that shit. People know when they’re talking to the real thing.)

So remember: Discomfort is good, and is usually a sign that you’re being stretched. You might not normally go up to a stranger in a bar, but that doesn’t mean you’re being inauthentic by trying. As a great Harvard Business Review article explains, moving beyond our comfort zones can make us want to protect our identities by retreating to familiar behaviors and styles—behaviors and styles that don’t actually serve us, that aren’t who we really are deep down.

And that’s a corollary to the authenticity paradox: You can be inauthentic by doing what seems authentic (that is, what feels most comfortable), and you can be more authentic by trying things that feel inauthentic (that is, new thoughts and behaviors that are uncomfortable simply because they’re new).

Crazy, I know. But that’s how our minds can deceive us into avoiding who we really are.

—

So back to the problem: If we can’t try to be more authentic, then how can we become more authentic?

The first step is to stop being inauthentic. That’s how we get around the authenticity paradox.

It’s not that we’re learning how to be authentic, but that we’re un-learning inauthenticity.

And it turns out that un-learning inauthenticity is very doable.

The first step is to notice when it arises.

That’s it. Just notice it.

The moment you catch yourself being inauthentic—saying something you don’t believe, pretending to feel something you’re not—you’ll want to shake it off pretty quickly. The instinct will be strong, because there’s nothing fun or easy about pretending to be something you’re not. At the end of the day, we all just want to get back to being ourselves.

Then, listen to that instinct.

When you feel the bullshit arising, when you feel the discomfort of pretending to be someone you’re not, stop and pay attention.

That might seem obvious, and it is, but this is where most people—even people who are truly committed to becoming more authentic—get stuck. It’s one thing to notice the tendency to be inauthentic. It’s another to admit that it’s happening, right now, in you, and that there’s another way to be.

Next, take a moment and have a laugh.

Seriously. This is important. You catch yourself defending a point of view you might not really hold, or tolerating someone’s toxicity out of obligation, or fighting for a job you don’t really want. Whatever the situation, the moment you catch yourself having an inauthentic moment, stop and enjoy the discovery.

So you were being inauthentic just now—how funny! You forgot who you were for a moment. Now you remember. Well that was weird…

The other day I was on the phone with my partner, and we had just gotten a list of questions from a journalist interested in our company. The questions were a little strange, a little misleading, and totally out of left field. We spent a few minutes discussing them together, trying to come up with good answers, suddenly finding ourselves inarticulate and confused, each of us getting more worked up as we tried harder and harder to find answers to these not-so-great questions.

Suddenly, I stopped.

“I’m kind of stressed out,” I said.

“Me too!” he said.

And in that little moment, everything shifted. We both realized the questions were unhelpful. We both remembered that we totally knew how to talk about our business. And suddenly, we started coming up with new ideas, new talking points—and they were way better than what we were talking about a moment earlier.

I had been drawn in by a situation—in this case, a list of questions—and had quickly forgotten who I was: a guy who loves talking about what he does, who knows AOC inside and out, who’s excited to share our work with other people. I then started pretending to be this other guy who has clever answers to bad questions. That guy wasn’t a very good partner, and the moment I realized it, I knew I had to say something. After we both recognized our frustration and had a laugh, I remembered who I was, and suddenly I knew exactly what to do. I was back to being myself. I was authentic again.

Laughing at yourself in the moment will also help you avoid another tempting trap: Beating yourself up for being inauthentic. That’s not what we’re here to do. (In fact, I’d argue that being hard on yourself is a very inauthentic thing to do.) It doesn’t feel good, because it’s totally unnecessary. You’re human. It’s normal to slip into inauthentic moments. We’ve learned some funny behaviors from the world around us over the years. Sometimes we forget who we are. It’s all good.

Because when you notice the inauthenticity arising…

You just stop, notice it, and accept it…

And enjoy that moment of remembering who you really are…

You’re on your way toward being more authentic.

Which leads us to the last step in the process…

Finally, you have to be willing to put your inauthenticity aside.

