April 15, 2020 | Jess Silverberg

People Share The Messed Up Things They Did As Teenagers

Our teenage years are perhaps the most formative years of our lives. It's a time for personal growth, both physical and emotional. Almost never is it a smooth experience. Here are some of the messed up things people did as teenagers:


#1 Ghosting Remorse

I played with Omegle. It was very fun, then I got into a “relationship” with a 15-year-old mom. I didn’t actually know how to handle relationships since I was only 16, so even though she told me she loved me, I ended up ghosting her because I was too stupid to know how to maturely end things. Ghosting isn't a good way to break up and anyone who does (including myself) is a jerk.


#2 The Waltzers

If you guys know the ride called "The Waltzers," which is always there at UK fairs. There was a sign that said “Topless girls go free,” so my friends and I went on for free “for a laugh.” We were teens, under 18, and the ride worked by men spinning the seat things by hand. They took photos of us whilst spinning and there was nothing we could do about it. We just laughed at the time. It didn’t feel messing up then, but knowing some guy somewhere has photos of me topless just so I could save $4 feels a bit messed up now.


#3 Rebellious Phase

I argued with my dad constantly. I feel awful about it now. My dad had a temper, but mostly, I was just a little jerk in my rebellious phase. Now that I'm an adult, Dad says I'm the child of his that he relates to the most, and that meant so much to me. I idolized my dad when I was a kid, I was a terrible asshole to him as a teenager, and now I'm back to my dad being my hero.


#4 Lesson Learned

I stole money out of one of those donation cans at my job for kids with cancer. I only got caught because the woman who comes to collect it each month noticed it was pretty empty so my bosses checked on it more and caught me on the CCTV when I wasn't being sneaky enough. I totally messed up on my part. I was fired. They didn't press charges and I did return the money, plus more.


#5 Desperate Days

In desperate days, I used to sleep in a Catholic Church that was left unlocked at night. People would come in occasionally to pray and light votives at odd hours, and I’d see them from the balcony where I slept. Beneath the votive table was a built-in offering slot where people could deposit money for offerings. After people would make offerings, I’d go down, pull out the pins holding the offering box together, and steal the money. I feel pretty bad about that now.


#6 A Bad Call

I live in the boondocks and when I had my graduation party, we needed to put something out at the end of our driveway for people to find us. So... my best friend volunteered to flag people down... we proceeded to duct tape him to the telephone pole, write "party here" on it across his chest, and leave him there for an hour while people showed up. It worked marvelously and we cut him down when we heard police sirens.


#7 Eighth Grade Drama

In eighth grade, my best friend asked me if I would go and ask the boy she liked if he liked her and if he would go out with her. I went over and asked him if he liked her, he said no, then I asked if he liked me, he said yes, and then I asked him to be my boyfriend, and he said yes. Then I went right back to my friend and told her that he didn't like her, but that he liked me and was now my boyfriend. I don't know why I did that.


#8 An Innocent Joke

A few things. One thing that came to mind was wielding a wooden sword out of a car window and screaming at a classmate, as a joke of course. I didn't realize there was a cop approaching the school as we were pulling out of my high school. The cop forcibly removed me from the vehicle, threw me in a snowbank and arrested me in front of my high school. Luckily, the charges were dropped and it's now a funny story.


#9 The Obvious Lie

At the age of 13 years old, I took the keys to my parents' Jeep and went joyriding through the neighborhood at 3 a.m. All was well until I was speeding down the road in front of my house and lost control of the car going towards the end of the cul de sac. By some miracle, instead of flying off the cliff at the end of the cul de sac, I slammed into my neighbors' big concrete mailbox, breaking it in half, but saving my life. Amazingly, the car still worked. The radiator was a bit busted, but it still drove.

I was so nervous putting the car up that when I was pulling into the garage, I accidentally hit the gas instead of the brakes, crashing into a little storage room in the corner of the garage. The next day, everyone was wondering what happened. Me, being so smart, I said I was skateboarding in the garage and ran into the wall, destroying the door and wall of the little room. I still have pictures. It didn't take long for my parents to know what had really happened, as my story was an obvious lie. This was about 16 years ago now.


#10 Justice Not Served

There was a guy that I freaking hated at work. Just a real dirtbag kind of guy. Well, my work only has one restroom. I was finishing my business and I heard a knock at the door. It was the dirtbag telling me to hurry up because he had to go. I told him I'd be out in a minute. So I grabbed the can of Lysol, pulled out about three feet of toilet paper and sprayed it down a bit. Then I rolled it all the way back. Unfortunately, one of the other guys jumped the queue for the bathroom in front of the dirtbag. For the rest of the day, that dude was scratching his bum and shifting uncomfortably.


