How to Get the Girl: What I tell the Young Men I Teach.

It'll work...eventually

About a week ago, one of my former students we’ll call Chris came to visit me after school. We dapped it up with a bro hug and then he plopped down into one of the comfortable rolly chairs I keep in my office. I gave him a grin and asked how everything was going. He said all good. Then I grinned even wider and asked if he was dating anyone yet. He said, “Oh don’t even start.” Then he smiled and we both had a laugh.

I teach 150 students a year. But I’d say there’s always about two or three young men I truly mentor. These are the students who for whatever reason gravitate towards me. They spend extra time in the gymnasium when they should be elsewhere. They go to after school weightlifting. They ask me questions about life, not class. Generally speaking they're usually nerds who remind me of myself in high school. These are the guys I develop special relationships with that go far beyond the reaches of graduation. Chris is one of those guys.

He said, “So there’s this girl I like that I’ve been going running with.”

“Woah woah, props mah man. You’re going running with her? How’d this happen?”

“Well…she ugh…said she wanted to start a running club and uhh….she invited me.”

“Okay! Okay! So how’d you meet her?”

“She’s in some of my classes and we started hanging out. She’s even part of a weightlifting group that I’ve started at my college.”

“I love hearing this. So, have you asked her out yet?”

“Uhhhhhh no.”

“Why not!”

“Uhhhhhhh just uhhhhh, it's just not the right time yet.”

“Does she have a boyfriend?”

“No.”

“Did she just break up with a boyfriend?”

“No.”

“Then I don’t get it dude. Why haven’t you asked her out yet?”

“It’s just hard man, I don’t want to ruin anything.”

I laughed. “Do you know what the friend zone is?”

“Yes.”

“Do you want to be in the friend zone?”

“No.”

“Then you need to ask her out.”

He gave an exasperated sigh, “I know I know…I just….I don’t want to ruin anything with her! I like being her friend.”

I gave my own exasperated sigh. This conversation was an extension of conversations we had all throughout his senior year. Take a chance I would say, and then he would usually say he would…and then report back that he didn’t. To make things more frustrating, Chris is a combination of tall, broad shouldered, well dressed, and little to no confidence. To be fair, he does have a lazy eye, but he’s the one who stresses about it the most. He’s an infuriating pupil sometimes.

I paused and gathered my thoughts.

“Chris, what happens if you ask this girl out and she says no?”

“Then it’ll be awkward. She might not speak to me again.”

“You’re right. That’s definitely a possibility. But you know what happens outside of that?”

“What?”

“Nothing. Nothing happens. I mean sure, it’ll sting a bit. Shit, maybe it’ll sting a lot. But at the end of the day you’d be in the exact same place you are right now. A good looking single guy, working out and going through college. This is a good place to be.”

“Yeah but–”

“--Yeah but nothing. Look, let's say you don’t ask her out.” I put on a mocking tone of voice, “Let’s say you decided to be friends.” I do air quotes with my pointer and middle fingers. “Would you ever really be satisfied with that relationship? Would you be cool just sitting next to her at lunch, having a conversation, and wondering all the time what would it be like to go on a date with her?”

“No.”

“Then I’m not sure if you really have a choice. If you ignore this feeling, and you don’t ask her out…you’re going to be incredibly frustrated. And it’s going to be because you didn’t shoot your shot in the first place. God forbid you decide to just “be friends,” and then you watch some other guy ask her out. That’ll eat you up inside worse than a rejection.”

Chris sighed, “I know. I know.”

Silence settled into the office, and two thoughts struck me at the same time. One was an upsetting stat. Something like 40% of men under the age of 24 had never asked a girl out face to face. They would swipe right, or text them, or slide into their DMs…but damn near half the younger side of Gen Z has never asked a girl out face to face. With Chris’s lazy eye I thought it likely he contributed to this stat.

The second thought was a scene from Game of Thrones where the dwarf, Tyrion, meets Jon Snow for the first time:

“You're Ned Stark's bastard, aren't you?”

Jon felt a coldness pass right through him. He pressed his lips together and said nothing.

“Did I offend you?” Lannister said, “Sorry. Dwarfs don't have to be tactful. Generations of capering fools in motley have won me the right to dress badly and say any damn thing that comes into my head.” He grinned. “You are the bastard, though.”