That’s a little harder. A lot of us rely on our roles, our beliefs, our positions, our identities. They’re comforting. They’re familiar. They allow us to navigate the world in a safe and predictable way. Putting them down would mean losing something that we’ve been using, probably for a long time.

Because who are you without the persona? What are you going to say if you don’t give the bullshit compliment? Why are you at this party if you don’t know what to talk about? Do you belong in this meeting if you don’t know the answers?

That’s why a lot of what we do here at AOC is a subtractive process. In some cases, we’re here to add things to you—techniques, skills, sensibilities, frameworks. In other cases, we’re here to remove things—limiting beliefs, assumptions, fears, and—as a result—inauthenticity.

Ultimately, you don’t become more authentic by trying to be more authentic (remember the paradox!), but by removing all the other stuff—the hollow statements, the biased beliefs, the silly opinions, the feigned interest, the canned responses, the formulaic answers—that makes up your inauthenticity.

Authenticity isn’t the presence of something, but the absence of everything that isn’t authentic.

Let that sink in. You’re not here to add anything to become more authentic. You’re only here to take away anything that isn’t real. Remember that when you find yourself disconnected from who you really are, and you’ll quickly find a path back to a fun, enjoyable, authentic moment.

Once you put aside your inauthenticity, you’re left with only one option: You have to be yourself. You have no other choice. It’s a little scary, but it’s also liberating.

As Oscar Wilde said:

“Be yourself; everyone else is already taken.”

The post Solving the Authenticity Paradox (How To Be Who You Really Are) appeared first on The Art of Charm.

You know what women find sexy? Among other things, great fathers.

Jordan recently did a podcast with two of our bootcamp alums — both of them single dads — to discuss how the program made them a better man, a better father and a more attractive prospect to women. It was a fascinating look at single dads and dating.

Of course, these three qualities are deeply connected. It can often feel like having a successful family competes with having a successful dating life — there are always trade-offs, for sure — but as we’ve discovered, they can also go hand in hand. After all, the skills, traits and accomplishments required by each of those roles can just as easily reinforce the other.

After diving into this important topic, we discovered some fascinating insights about single dads and dating, and specifically how single fathers can thrive in this arena. Starting with the fact that it’s not just possible to go from being (just) a single dad to a sexy dad, but in some ways easier.

What Science Says About Being a Good Dad

First, let’s talk briefly about what scientific research says about the relationship between parenting skills and attraction. Not surprisingly, they’re closely related, and understanding the connection can make you into a better man and a better partner. Here are the highlights.

1. A good sense of humor and the ability to crack a joke. Joking around with your kids helps them to develop highly attuned social skills, according to a presentation at the Economic and Social Resource Council. In turn, you remain in a playful and social mode, which can make you more social, outgoing and present when you meet new women. One of the first things I teach guys is to make their approaches more light hearted and less serious — just like children do.
2. Clinginess. Clingy parents, as we know, can pass on certain complexes to their kids. That’s what Neil Montgomery, a professor at Keene State University in New Hampshire, has found through his research. The same applies to women. Giving the woman in your life some space, giving her room to want you back — these can nurture attaction. Nothing is going to suffocate a potential relationship and kill attraction faster than being the guy who’s constantly around, demanding attention. The strength and independence (as well as the mystique) that comes with healthy distance is something fathers can appreciate more than others.
3. Compassion. Highly self-critical people tend to be more critical of others — and that’s no fun for anyone. (Dr. Kristin Neff has a whole book on this topic worth checking out.) Being more non-judgmental — something all parents must learn to cultivate — makes you easier to talk to and less critical of the flaws of others. That’s going to go a long way toward making you the kind of guy she wants to open up to and spend time with.
4. A positive attitude. One thing I’m always telling guys about how to talk to girls is to stay positive. Negative energy, as we all know, is a major attraction-killer. It also makes for bad parenting, which is why fathers who are positive can see remarkable results at home and in the dating world. Negative parents, in contrast, tend to have aggressive kids, according to a University of Minnesota study — and probably less-than-fulfilling romantic relationships.
5. Patience and perspective. Romantic relationships require a certain forgiveness and patience that also make for healthy parenting. Practice not getting rattled at home, and watch that patience translate on dates. If a woman you’re dating is being a little difficult — as is bound to happen from time to time — the best thing you can do is maintain your own equanimity. Getting swept up in whatever is agitating her (no matter how well-founded and reasonable it might be) isn’t good for anyone.
6. Practicing what you preach and providing support. Iowa State University talks about four different kinds of parenting styles. The most effective style includes instilling high standards, but also good behavior modeling and lots of support and communication. What’s more, good parenting — just like being a good boyfriend — means that you should be willing to change your mind and appreciate another point of view in a relationship.

