Why Hitting a Home Run Isn't Always Your Best Move

Why Hitting a Home Run Isn’t Always Your Best Move

Three strikes and you’re out. Keep waiting for the perfect pitch to hit a home run every time and you might win a few cheers, but you won’t win the game. Here’s how to play at your best. [Photo by CNU Sports]

When the ball comes over home plate, a man’s first reaction is to try and hit it out of the park.

If we keep waiting for the perfect pitch to hit the ball out of the park every time, we might win a few cheers, but we won’t win the game. Even the 1927 New York Yankees team led by Babe Ruth and Lou Gehrig never won a game by hitting every ball over the fence. In fact, the standing record for any player hitting four or more home runs in a single game was when Bobby Lowe did it in 1894, more than 120 years ago. Connecting with new people is kind of like that.

As men, we want every first conversation to go smoothly. It’s jarred into our memory that nothing counts as much as that first impression. When we first meet someone, whether it’s a potential client or the cute girl at the bar, we spend more time trying to think of a witty opening line than we do actually speaking to them. Is it a matter of building up confidence, or is it ingrained fear that if we can’t make the intro memorable, they’ll forget about us entirely?

So imagine a game of baseball. The park is full of fans cheering, and you’re called up to the plate. It feels like every eye in the room is watching you, critiquing your every move. Sound familiar?

You get up to the plate, kick the dirt from under your cleats, and bear down waiting for the perfect pitch. The first pitch comes barreling in, and it’s a little high and just a bit outside. You could have hit it, and it probably would have got you on base, but certainly not around the diamond for a standing ovation.

Meeting people for the first time is a lot like this. You walk up to them. You open and say hi, maybe ask them a question, but their pitch — or answer — isn’t everything you hoped for. They weren’t telling you to get lost, but they weren’t tossing their head back in laughter and asking you for your number or email. You could have swung at the pitch, and likely kept talking to them for at least a little bit more time. Instead, you have this grand idea of how great it would be to hit one out of the park. Say something so witty and fantastic that it seals the deal on the spot and you walk away with the potential client’s blank check, or the cute girl’s number and her asking you out on that first date.

These out of the park, over the fence, World Series kind of lines happen once in a while, sure. But if we only relied on these lines to move a conversation forward, we would end up striking out far more often than we made it to first base.

So, that second pitch. It comes barreling in. You had the courage to follow up that first pitch with another question. If it’s the girl you’re interested in, maybe this one is “what do you do for a living?” and she comes back at you with her pitch, “I’m a nurse.”

Well you don’t have a home run response to that. So since it’s not right down the middle, you decide not to swing. But this is only her second pitch, and you’re not out yet. You’re not a quitter, but you’re feeling the pressure. So you pop out another question. “Do you like being a nurse?”

At this point, you’re so focused on your last chance to hit a homer that you spit out a question she’s likely going to view as ridiculous. I mean, what nurse doesn’t enjoy their job?

So she says, “Yeah, I love it,” and the conversation falls flat. Her pitch comes back at you, and there’s still a chance to get on base. But you’re so focused on splitting that ball open in front of the crowd, that even though it’s still in the box, you let it slide by. And guess what? That’s strike three. You’re out of there, buddy. So even though there was still a chance to save the game, you probably just shrugged, looked at your feet, and said: “Oh, that’s cool.”

And now, she looks at you, realizes you just wasted five minutes of her time, and even though she probably thought you were cute and may have even just told her friends she wants to meet someone and get back in the dating game, you fucked it up and the conversation is dead because she can’t figure out how to save it either. So she says, “Well, I should get back to my friends,” shakes your hand, and says, “Nice meeting you.” Then you slink off the home plate, letting the next guy in line step up to bat.

So what could you have done differently? Any baseball coach is going to tell you that your focus should never be hitting the ball out of the park. Just get on base. Even if you have to take a ball to the shoulder, get on base. Because once you’re on base, you at least stand the chance of getting to all the bases before running home for the win. Strike out, and there’s not a chance in hell.

Rather than coming to the conversation with a script of lines that sound like they’re from the last rom-com you saw — where you have to wait for the perfect opening or opportunity to use it — just say hi.

