Guys often ask me what to say to girls. I get it — it can be really hard to know how to break the ice and start a conversation. And once you do get a conversation started, it can be difficult to keep the conversation moving forward. Which is why having some solid, standard questions handy can make it much easier to build and deepen a connection.
But having prepared questions raises another issue. Too many guys ask girls questions that are either too boring (“Come here often?”), too personal (“Where do you live?”), too silly (“If you could be a flavor of Kool-Aid, what flavor would you be?”) or too much like a job interview (“What do you want to be doing in five years?”). What you need aren’t just questions, but good questions.
More than that, you need to know what makes a question good, so you can come up with your own questions spontaneously, effectively, at the moment. Questions that give you meaningful information, show genuine interest and allow you to be authentic and open. Questions that will get her interested in you, while allowing you to decide if you are interested in her. Questions that avoid the conversational boxes that turn a fun opportunity into a dull exchange.
So here are ten questions that accomplish everything a good question should. But because we’re not just here to give you memorized questions to pull out of your back pocket, I want to talk about something important first: what makes these good questions in the first place.
What makes a question good?
There’s nothing wrong with having two or three fall-back questions to use as training wheels when you’re starting out. But you don’t want her to feel like you’re just firing a bunch of canned interview questions at her, because that usually creates an inauthentic, stressful exchange. What you really want is the ability to come up with your own meaningful questions and weave them into the conversation organically. So how do you ask good questions?
Good questions have some basic characteristics.
- Most importantly, good questions express genuine interest. Don’t ask if you don’t care.
- Good questions are open-ended. They allow for in-depth answers. This is how you actually start learning things about her. One-word answers don’t tell you much and basically any question can be worded to elicit a longer answer.
- A good question allows for some back and forth. After she answers, you can give your own answer, because if you two are really getting into each other, she’s going to be just as interested in your answer as you were in hers. Ideally, a question should lead to more questions after she’s done answering.
- When you ask a good question, it’s easy to go down a side alley and a detour or three. That’s fine! When you ask a question, you want to know her answer, but it’s more important to keep the conversational ball rolling and keep her interested. So if she starts talking about the answer to your question and dips into some unrelated tangents, that’s a great sign. Roll with it and enjoy.
- It sounds obvious, but it’s still worth mentioning: A good question fits with the rest of the conversation. If she’s talking about her job, asking her about her car isn’t a great fit, though asking her about her education makes sense.
- Good questions get people talking about subjects they’re interested in on a positive note. Fewer things will get a person to like you more and faster than asking them to talk about something they’re already interested in.
- Finally, a good question helps to lead you both toward real conversation, not just taking turns asking questions. Good questions are bricks in a road from not knowing someone at all to getting to know them quite well.
The questions below are great examples to start, but they’re just that — examples. Rather than trying to memorize them, ask yourself why they’re good questions, and how you might be able to adapt them in specific conversations. It’s best to use them in an appropriate, organic way, but if you find the conversation dwindling and you want to keep it going, don’t be afraid to pull one out. At the end of the day, you’ll want to come up with questions that flow naturally, and let the conversation direct itself.
“What was the best part of your week?”
Think of this question as one potential replacement for the dreadful “So what do you do for a living?” You might be legitimately interested in what she does for a living, but there are a few problems with that question. First, it’s boring — every other guy has asked her that before. And because everyone has asked, she’s tired of answering. Asking what someone does is also closed-ended. Once she gives you a one-sentence answer, there’s not much more to say. And finally, she probably doesn’t want to talk about work.
Compare that with “what was the best part of your week?” In this formulation, you allow her to give you the information she’s most interested in providing. That might be about work, but it could be about school, yoga or the fun projects she has going on the side. Whatever her response, she gets to determine what she wants to share with you about her week — and you get to listen. Now you’re focused on fun, positive experiences, and the conversation will perpetuate itself. As a result, she’ll associate the elevated mood she experiences with talking to you. And that’s how organic conversations work.
You’re also getting a small window into her overall life by asking her what the best part of her week is. You’ll learn a lot from what she chooses to tell you about. She’s not giving you a laundry list of everything she did this week. She’s telling what she’s most excited about. That’s excellent information for you to decide whether this is someone you’d like to spend more time with.
“What’s the worst part about dating?”
This one breaks our rule about being positive, but for a great reason. You’re not trying to get her to “vent” or even picking her brain for information about what not to do (though you will get useful information about that too!), but rather to lightheartedly acknowledge that dating can be awkward, stressful and unpleasant at times. You want to smile big and make sure she takes this an invitation for lighthearted banter. If she’s open to it, this can be a great foray into hilarious stories you two can share about the funny process of dating.
Something deeper will also happen here. Opening up your vulnerabilities is a great way to bond. When you each expose parts of yourself that are a little uncomfortable, you’re showing a part of yourselves that most people don’t get to see. Not only can you learn more about each other this way, but you can also begin establishing comfort and expressing interest. After all, who shares vulnerability with people they don’t like?
“Who are you closest to in your family?”