So all around, the literature shows that being a good father and being a good boyfriend — which can easily feel like full-time jobs — are not just related but contiguous. Which is great news! Once we can appreciate that they require similar skills, they can actually be totally complementary.

What Our Single Dads Taught Us

The discussion on the podcast provided great anecdotal evidence to the research. Their advice is highly personal and incredibly valuable for all single fathers. So what did we learn from our single dads?

1. Self-awareness is the skill on which all other skills are built. Dave, one of our single dads, was having a really hard time with his ex. She wasn’t respecting his time or the needs of their daughter. So how did he change things for the better? He started out with a self-assessment; He thought about why his ex’s behavior was a problem for him. He considered how he was going to talk to her so that he’d get results beneficial for everyone and not just cause a fight. “You have to get yourself in a position where you’re comfortable and confident,” he says. Knowing what to do in any given situation often comes down to knowing yourself. For Dave that meant explaining to his ex that if she was late getting their daughter that he was going to lose sleep, which would impact his performance at work, potentially costing him his job.
2. Have a good relationship with the mother of your children. When you have a child with someone, you’re almost always in a relationship with them for the rest of your life. That relationship can be financial, but it’s also parental, familial and, on some level, emotional. You don’t have to like her, but you do have to work with her. This is going to make your life easier, even if it’s hard to move into that space. What’s more, it’s going to make you look like a mature and responsible man to other women, to say nothing of the emotional benefits for your child.
3. You need to live life for yourself. Which is different from being selfish and short-changing your kids. By living your life for you — and not orbiting exclusively around your kids or even your ex — you’re setting a good example for your children. Single dad and AoC alum Tom has a 14-year-old son who was nine when he entered the program. “I had life on cruise control,” he says, recalling a period when he wasn’t really living life to the fullest. Now that he’s taken a more active role in living his own life, he’s a better role model for his son, and they enjoy a stronger relationship as a result.
4. Make time with your kids meaningful. Tom also noticed a change in how he spends time with his son. He used to do anything to avoid meaningful interactions. Now they go on adventures together rather than just vegging out in front of the television. “When he was younger I didn’t really know how to be a father.” Now he emphasizes having meaningful time with his son, which is far more enriching for the both of them.
5. Be honest about what you want in life. One thing holding Tom back in life was not being honest about what he wanted out of it. “You’re going to be angry with yourself if you’re not having your needs fulfilled,” he says — and that can include a healthy social life, a degree of independence and a support system in place. That’s going to lead to a lot of passive-aggressive behavior and anger management issues. Neither of those are a recipe for success as a father or as a man. On the other hand, being honest about what you want out of life is often the first step toward getting it.
6. Your kids will start making friends for you. Dave’s daughter isn’t the most confident girl by nature. So he used to take it upon himself to introduce her to other children her age. By doing so, however, he began to teach her confidence (yet another experience that bridges the parenting and dating worlds). Now she runs up to other children and introduces herself. In doing so, she’s helping Dave to make new friends with their parents. Adorable and inspiring.
7. Women love children. Another lesson from Dave: He spent a lot of time worrying about how to introduce the idea that he had a daughter into his dating life. Then he realized that for many women, having a daughter was an added attraction, not a problem, especially when he embraced it. “I have this adorable, smart little girl,” he says. “Who wouldn’t want to be around this?” Stop seeing your kids as a liability in your dating life and start seeing them as assets. They are a unique part of you, and they are teaching you things about life that most men simply don’t know.
8. Be willing to learn from your children. It’s a bit of a cliche, but your kids can teach you as much as you teach them. Jordan quickly noticed that kids often assimilate our material more quickly than adults because they have less baggage and emotional roadblocks. When you see your kids practicing what you preach, don’t be afraid to learn from their example. When they challenge or contradict your assumptions, take it as an opportunity to grow. Children have a wisdom parents have long forgotten — the same wisdom, by the way, that can make you unstoppable in the dating world.

