Why Teenage Boys Should Be Courageous and Ask the Girl Out!

Guys, I want to encourage you to do something that some of you might find daunting. Maybe even scary. I’m talking about approaching a girl that you know and asking her out. You’re not asking her to get into a relationship; you’re not asking her to be your girlfriend; you’re just asking her if she’d want to get dinner at that new pizza place she was talking about.

Most of you don’t admit it to girls, but in my research with thousands of young people over the years I’ve heard most guys have a “stomach in knots” feeling at the idea of asking that question. Some of you have already done that, others haven’t, but regardless, it can feel as if you are totally laying yourself on the line. And who wants to risk rejection? What if she says “Um, no thanks?” Worse, what if she laughs about it with her friends, and you end up feeling like a fool?

Those thoughts can make any reasonably sane male mortal decide that he can get around to officially asking a girl out a few years from now. Like, when he’s 30.

So if you’ve been hesitating, why am I suggesting that you do this? There’s a very important reason, which comes not just from me but from the thousands of girls I’ve interviewed.

Many girls appreciate when a guy asks her out rather than the other way around  

Girls may look sure of themselves as if it doesn’t matter to them who makes the first move. But you need to know that, inside, most girls are deeply hoping a guy will be the one to reach out—even though it might not actually seem that way with the girls you know.

The girls you know may seem way too confident for that. They’re the ones who are constantly talking about match-ups: “So … do you like so-and-so?” They’re the ones who are texting you after school. If you don’t make the first move, they might.

I said that (“If you don’t make the first move, she might”) when I was speaking at a youth event not long ago and the guys’ reaction was hilarious: “Suweeet!” “And why is that a problem?!” It was clear they were all thinking, Why would I want to risk making the first move if she will just do it for me?

Here’s why. What most girls really want is a guy who is confident enough to approach them. Now, there’s no reason why a girl can’t be the one to take that first step, if she is interested and if that is authentic to her. But when you take that first step instead, it demonstrates a quality girls really admire—self-confidence. When we were researching our book For Young Men Only: A Guy’s Guide to the Alien Gender, we surveyed girls to ask them what traits they find most attractive in a guy. Self-confidence (without being cocky) was one of the top three.

Why does stepping out in self-confidence even matter? Two reasons.

Most girls have a secret vulnerability—and you asking her out can be very affirming

I know it doesn’t look like it, but even the most amazing girl likely has a secret vulnerability: she wonders if she is worth something. If she is worthy of being loved. If she is special in any way.

On our nationally-representative survey for For Young Men Only, 91% of girls felt that way. Let me make that very real to you. This means that in any classroom or any friend group, if there are 15 girls in the room, that means only one or two of them do not feel that way. The other 13 or 14 wonder things like, “Am I the type of person who anyone will ever love?”

Think about that for a second. Think about a particular female friend, who you think is beautiful and a great person. If she is like most girls, she truly wonders if she is the type of person who anyone will ever love.

So when you take that step of courage to tell your friend Brianna, “You have mentioned wanting to see that movie a couple of times. Want to come with me on Saturday?” It is unbelievably affirming to her. It says to her, “You are special. You are the type of person who someone will love someday.”

It doesn’t mean that you will be that boy—just that she is that type of girl. It is an action of not only affirmation but genuine kindness.

You approaching her builds a habit of courage—instead of a habit of passivity

One of the things I hear often from women in hurting marriages is despair, pain or anger about the fact that their husband has checked out, become passive, backed off. This is not the place to get into all the reasons why, but it is clear that this is one of the temptations of guys these days. And it happens among high schoolers too. You may have noticed that if you just wait, girls will text you about going out or about joining the group for coffee. You may have noticed that if you are slow in leading the class presentation, someone else will take it over and do more of the work. It can become a dangerous temptation.

Now, that may not be you at all. But some guys tell me that they are subconsciously thinking, If I just wait, someone else will do it for me and I won’t risk doing it wrong / being rejected / feeling stupid. It sure is easier.

But giving in to that temptation means building a habit of being passive. Sitting back and seeing whether someone else will take action instead. To build yourself as a person and as a leader, it is so crucial instead to take steps of courage—like approaching that girl you like (in person rather than over text!) and asking her to do something over the weekend.

Now is your chance to practice—and build confidence.

Guys, this is your opportunity to practice. I know it’s scary. But if you don’t practice, it’s only going to make you more nervous. The more you think about anything that’s difficult to do, the larger it looms in your mind, right? And the more you delay and overthink it, that challenging thing can take on proportions so big that it starts to seem impossible.

But the good news is that once you take that step, you’ll get more accomplished at it. It is almost like putting in the work to build muscles. It can take work, can sometimes be painful, and can take time before you see results—but in the end you’re glad you’ve done it.

Yes, you could get turned down. Be okay with that. And if it happens, resolve in advance to learn from it (maybe ask an older, wiser guy what you could have done differently, if anything), and try again. Focus on the successes rather than the failures. And as you build the confidence needed to ask a girl out by actually doing it, you develop one of the qualities that women find most attractive.

So guys, here’s the challenge for you: take the step. Think of a girl that you like, that you admire, that you are probably already friends with in some way, and that you want to spend time with and get to know better. Then invite her to do something with you—go bowling, go to a football game, grab a bite after practice or rehearsal, go for a walk.

As you gain (and exhibit) that genuine, underlying confidence, girls will be even more interested and more likely to say yes. It’s a cycle of good things, a cycle of maturity. It’s part of becoming the kind of man that you want to be.

And if you are interested in having Shaunti speak on kindness for your workplace, church, school or community group, please contact Nicole Owens at nowens@shaunti.com.

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