“Lord Eddard Stark is my father,” Jon admitted stiffly.

Lannister studied his face. “Yes,“ he said. “I can see it. You have more of the north in you than your brothers.”

“Half brothers,” Jon corrected. He was pleased by the dwarf's comment, but he tried not to let it show.

“Let me give you some counsel, bastard,“ Lannister said. “Never forget what you are, for surely the world will not. Make it your strength. Then it can never be your weakness. Armor yourself in it, and it will never be used to hurt you.”

It’s what he does. He drinks and he knows things.

It was time to give my own version of Tyrion’s counsel. I interrupted the silence and said, “Chris you gotta own the fact that you’ve got a lazy eye.”

“What?”

“Yeah man, it’s not like it’s ever gonna change. Make it a part of you.”

“How?”

“Just own it. Look, go up to her and look her in the eye.” He winced at the thought, but I demonstrated by rolling up my chair and looking at him with my most confident smile, “then say something like, hey, let me ask you something. I like that you’re into fitness and I enjoy the conversations we have. I’d love to take you out. And don’t worry about the eye over here, he’s just keeping a lookout. Making sure no one comes to rob us. He’s always on patrol.”

Chris paused for a moment. Then he said, “Damn. That’s actually pretty good. I feel like I could work with that.”

“Right? Just own it. It's yours. Might as well be proud of it.”

Chris cracked a grin and said again, “That was really, really good.” Then his buddy Johnathan knocked on the door and asked if he was coming out to play soccer.

He got up and thanked me on his way out the door. I yelled at him to ask the girl out.

Hell. Who knows. Maybe this time he’ll actually do it.

---

Conversation Reflection:

Well…the line I gave him about his lazy eye is only as good as its delivery. It’s only as good as his projection of confidence. He doesn’t have that yet so…

He’s probably going to crash and burn.

Likely rejected. Likely friend zoned.

Still, I think the conversation was good advice.

I’ve had my own journey of figuring out this particular area of becoming a man. I was in a relationship from 20-29. When it ended, I entered the dating pool with the same skill set I had when I was 20, essentially the same age of the boys I’m giving advice to. I had to learn how to deal with rejection, I had to get over the fear of approaching someone I found attractive.

I remember one of my first attempts was talking to the girl who worked at Barnes & Noble. I remember asking her about a book with the intentions of asking her out. I didn’t. I bought a book I didn’t want and fled the store.

I remember hating the fact that I was a coward. I had to fix that feeling. I drove back to Barnes and Noble the next day with a note in hand. When I saw her my heart started hammering behind my ribcage. When she saw me, I gave a weak smile, and approached her with the note, “Uhhh, hey…uhhh, here. I’d like you to take this.” She smiled uncertainly and took the note. I turned around and made a beeline toward the exit.

The first line of the note said, “So, I couldn’t quite get you out of my head after I met you yesterday…” And then I recommended reading a specific page in a book called “American Gods” which was in the store at the time. I wrote that it was one of my favorite passages in all of literature. Then I ended the note with my number.

I checked my phone for the rest of the day like a crack head. Every vibration sent my hand shooting into my pocket. No luck. I was bummed, but I was also somehow satisfied. I turned over a stone. I took a chance. I asked a girl out face to face…at least kind of.

Somehow I wasn’t dead.

The next day, I received a call from a random number. When I heard the girl’s voice on the other end, I cracked a grin and, like an idiot, I said, “holy shit it worked!” She laughed and told me the note had made her day. She also told me she read the page I directed her to and now she intended to read the book.

Then she told me she had a boyfriend.

My heart sunk, but I told her I should have figured. I said if the situation ever changed I hoped she would reach out. She said for certain. Not the outcome I wanted. But somehow not a bad experience either.

Whether you’re trying to get laid or actually fall in love…

I say take the shot.

Try.

Be embarrassed.

Get your heart trampled on a bit.

Whether Chris wins or loses, in any case, he’ll learn. Much like I did.

That’s what I hope he takes away.

---

*4 years ago, I read Kevin Kelly’s article, “1000 True Fans.” The gist of it goes like this. Create a following of people who become fans of what you do. Be so damn good at what you do that people want to give you money so you continue doing it.

Here’s what I do. I teach, and I write stories about it.

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