People Are Sharing Their Biggest, Most Heartbreaking Teenage Regrets

Kasia Mikolajczak
to set of teenage legs wearing sneakers
Unsplash | Aedrian

I'm always intrigued when people say they have no regrets in life. I wish I could say the same. There are a few things I would have changed if I had a chance, alright. And as it turns, so do other people.

When a recent Reddit thread asked, "What was your biggest teenage mistake?" I was really interested to see how other folks answered. So let's take a look at what they said. Come on!

This General Health Issue

blue ear plug in somebody's ear
Unsplash | Mark Paton

"Not taking care of your body in general. For example, I'm 30 and my hearing SUCKS after too many gigs without any ear protection. I work in construction now, and I'm the only one on-site who wears ear defenders. My hearing is already bad enough without making it worse. The lads I work with will be regretting not wearing them later on in life when the awful tinnitus gets them. Your ears, eyes, lungs, gut, etc. will thank you for every good decision you make."

I so agree with that. You only have one body, no?

This Personality Trait

three guys laughing
Unsplash | Jed Villejo

"Trying to be someone who I wasn't."

Oh, yeah. I see people do that a lot. It usually happens when you want to impress somebody or a group of people, and it spirals out of control. It's always better to just be who you are.

This Realization

woman raising her hand in agreement
Giphy | Red Table Talk

"Not realizing that my parents weren’t doing the best job raising me/preparing me for adulthood and realizing I should maybe take matters into my own hands."

I think many of us can relate to that. Some parents are really good at that and others, not so much.

This Mistake

person's mouth being examined by a dentist
Unsplash | Caroline LM

"Not taking better care of my teeth."

Having been to the dentist three times in two weeks, this hits hard, haha. I've done the best I could have, but still, I probably could have done better in this department myself.

This Bad Habit

cigarette butt on a ledge
Unsplash | Andres Siimon

"Oh god. I was just sitting here smugly thinking 'at my age I’m pretty content with all the mistakes I made as a teenager' but yeah. I smoked a pack a day for almost 30 years before I finally kicked it."

That's always a hard lesson to swallow.

This College Trap

students throwing caps in the air at graduation
Unsplash | Vasily Koloda

"I went to college at 18 and wasn't ready for the experience and wound up wasting a couple of years drinking/partying. If I had just not gone straight to a four-year and gotten a job for a couple of years and lived with my parents or even compromised and gone to a junior college and worked part-time on the side, I would have had tens of thousands less in debt to pay off in my 20s and early 30s."

I feel like a lot of people take this path and regret it later.

These Stereotypes

a guy at a convention
Unsplash | MarĂ­lia Castelli

"I took teenage stereotypes too seriously. Like, I thought the kind of dynamics you saw in teen moves were real: jocks were all dumb a-holes, nerdy kids were smart virgins, etc. It took me an embarrassing amount of time to realize that people are people and that I was severely limiting myself by assigning myself a 'role.'"

Oh, wow! Too many John Hughes movies, huh?

This Lesson

man giving a pick up line to a woman
Giphy | Martin

"Never having had the courage to pursue girls or ask for help in figuring out how."

I guess there's a bit of an art to that. I can sympathize with guys who aren't natural at doing that. It can't be easy to be the one who's always pursuing, huh?

This Negativity

woman with a grimace
Unsplash | OSPAN ALI

"I was a rather negative person as a teenager but tried to play it off as sarcasm instead. I somehow had grown into this weird bubble where I made fun of almost every little thing, but didn't really realize that I was also hurting my friends by doing that."

"I did lots of growing up after high school, and I'm a bit sad about not keeping in touch with my old friends. They might have liked me more today than they did back then."

True dat!

This Path

woman saying "It's kinda like you're waging a war on fun."
Giphy | CBS

"I didn't let myself have much fun. I always thought about things like I was already an adult and always had to be responsible and mature. There are a lot of things I passed up that could have been really fun had I just let myself enjoy life a little."

Ah, that's sad.

This Mismatch

two people holding hands
Unsplash | Brooke Cagle

"Forcing myself to fall in love with someone. I didn't love her; I was in love with the idea of a girlfriend. Now to be fair, she made the same mistake. She didn't love me. It was a bad relationship."

I guess these two were just in love with love and not with each other, huh?

This Relationship Drama

Rory from Gilmore Girls saying "too much drama."
Giphy | Gilmore Girls

"Jumping from relationship to relationship. Part of me wishes I could’ve explored who I was without someone attached to me. I was too emotionally immature to even handle serious relationships. Now, I feel like I hurt some people, and was hurt by some people — all of it unnecessary. I did, however, end up meeting my wife and mother to my beautiful daughter."

"I don’t regret that at all. However, it would’ve been nice to end up in the position I’m in without all the teenage stupid drama."

I hear you loud and clear.

This Scare

two girls on the beach laughing
Unsplash | Dominic Sansotta

"Being afraid of girls. Didn't realize that they were normal humans too, who just wanted to have fun and be liked. They were mysterious and scary, and I lost a lot of years being self-conscious and shy."


This Bad Relationship Choice

Simon Cowell covering his face with his hands in shock
Giphy | X Factor Global

"I dated a 31-year-old when I was 18 for a year and a half. I still cringe. 'It's because I am soooo mature!'... yeah no. That's not how that works. I apologize you went through that. Also 0/10 would not recommend dating an adult when you are a child. I am 32 now and can't believe someone would date an 18 yo at this age. They are so young and wet behind the ears still."


This Bad Decision

person driving a car
Unsplash | Alex Jumper

"Driving under the influence when I got my first car. I used to drive when going out with friends under the guise of not drinking, but inevitably, I would end up having a couple of drinks and would drive home anyway. Never got drunk to the point of being a severe danger behind the wheel, but it was still stupid as hell."

Thank God nothing bad happened.

This Missed Opportunity

man shaking his head in dread
Giphy | Yellowstone

"Not getting the hint that my friend, the beautiful Patricia, wanted to be WAY more than friends."

Aw, I bet this lad is really kicking himself now. Now I'm so invested in this story, haha. What could have been!

This Lack Of Confidence

person covering their face with their hands
Unsplash | Priscilla Du Preez

"Not having a little more confidence. It held me back from enjoying life for a really long time."

I think that's something that happens to a lot of people. Not everybody is born with confidence. Some of us need to work on it, so don't beat yourself up about it.

This Sad Truth

woman holding a mug that says "choose kindness."
Giphy | The Prepared Performer

"My biggest teenage mistake was not being kind to myself. My teenage years were some of the hardest in my life: trauma after trauma, disappointment after disappointment — and I always blamed myself for them all. It wasn't until recently that I could start looking back and realize that it really wasn't my fault. I did a lot more than most would have in my situation. And even though I had terrible teenage years, it's not a reflection on who I am, but more a reflection on what I was going through."

At least, this person sounds to be in a good place now.

Wow! Those are some confessions, huh?

four teenagers sitting at the beach looking out into the water
Unsplash | Amir Hosseini

I'm sure many of us have things we regret doing or not doing when we were young. Am I right? The bottom line is whether you're a good human being now. Those mistakes are in the past, and as long as you learn from them, it's all good. Do you have anything you would have changed about your life?