All of this boils down to one thing: Not only can you be just as attractive as a father as you were when you were childless, you can be more attractive. In many ways, dads who are doing it right have a significant advantage. It might take some getting used to — it might even push you to places and attitudes you aren’t yet comfortable with — but the moment you connect these two important parts of your life, you might just find that being a great father and a great boyfriend go hand in hand. Whether you like older women or younger women, dating as a single dad is not the headache you might think it is.

For more on single dads and dating, be sure to explore our blog.

The post How to Go From Single to Sexy Dad appeared first on The Art of Charm.

A date where the two of you can’t get to know each other isn’t much of a date. On the other hand, being forced to stare at each other like you’re on a job interview can quickly get awkward.

I’m firmly of the opinion that almost anything can be a killer date. If it’s something the both of you like doing alone, there’s a good chance the two of you are going to enjoy doing together. That said, there are some things that just never make for a good first date. You can start breaking some of these out around the fourth date or so, but when you’re just getting started, here are seven bad first date ideas to definitely avoid.

What Makes a First Date Successful

Understanding what makes a great first date helps you avoid the common pitfalls. Successful first dates create the perfect balance between getting to know each other and having fun together.

The best first dates allow for natural conversation flow. You want opportunities to talk, but also comfortable silences when you’re engaged in an activity together. This removes the pressure of constant conversation.

Shared experiences create instant bonding. When you do something together, you’re building a memory that belongs to both of you. This shared foundation helps establish connection faster than just talking.

Successful dates also respect boundaries and comfort levels. First dates should feel safe and comfortable for both parties. Avoid anything too intimate, expensive, or time-consuming.

The setting should allow both people to be themselves. Choose environments where you feel confident and comfortable. Your authentic personality comes through better in familiar settings.

Good first dates end with both people wanting to see each other again. They create anticipation and interest rather than overwhelming someone with too much too soon.

Dinner Dates: Like Job Interviews For No Job

Dinner is the staple first date, but I can’t for the life of me figure out why. At some point someone decided that this is just what you do on a first date. Whoever decided that couldn’t have been more wrong, however, as this ranks among the baddest of the bad first date ideas. This ranks as just about the worst first date you can go on.

Why This Doesn’t Work: You’re forced to interact too much. It doesn’t matter how much you like each other at first. It’s too much too soon. It’s a lot like going on a job interview more than a date. If the conversation falls flat there’s nothing to do but stare at your plate and hope the awkwardness passes. Make no mistake about it, just about every dinner first date gets awkward at some point. This can turn what was white hot attraction yesterday into a great big “meh.”

Dinner dates also create financial pressure. Expensive meals suggest a level of investment that might feel overwhelming on a first meeting. The formal setting can make people feel like they need to be “on” the entire time.

Table placement forces direct eye contact for extended periods. While eye contact is important, too much creates intensity that many people find uncomfortable during initial meetings.

Food choices become a source of anxiety. People worry about ordering something messy, expensive, or unusual. These concerns distract from getting to know each other.

What to Do Instead: Just about anything. But if you’re both really into food a great alternative to the dinner date is to go somewhere way more casual like a hole-in-the-wall stand-up place or to cook food together. It allows the two of you to communicate, but also offers a task to concentrate on. What’s more, shared tasks create rapport between people. But only do this if you’re both comfortable being at someone’s house. It’s less awkward than dinner, but far more intimate.