Think of this question as a targeted way of asking where she grew up and what her childhood was like. Because this question is closed and targeted, you’ll want to follow up with something like “How did you two become so close?” This question might provide a short answer, but it directs the conversation to a place where you can start asking a lot of follow-ups.
The key here is to recap what she said (“It sounds like you and your dad spent a lot of time golfing together”) and then ask a relevant question that also pivots the conversation a bit (“What about your mom? What did you two do together?”) In fact, you might choose this question specifically as an exercise so that you get better at thinking on your feet in the middle of a conversation and asking solid follow-up questions.
“What’s the thing you most want to do with your life?”
Yes, this is a question about her bucket list, which can be rote and sometimes intimidating. Still, it’s one of those questions everyone wishes someone would ask, but no one ever does. The key is to ask it in a genuinely curious, nonjudgmental way.
Make sure she knows that you don’t necessarily mean something “big” like “conquer Mars” or “have 16 kids.” It could be something as simple as seeing the Grand Canyon, or an act of commonplace thrill-seeking like jumping out of an airplane. If her answer is kind of “boring” (say, work-related), clarify it by giving your answer. Just commit to your answer, use it as an example and let her talk.
“What do you like about where you work?”
Sure, this question can be a jazzed-up alternative to asking what she does for a living. But in the process, you’ll find out more than just where she works. If she like her job, you’ll find out what she’s most passionate about. If she doesn’t like her job, you’ll learn what it is about it that keeps her going back every day.
You can explore a person’s values and priorities by asking them what they like about where they work. You can then use this question to pivot to more specific questions about their passions, interest, and aspirations. There’s a lot of follow up woven into this question. You can ask 20 questions about her job from here, or none at all.
“What was cool about where you grew up?”
Very few people ask this question, but when you think about it, it’s a great way to get to know someone. Especially if you live in a city like LA, New York or Portland with a lot of transplants, you’re giving someone the opportunity to remember who they were before they got here. And not just to remember who they were, but what they like best about the place they came from.
Even if someone has an overall negative impression of where they came from, this question keeps things positive. What’s more, if they do have a negative impression of where they grew up, there’s a good chance no one has given them the simple gift of being allowed to reminisce about what was positive. And you’ll discover a ton of interesting personal detail in the process.
“How did you decide on your major?”
A variation on the “What do you like about your job?” question, this question gets more at someone’s hopes and dreams. Think about it: Choosing a college major is, for a lot of people, one of the only big decisions they make on the basis of passion. Even majors like pre-med and law tell you more about a person’s dreams than what they think is “realistic.”
And that’s a cool side of someone to see. While we all certainly need to be grounded in reality, it’s also nice to venture outside of that bubble. When talking to someone about their major and how they arrived at it, you’re offering them the chance to reconnect with the topics, themes, and challenges they love — that part of their life when they didn’t make all their decisions based on what’s “realistic.”
“How did you two become friends?”
When you approach groups of women or even mixed groups, it’s smart to involve everyone in the conversation. Because you are interjecting, it’s your responsibility — and part of the fun! — to engage every person in the immediate group, even if your focus is on one person in particular. Asking how these people became friends is an excellent place to start.
In addition to ingratiating yourself with their circle, you’ll also learn a great deal about their past. As they talk, listen carefully for revelations of their interests and priorities. You can avoid becoming a mere audience for their life story by using their response to create new, organic questions, and building a conversation from there.
“What’s the coolest thing in this city no one knows about?”
One thing that people in cities pride themselves on is knowing about locations, events and other local happenings. When you ask her this question, you’re giving her the opportunity to show off a little bit. You’re also potentially letting her do the work in terms of coming up with a first date idea.
There’s a minor “tell” nested in this question. When she talks about a secret spot, you’ll know she’s interested when she wants you to go there too. Hidden attractions are jealously guarded, so if she wants to take you there, things are going well.
“What the coolest place you’ve ever traveled to?”
Even people who don’t travel a lot like to talk about travel. So if you ask her and she says “I haven’t really been anywhere” you can just ask her where she most wants to go. Asking about travel allows you learn both about where she’s been and where she wants to go. The places people have traveled as well as the places they want to travel in the future gives you a lot of insight into who she is.
After she answers, follow up by asking her what she liked about it and what she did there. A trip backpacking around Europe, a year spent in the Peace Corps and a semester studying abroad in Taiwan are all very different kinds of trips, giving you very different insights into who the person is. If you have cool travel experiences, you can share them. Or maybe she’s been someplace you’d like to go and you ask her about it. Either way, it’s a great way to bond over past experiences and shared aspirations.
As I mentioned earlier, it’s important for you to come up with your own situationally appropriate variations on these questions. For example, “What was cool about where you grew up?” can sound a little stiff in comparison to something like “I’ve heard Portland is really cool. What did you like most about growing up there?” Don’t worry about memorizing these questions. They’re just general themes to explore.
If you find any of these questions particularly interesting, trot them out as much as you want. And, as always, we’re interested in your feedback. What questions do you like to ask girls you’ve just met? What works, what doesn’t, and why?
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