27 Of The Most Shocking And Heartbreaking Regrets People Have From Their Teen Years

    "Looking back at the way I bullied this one girl, I was cruel and thoughtless. I’m 50 now, and it still hurts me."

    I've always believed everything happens for a reason. But looking back, we've all have made small or big decisions when we were younger that we wish we could change now.

    So, recently, this viral thread where a Redditor asked the internet, "What was your biggest teenage mistake?" had people sharing the mistakes they made during their teen years that they'll never forget — and it will pull at your heartstrings.

    kid covering his face with his hands in despair

    Here are some of the most eye-opening ones:

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


    a teen on the couch talking to their mom

    2. "Having a phone. It wasted 10 years of my life (still going) and negatively impacted everything from my social skills to my overall intelligence. I'm 19 years old now, and I don't feel like I'm ready for real life: having a job, having a girlfriend, buying a car, etc. It just seems like too much for me."

    "I'm still to this day wasting my life away on my phone while missing out on so many experiences."


    person on the floor on their phone

    3. "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."

    "Look after your body — it's the only one you've got. It will repay you for every good decision you make and definitely remind you of any bad choices."


    someone working with wood

    4. "Looking back at the way I treated this one girl, I was cruel and thoughtless. I’m 50 now, and it still hurts me."


    "My wife is 50 and her elementary/middle/high school bully tried to apologize to her 12 or so years ago, and my wife just told her to go f**k herself. Whatever that she did to her really stuck with my wife. There were no anti-bullying programs back in the '70s and '80s. I think our schools actively encouraged bullying (some of the teachers were absolutely bullies) to 'build character.'"

    "On the other hand, a dude who kinda bullied me in high school apologized to me around the same time (maybe a year earlier), and I accepted it because he really turned his life around. My niece later had the guy for a class and told me that he tells students about how horrible he was to people when he was younger and encourages his student to not follow in his path."


    student crying and leaning against a wall

    5. "Getting waaaaaay too hung up on someone and being kinda creepy about it. It was a pretty nasty awakening once I realized that I was making them uncomfortable and that I needed to stop. Thankfully, I had the good sense to just spend a year working on myself and figuring out how to be, like, emotionally healthy."

    "Reevaluating your preconceptions and biases is really awful work, but I will say, it's well worth it. It made me much happier in the long run, and got me past most of the worst of my dating troubles. Plus, I might have dodged becoming an incel or something. I don't know if I ever would've gotten that bad, but in retrospect, I think I might've once been vaguely on that path. I just wish I could undo being creepy towards my friend. That's harm I've done that I'm not really ever gonna get back or be able to fix."


    guy and woman talking outside

    6. "Marrying my 18-year-old self to a 40-year-old who'd been grooming me for three years, just to spite my mother."

    "0/10, would not recommend."


    hands taking off a wedding ring

    7. "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 realized 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."

    "It makes coming to terms with losing out on that part of your life much easier. I wish I had this mindset much earlier."


    person on a subway

    8. "When I had the opportunity, I didn't pursue a higher education, but decided to go to work right away."


    someone doing homework

    9. "Funny enough, my big regret is focusing on my studies and putting off getting a job way too late."


    "I went to college at 18 and wasn't ready for the experience and wound up wasting a couple years drinking/partying. If I had just not gone straight to a four-year and gotten a job for a couple 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."


    people clinking their glasses

    10. "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.'"


    letterman jacket

    11. "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."


    hand on top of another

    12. "I took my uncle's beautiful restored classic car for a drive when I didn't have a license and got it impounded."


    classic convertible car

    13. "Not being more sociable. I’m 25 now, and I have no idea how to make friends."


    "I was quite social as a teenager, but over the course of my 20s, I lost interest in putting a lot of effort into it. I just stopped caring about what others thought of me, and realized a lot of the 'friends' I had were shallow relationships with people who didn’t give a crap about me."

    "So it can be tough, and now all I want to do is focus on what and who is important to me."


    two people looking at a phone

    14. "Coasting through school on being bright and never learning to study. University was a shock and just about managed my 2:2."


    "Not building study habits. Being an ex-gifted kid, I never had to study in school. Come university and everything is spiraling down. Learn how to study, kids."


    open book and notebook on a table

    15. "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."


    group of teens sitting on a bench

    16. "Trying to be more mature. Since childhood, I prided myself on being an extremely smart person who was above things like 'cartoons' and 'playing.' Of course, I still liked those things, but I desperately tried to hide it even though literally nobody actually cared."

    "Even though I'm older now and know that people don't care, I still find myself tabbing away from cartoons and pausing games when people try to see what I'm doing. That instinct is still there. I usually just force myself to resume what I was doing, but I feel like I'd be better off if I didn't have the desire to prove myself to others as a kid."


    teen playing video games

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


    "Most of us have experienced this at some point. For me, it was the lovely Imogen. I knew her from us both having a paper round at the local newsagents. We first met when picking up our papers. I asked her about her unique accent. It turned out that she was deaf, and had a cochlea implant. It made for an awkward, but giggly and apologetic moment. We ended up chatting a lot and connecting instantly. I was just grateful to have her as a friend as I was a loner at school, and she was at a different school. Months later, she admitted that she really liked me on MSN Messenger."