Food trucks and casual outdoor markets work perfectly. You can walk around, try different foods, and share small plates. The movement and variety keep things interesting and low-pressure.

Cooking classes provide structured environments for food lovers. You learn together, laugh at mistakes, and create something to enjoy afterward. The instruction and activity remove conversation pressure.

Farmers markets offer great alternatives for food enthusiasts. You can sample products, discuss preferences, and grab casual bites while walking around. The environment feels relaxed and unpretentious.

Movies: The Best Way to Learn Nothing About Your Date

Going to see a movie on a first date is on the opposite end of the spectrum from the dinner date. If a dinner date gets you too up close and personal, a movie can actually drive you further apart. It’s just as bad of a misstep on the first date.

Why This Doesn’t Work: You’re not going to get any chance to get to know one another, which is what a first date is all about. You’re going to sit in silence the whole time. Even if you have other parts of the date planned you’re going to kill the momentum by sitting in a dark room with her for two hours. This is more something you do with a girl that you’re dating on the regular rather than something you do with a girl on the first date.

Movies create artificial shared experiences. You’re both watching the same thing, but you’re not creating memories together. The experience belongs to the filmmakers, not to your relationship.

Dark theaters discourage interaction and observation. You can’t read body language, facial expressions, or other important social cues. These elements help gauge interest and comfort levels.

Movie choices can become contentious. Different tastes in entertainment might create immediate compatibility concerns. Horror movies might be too intense, comedies might not land, and dramas could set the wrong mood.

The time commitment is significant without payoff. Two hours is a substantial investment for an activity that doesn’t advance your connection with each other.

What To Do Instead: Much like dinner, the answer here is just about anything except dinner, obviously. But what can movie lovers do instead? You might try and see if there’s a famous shooting location near you or if there’s a movie star’s grave within driving distance. But that type of excursion might not be enough to carry a first date. So I’d advise you to find something else the two of you like that facilitates conversation about film while you do something else.

Drive-in theaters offer a better movie experience for dates. You can talk during the film, enjoy snacks you bring, and maintain a more relaxed atmosphere. The novelty factor makes it memorable.

Film festivals and special screenings provide more interactive experiences. These events often include discussions, Q&A sessions, or social components that encourage mingling and conversation.

Outdoor movie screenings in parks create casual, picnic-like atmospheres. You can arrive early, chat during setup, and discuss the film afterward while walking to your cars.

Movie trivia nights at bars combine entertainment with interaction. You work together as a team, celebrate correct answers, and learn about each other’s movie knowledge.

Family Stuff Takes It Way Too Seriously

It might sound strange, but I hear about guys doing this. Mom prepares dinner or you swing by at a big family gathering or tote your first date along to some kind of family function. I mean, I’ve heard guys talk about bringing a first date to their sister’s wedding. Talk about your bad first date ideas!

Why This Doesn’t Work: Too much, too soon. Think about it: How would you feel if a girl asked you to get together some time and told you that you’d be meeting her father. It would throw you off. It would make things awkward. It would put you on the defensive. What’s more, you’d have every reason to feel like things were a little bit off. You’d probably wonder why there wasn’t someone else available.

Family introductions carry heavy implications about relationship seriousness. Most people aren’t ready for that level of commitment after just meeting someone. It suggests expectations that haven’t been established.

Family dynamics can be overwhelming for outsiders. Inside jokes, family tensions, and complicated relationships create confusion for someone trying to make a good impression.

Your date becomes a performer rather than a person. She’ll feel pressure to impress your family instead of focusing on getting to know you. This creates artificial behavior and stress.

Family members might inadvertently embarrass you or share information you’d prefer to reveal yourself. Baby photos and childhood stories should come later in relationships.

What To Do Instead: As a general rule, it’s good to just have it be you and her on a first date. You want to show her that you’re interested in having some one on one time with her and you want to do it in a way that’s appropriate for two people just getting to know one another. Skip the family function and ask her out some weekend when you’re completely free.

