If I could sit across the table from my teenage self, I wouldn’t start with a lecture. I’d start with a question: Who exactly are you trying to impress?
Because if I’m honest, I spent a good chunk of my teenage years living for an audience that wasn’t even paying attention.
I worried constantly about what other people thought. I filtered decisions—especially dating decisions—through the imaginary court of public opinion. If I had a dollar for every night I stayed home instead of going out with a perfectly kind, funny, interesting “unpopular” girl, I could probably fund a modest Hawaiian getaway. Not first class. But window seats, at least.
I can think of a dozen girls who would have been fun to date. A couple who, in hindsight, probably should have been actual girlfriends. Instead, I let hallway commentary and locker-room wisdom guide my choices.
And what was that wisdom based on?
Complexion.
Height.
Weight.
Whether she played the “right” sport.
I once liked a girl who was a competitive swimmer. Strong. Disciplined. Focused. My friends convinced me that dating someone physically stronger than me was somehow a threat to my masculinity. As if the relationship was going to devolve into arm-wrestling matches at lunch.
The truth? Most of the guys I was trying to impress didn’t have girlfriends either. We were all pretending to be experts in a class none of us had passed.
Looking back, I can’t even identify what I was so afraid of. A raised eyebrow? A sarcastic comment? The dreaded phrase, “You’re dating her?”
Here’s what I’d tell that kid now:
Most opinions are background noise. They’re data points, not verdicts. Sure, if someone says, “That girl just got out of prison,” you might want to do some due diligence. But superficial critiques about appearance, popularity, or social ranking? That’s cafeteria chatter. It evaporates by graduation.
The saddest part isn’t that I missed out on some teenage dates. It’s that I outsourced my courage. I let other people’s insecurity dictate my choices.
I’d tell that younger version of me to grow up a little faster. To understand that confidence isn’t built by conforming—it’s built by choosing. To take the nice girl to the football game. To sit at the table that makes you laugh instead of the one that makes you anxious. To stop measuring worth by applause.
And maybe most importantly, I’d tell him this:
The people whose opinions you’re afraid of right now? In thirty years, you won’t even remember half their names.
The girl you were too scared to ask out? You’ll remember her.
So go have some fun. Be kind. Be brave. And stop listening to the peanut gallery.
I’d tell today’s kids the same thing.
Copyright © 2026 Doug DeBolt.