    "She was a short walk away, and I said that I would come over. I remember her at the doorway, looking visibly shaken, not sure what to do. We went for a wander and chatted about just about everything — except what she said. We walked back by hers, she went home, and I kicked myself all the way home for not saying that I liked her back — something that I hadn't really realized until then. But I didn't have the guts to turn around, and our friendship sort of fizzled out.

    School ended, and she moved away. She has vanished from social media, so I haven't had any communication with her in many years. And no, this story doesn't end with 'I've since found my true love.'"


    hands holding a paper with a heart drawn on it

    18. "High school football. My doctor advised me against it, but I was 14 and 'knew everything.' Putting my body through four years of abuse was not worth what I got out of it. Today, I’m 33 and wake up with a stiff neck every day. My right shoulder has a ton of scar tissue, my elbow has a bone chip, my jaw clicks/pops if I open it too wide, and both of my knees ache when it gets too cold."

    "Also, our team sucked."


    football players stretching

    19. "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."


    person dancing in the middle of a circle

    20. "Not taking better care of my teeth. You have to floss. I always brushed my teeth but never flossed. Ruined my teeth. I’ve had to have many dentist appointments to fix cavities in between my teeth. I’m only 28, and my teeth were rotting from the cracks in between."


    "Adding to this: Not wearing my retainer after braces. My teeth slowly moved back into wonky OG position in about a year and a half. Total waste of time and money for my parents."


    close up of teeth with braces

    21. "Treating high school as an obligation and not an opportunity. Not just social but economical gains and your own development are way greater affected by how you view your high school years."


    someone opening their locker

    22. "Spending a large inheritance I got when I was 18 in 2009. I could have owned a property by now."


    person entering card info into their computer

    23. "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."

    "When we started dating at first, things were fine because it was the honeymoon phase. But an element that caused trouble was that her mother didn't like me. I wasn't her kind of person, and she had trouble letting go of her daughter; we clashed in that she would always try to change me, my appearance, and my behavior, and she hated my friends. And one of the biggest issues between my girlfriend and I was that she was jealous of any other women who looked at me. I'm not blameless in this either; I lied to her about if I talked to another woman, stopped hanging out with friends, and changed everything about myself to please her. 

    We almost broke up more times than I can count: Every few months or so, it was usually her trying to break up with me, but it never really ended our relationship. I tried breaking up with her a few times, too, because it just felt like we were too afraid to leave (not that I knew that at the time — at the time, I was probably thinking something more like this isn't going anywhere). Eventually, she did break up with me, and it took me some time to realize that I was never really in love with her, but more with the idea of status/having a girlfriend. It wasn't until I started getting over the whole thing that it became clear to me that we didn't seem to like each other all that much — that's why we fought as much as we did and had issues about the most random things. Ultimately I think it was a mistake, but I don't hold it against her or myself anymore. We were teenagers after all, and it's common to make mistakes like that."


    the back of a woman's head

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


    close up of a guy looking in the mirror

    25. "Not focusing on good friendships. I used to hang out with some douchebags, but I don't have a single friend from my high school days anymore. Granted, I moved about 3,800 km away, so it's hard to stay in touch on a meaningful level."


    close up of someone on a video call

    26. "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 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."

    "My 33-year-old self shudders now at my own idiocy."


    hands on a stirring wheel

    27. "Being an absolute a-hole to my best friend. She didn't deserve that — I was...abusive towards her. And the worst thing is that, until I was really going to therapy and working on myself (which wouldn't happen for a few years after graduating), I didn't understand why she stopped talking to me, and I was mad at her for it. I look back on what I did back then — that I didn't even register as bad or mean at the time — like, I made fun of how she ate, I stole food from her, I would slap her arm a lot harder than could be explained away as a friendly tap, I talked her into numerous situations she was uncomfortable (and very clearly so) with. I made fun of her for wanting to stay a virgin. I was a piece of f**king sh*t. All of that is just scratching the surface. I know, in retrospect, that I made her feel incredibly unsafe on multiple occasions. And the thing is, is that I didn't START to come to that understanding until I was around 23."

    "That was five years after she stopped talking to me. For that entire time, I didn't understand why she had stopped talking to me, and I was upset over it. It wasn't for another three years of therapy that I fully came to an understanding of just how awful I was. Most of those three years were me trying to excuse my actions with every reason under the sun and my therapist, who had the patience of a saint, calmly shooting down every excuse and diving into why I thought it was a viable excuse.

    This is a big part of why I advocate that while disabilities, neurological issues, and mental health issues can help EXPLAIN why a person acts a certain way, it doesn't EXCUSE the harm that they do due to those actions. Trying to reach out to her to try to apologize seems cheap now; what can you say for a situation like that? I'd really rather not dig up the past for her — she doesn't deserve that. She's moved on with her life, and frankly, I'm incredibly glad that her life doesn't involve me. She didn't deserve what I put her through, and she deserves to be happy."

    two friends

    What was your biggest teenage mistake? Let us know in the comments below.

    Note: Some responses have been edited for length and/or clarity.