Plan activities that showcase your independence and decision-making skills. Choose restaurants, activities, or locations that reflect your personal interests and taste.

Save family introductions for when you’re both ready to take things to the next level. This usually happens after several successful dates and mutual interest is established.

Group Activities With Your Friends: The High-Pressure Date

I am totally a huge proponent of group activities. In fact, I throw a pool party once a month where I invite all kinds of people. It’s a great time, but it’s not a first date.

Why This Doesn’t Work: It’s really not that much different from introducing her to your family on a first date. After all, friends are basically the family that you choose. If a dinner date can feel like a job interview, a group activity with your friends as a first date can be like a performance review. At the end of the day, it doesn’t matter how cool and open your friends are. She’s going to feel like they’re judging her; And let’s be honest they probably are.

Group dynamics can make it difficult for your date to show her personality. She might feel like she needs to perform for the group rather than be herself.

Your friends might monopolize your attention, leaving your date feeling ignored or like a third wheel. Friend groups often have established conversation patterns that exclude outsiders.

Inside jokes and shared history can make your date feel left out. References to past events or people she doesn’t know create barriers to inclusion.

Your date might worry about how your friends perceive her, adding unnecessary pressure to an already nerve-wracking situation.

What To Do Instead: There’s plenty of time for you to meet her friends. A date is about the two of you connecting with one another. Much like your family, you want to take her somewhere so that you two can spend time together. A good alternative to this for guys who are nervous about one on one? Hit up an art gallery, or something that allows the two of you to physically separate a bit on the date. Then, if you’re feeling up to it afterward, ask her to join you for a drink somewhere.

Choose activities that naturally include breaks from intense conversation. Art galleries, museums, and markets allow you to walk around and focus on external things when needed.

Group activities work better as second or third dates when you’ve already established basic compatibility and comfort with each other.

Your House Is Phoning It In

Obviously, this is something every guy has done at least once a first date. Rather than making it a date, he asked her to “come over” to “hang out.” But that’s not a good first date once you get out of high school.

Why This Doesn’t Work: “Come over and hang out” is basically you saying to her that you’re not interested enough in her to think of something fun for the two of you to do together. It’s showing the least amount of interest possible in a girl. It also signals a certain expectation early on. It doesn’t matter if you don’t see it that way. It’s how she’s going to see it and she’s not going to be a fan.

Home dates create inappropriate intimacy levels for first meetings. Private settings suggest physical expectations that many people aren’t comfortable with initially.

Your living space reveals personal information you might not be ready to share. Messy rooms, questionable decorating choices, or personal items can create wrong impressions.

Home environments limit escape options for both parties. If the date isn’t going well, it’s harder to end gracefully when you’re at someone’s house.

The casual nature doesn’t demonstrate effort or investment in getting to know her. It suggests you’re not willing to put thought into creating a special experience.

What To Do Instead: A walk in the park costs the same as hanging out at your house, and it can still be a great experience. It also provides way more opportunity to get to know one another without stressing out your date too much. In fact, walking side by side is often way more conducive to conversation than staring at one another.

Coffee shops provide comfortable, public alternatives to home dates. They’re casual enough to feel relaxed but public enough to maintain appropriate boundaries.

Outdoor activities like hiking or walking tours combine exercise with conversation. The movement makes people feel more relaxed and natural.

Save home dates for later in the relationship when both parties feel comfortable with increased intimacy and privacy.

The Mall Makes You Into a Walking Wallet

Believe it or not, I’ve talked to more guys than I care to recall who took girls on a first date to the mall. They usually end up spending a ton of money on her and basically being her shopping rack for the evening.

Why This Doesn’t Work: Pretty obvious, right? The mall just isn’t an inspiring locale for your first hang-out. Malls are sterile, busy, impersonal. They’re designed to accommodate most people, rather than creating unique experiences for her.

Shopping centers encourage consumer behavior rather than meaningful interaction. The focus becomes acquiring things rather than getting to know each other.