Focus on open-ended questions, not ones where they can answer in one word. Remember, whether it’s the girl you want to ask out or the prospective client you want to pay for your kid’s college education at Harvard, people love to talk about themselves. And if you can get them talking to you, a stranger, well, then you’re not really a stranger anymore, are you? And the longer you can keep them talking, the better chance you have of getting on base.

“So what do you do for a living?”

“I’m a nurse,” she says.

“That’s awesome; it must be a pretty exciting job. Tell me, what’s the best part of your day?”

“It is pretty exciting. I love getting to know my patients and of course, it’s pretty cool being able to save lives.”

“So you’re basically telling me I’m talking to a real-life superhero. That’s phenomenal. I have to ask: what’s your favorite story of saving a life?”

Well, you’ve got her attention. By now, you’re on base and she’s as interested and engaged in the conversation as you are. She’ll tell you stories, and you can suggest you grab a drink. If you keep the momentum going — but let her talk — you’re likely going to leave with her telling you she wishes she could just stay and hang out with you all night. Well, get her number. Ask her out, and I guarantee that at this point, you’re going to get a yes. You’re not going to be cut from the team; you’ll see her at the next game, and you’ll have another three chances to win her heart again.

How Can You Ensure You’re Playing at Your Best Each and Every Day?

1. Listen

Don’t queue up questions. In fact, don’t even think about it. Because if you’re trying to think of the wittiest comment you can come up with while they’re talking, there isn’t any hope you were listening and heard what they said. Instead, focus on who you’re talking with. Watch their lips and body language and take in everything they say. Then use that information to extract more. If they say they like coffee, don’t ask, “Do you like dark roast?” because that’s likely only going to get you a one-word answer of “yes” or “no.” If the future client mentions his kid loves baseball, tell him you have tickets and buy his kid some tickets to a game. Send them to his office next week with a note and business card. Not only will it show him you’re serious about earning his business, but that you pay attention and are man of your word.

2. Ask Open-Ended Questions

So if coffee becomes part of the conversation, ask, “What are your thoughts on that new coffee shop that just opened on _____________?” If she says she hasn’t been, don’t go for the home run and ask to take her. Tell her why it’s worth going and then see where it goes from there. At the first meeting, your only goal should be to have a great conversation and walk away with a number. And if you can keep her engaged and talking, you will get that number, and she will remember you when you call. Try to offer a question and respond with statements that are emotional or show your feelings on the matter as well. This way, she feels like it’s a conversation that’s going both ways, and it won’t come across as forced.

Asking yes or no questions limits that conversation. It stops it short — just like getting the wind knocked out of you. Most men will immediately revert to asking another question, and another, and another. Soon, it’s not a conversation. It’s an interview. No one likes being interviewed.

3. Take Skill-Building Workshops

Join an improv class. We highly recommend it, and in fact, if you come out for our bootcamp, you’ll end up doing a ton of improv and see just how effective it can be. Most major cities have a theater school that offers improv classes for adults. A quick Google search should net you a few options. Not only is it a great place to learn how to keep momentum in a conversation going, but it can also be a great place to meet new people. If you’re the type of guy who has difficulty with first introductions, there is no class better suited to help you connect with the ball, and get on base every single time.

Social meetups are another fantastic option for men to meet people in an environment where meeting new people is the goal. We’re not talking speed dating here. We’re talking groups of like-minded locals who meet up at a bar, a coffee shop or even a park to get together and meet people. theCHIVE hosts meetups in most cities, and for many, it’s not just a social gathering, but an opportunity to meet potential dates. Just be aware of the type of meetup you’re attending and make sure it’s in your comfort zone. Meetups like the ones held by theCHIVE are often very sexually charged and ones in the summer will likely be pool parties or other parties where the attire is no different. If you’re in your forties, this may not be the best meetup for you. Meetup.com is another place to find groups of people from all ages and walks of life who bond over common interests.

If you’re after business connections, join a golf club, tennis club, business meetup, etc. Use your newfound skills to acquire leads in an environment that is well suited to meeting new contacts and enhancing your rolodex.


Whether you’re meeting a potential date, or it’s the first interview with a new client, being able to have a meaningful conversation is a life skill. It may win you a date; it might get you a promotion, or it may just mean signing that new client you were fighting for. The opportunities are endless when you can connect with someone capable of having an impact on your life for the better. Don’t play as if every result has to be a home run when there are better ways to win the game.