Malls create financial pressure and awkward gift-giving situations. You might feel obligated to buy things, or she might expect you to pay for purchases.

The environment is often crowded and noisy, making intimate conversation difficult. Food courts and common areas don’t provide romantic or memorable settings.

Mall dates lack originality and thoughtfulness. They suggest you haven’t put effort into planning something special or unique for your time together.

What To Do Instead: You might be surprised to hear that the shopping date isn’t always a bad thing. Hitting up a cool used bookstore, for instance, can be a killer first date, especially if the two of you are introverted and bookish. Tell her to go find a book she loved from her childhood, a book she loved in high school and a book she loves today. You do the same. You’re going to find out a ton about each other just from this simple exercise. Lots of bookstores now double as restaurants or cafes, which makes it a fun option in most cities.

Vintage stores and thrift shops provide more interesting shopping experiences. You can laugh at unusual finds, try on silly outfits, and discover unique treasures together.

Local markets and artisan fairs showcase community creativity. These venues support local businesses while providing conversation starters about art, crafts, and local culture.

Record stores appeal to music lovers and offer natural conversation topics about favorite artists, concerts, and musical memories.

Open Mic Night: Save Your Performances for Later

Why This Doesn’t Work: Cringe. Double cringe if you’re the one performing. Most acts at open mic nights are not great. If you’re the one performing, wait for her to ask you to come check out your act some time.

Open mic performances create awkward situations where you’re both hostage to amateur entertainment. Bad performances make everyone uncomfortable, including your date.

If you’re performing, your date becomes your audience rather than your companion. The focus shifts to your performance instead of getting to know each other.

Performance anxiety can ruin the evening if you’re worried about how you’ll do on stage. First date nerves and performance nerves don’t mix well.

Even if you perform well, the attention and adrenaline can overshadow the intimate getting-to-know-you aspect of dating.

What To Do Instead: Take her to a real performance by a professional. This can be tricky. On the one hand, most concerts and performances don’t allow for a lot of interaction and time to get to know one another. Still, if the two of you head out to a bar where there’s some kind of performance going on, you can hang in the back and get to know each other in between acts or even in between songs or routines. Make sure you two are having your moment within the larger event.

Comedy clubs provide professional entertainment with natural conversation breaks between sets. Shared laughter creates positive bonding experiences.

Jazz bars and intimate music venues allow for conversation during and between performances. The sophisticated atmosphere creates romantic settings.

Local theater productions offer cultural experiences that provide discussion topics for before, during intermission, and after the show.

Additional First Date Mistakes to Avoid

Beyond the seven classic mistakes, several other first date choices consistently create problems for new couples.

Sporting events seem fun but often fail as first dates. The noise level makes conversation difficult, and strong emotional reactions to games can overshadow getting to know each other.

Expensive activities create financial pressure and set unrealistic expectations for future dates. Skip the helicopter rides and five-star restaurants until you know you’re compatible.

Nightclubs and loud bars prevent meaningful conversation. Dancing can be fun, but not when you’re trying to establish basic communication and compatibility.

Adventure activities like skydiving or bungee jumping might seem exciting, but they’re too intense for first meetings. Save extreme activities for when you know each other better.

Wine tasting and brewery tours focus too heavily on alcohol consumption. These activities work better when you’re comfortable with each other’s drinking habits and limits.

Escape rooms and puzzle-solving activities can create stress and conflict. While problem-solving together can bond couples, it can also reveal incompatibilities too early.

Long road trips or day-long activities trap both parties in potentially uncomfortable situations. Keep first dates to reasonable time commitments that allow graceful exits.

Proven First Date Ideas That Actually Work

Understanding what to avoid is only half the battle. Knowing what actually works helps you plan successful first dates that create genuine connections.

Coffee dates remain popular because they work. They’re low-pressure, time-flexible, and allow for easy conversation. Choose interesting coffee shops with character rather than generic chains.

Walking dates provide natural conversation flow while exploring neighborhoods, parks, or downtown areas. The side-by-side positioning feels less intense than face-to-face conversations.

Museum and gallery visits offer built-in conversation starters and natural movement patterns. You can discuss exhibits, share reactions, and learn about each other’s interests.

Farmers markets combine multiple activities in one location. You can sample foods, look at crafts, listen to live music, and grab casual bites together.

Mini golf and bowling provide light competition and shared activities without requiring serious athletic skills. These environments encourage playfulness and laughter.

Cooking classes teach new skills while creating shared experiences. Working together toward a common goal builds rapport quickly.

Outdoor festivals and street fairs offer variety, entertainment, and natural conversation opportunities. The carnival-like atmosphere creates positive, fun memories.

Bookstore browsing appeals to intellectual types and provides insight into each other’s interests, values, and personality through book choices.

Reading the Signs During Your Date

Successful first dates require awareness of your date’s comfort level and interest throughout the experience. Learning to read these signs helps you adjust accordingly.

Positive body language includes leaning in during conversation, making regular eye contact, and mirroring your movements. Genuine smiles and laughter indicate comfort and enjoyment.

Active participation in conversations and activities shows engagement. When someone asks questions, shares stories, and contributes ideas, they’re investing in the interaction.

Physical proximity provides important clues. Someone who maintains comfortable distance without constantly moving away is feeling at ease with your presence.

Time awareness can indicate interest levels. People who check their phones frequently or mention time constraints might not be enjoying themselves fully.

Negative signals include crossed arms, minimal eye contact, short answers, and frequent mentions of other commitments. These behaviors suggest discomfort or disinterest.

Pay attention to energy levels throughout the date. Initial nervousness is normal, but persistent anxiety or discomfort indicates the activity or chemistry isn’t working.

Listen for enthusiasm in their voice when discussing topics or suggesting activities. Genuine excitement about shared interests predicts compatibility better than polite agreement.

How to End a First Date Properly

The conclusion of your first date sets the stage for potential future interactions. Ending gracefully requires reading the situation and responding appropriately.

Keep endings simple and pressure-free. Thank them for their time, express that you enjoyed getting to know them, and suggest future contact if the date went well.

Avoid immediate declarations of love or intense future planning. First dates should end with positive feelings and anticipation rather than overwhelming emotions.

Physical contact should match the comfort level established during the date. A hug might be appropriate if you’ve had good chemistry, while a handshake works for more reserved interactions.

Follow up within a reasonable timeframe, typically within 24-48 hours. Express gratitude for the time spent together and gauge interest in future meetings.

Be honest about your level of interest rather than leading someone on or completely cutting contact without explanation. Clear communication prevents confusion and hurt feelings.

If you’re not interested in continuing, express appreciation for their time while making it clear you don’t see a romantic future. Be kind but direct.

When you are interested, suggest specific next steps rather than vague promises to “get together soon.” Concrete plans demonstrate genuine interest and initiative.

Frequently Asked Questions

How long should a first date last?

First dates should typically last 1-3 hours. This provides enough time to get to know each other without creating pressure or fatigue. Coffee dates might be shorter, while activity dates could run longer naturally.

Who should pay on the first date?

The person who initiated the date traditionally pays, but many couples prefer to split costs. Discuss this beforehand or prepare to handle it gracefully based on the situation and your date’s preferences.

What should I wear on a first date?

Dress appropriately for the planned activity while looking polished and put-together. When in doubt, business casual works for most first date scenarios. Your appearance should show you care about making a good impression.

Is it okay to kiss on the first date?

Physical contact depends entirely on the chemistry and comfort level established during the date. Read body language and verbal cues carefully. When in doubt, err on the side of caution and save more intimate contact for future dates.

Read next: The 13 Tests People Run on You

Like I said: A good first date can be just about anything. But there are some places and situations that just make for bad first date ideas. What first dates have you gone on that have been a total bust? I’m curious to know what other places men have gone to that just didn’t seem to work out for them. Leave a comment and let us know.

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• 7 Signs a Girl is Attracted to You

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