#11 The Mysterious Fire

When I was 12 I let a "friend" convince me to break and enter into an abandoned house. About a month later, I was giving a statement at a police station because someone tried to light a fire in a closet there. Either the other kid did it or someone else did and we both almost took a rap for that. I suspect the "friend" because he ended up in juvenile detention shortly after, right before his parents got arrested, and also right after their house "mysteriously" burned down. Shocker, if you keep your meth equipment in a fireproof safe, they discover that pretty fast after a fire, and investigators are pretty good at their job.


#12 Moms Deserve The World

I took advantage of the fact that my mom was emotionally weak. I'd argue with her just to get her to cry and win the argument. I had no appreciation for how great my mom was and the sacrifices she made for me and my brother. Today, I'm not like that anymore, but I wish that I could go back and treat her the way she is supposed to be treated. I won't exchange her for the world.


#13 Love's A Gamble

I was really messed up mentally after my best friend broke my heart and ghosted me. I started seeing a 42-year-old man when I was 17. I didn’t think it was a big deal at the time, but that messed me up even more. A month after that, I got into a relationship with a 23-year-old who was homeless and jobless. I would sneak him into my parents' house every night. He turned out to be emotionally abusive. I didn’t get out of that relationship until I was in college because I moved to a different city.


#14 Not The Way

I was living in a group home for six months and there was one girl who was a total witch. A lot of us were going through stuff and we could’ve been just as hostile, but for the most part, we all just defaulted to friendship except her. So, as a courtesy to her to make her cognizant of what would happen in the real world if she kept treating people the way she treated people... I may or may not have put Nair in her conditioner... 17-year-old me learned fighting fire with fire is not the way.

#15 Dodging A Bullet

This is more of an almost did... When I was 16 or 17 and finally realizing I was gay, I started chatting with a lot of different men online, including some guy who was in his 20s. He was also not out; we lived in a fairly rural area, so I guess he was discreet. When the weekend came, I chickened out and went to a friend's for the weekend. My roommate called me a day or two into the weekend and said some man had been calling our house phone asking for me, but wouldn't say who he was.

I didn't respond to any messages he sent me, and then eventually he sent me a pretty ominous, threatening one suggesting outing me or something along those lines, so I finally wrote him back saying I regretted our convo and that I didn't think we should talk. He explained that he only wanted a response as he didn't want me to out him, either. Thankfully, that was the end of it, but it was a pretty risky thing I almost did. The guy freaked me out big time and who knows if he was even who he said he was online.


#16 The Guilty Thief

When I was about 12, I had a short phase of stealing from charity shops and this little sweet shop in my town. I still feel really bad about it now... I was old enough to know better, but I liked the thrill of it. I’m going to donate to charities whenever I can when I’m an adult, but I don’t think the guilt of it will ever leave me.


#17 Psycho In The Making

I'm glad I stopped because it could've really turned into something worse. I used to catch those black widow spiders around the house and put them in a glass cup. Then I would put the glass cup on a frying pan with the cup opening on the pan, so the spider would be touching the pan. I would then proceed to light the gas stovetop and watch the spider "dance" it's way to death. I did this to at least 30 or 40 spiders. I still feel bad. Never got caught either.


#18 A Three-Year Lie

I lied to my parents for three years about dating a boy I said was gay. When I broke up with him, he got very abusive and the school had to get involved. When my parents found out, I told the school they were verbally abusive to me (I didn't lie, I just said the right things at the right time) and social services got called. Nothing serious happened to my parents, but they tested me without my consent.


#19 Hospital Dash

I jumped off a five-story building while tipsy and depressed. I broke a hand, foot, and some ribs. I woke up in a hospital the next day where I was advised I was not allowed to leave. They didn't have my ID or name so I got out of there by stealth. I cut off my casts with a hack saw three months later. It was so I didn't have to pay the hospital bills.


#20 Standing Up

My family had very little money when I was in high school, and I went through most of my days without eating lunch. I would just wait until I got home and have some cereal or something. In my first year of high school, a big bully tried to take my fries. It was the only time I ever bought something from the cafe, so nobody was going to take my fries. I was a small, nerdy guy with pimples and glasses. Just the fact that I didn't let him take any totally impressed my friend. Good move. The bully backed down.


#21 Defending D&D

One time, this guy didn't like Dungeons and Dragons and he bullied me for it. I punched him in the face in retaliation. I'm supposed to have counseling now because my teacher is concerned about my behavior. This was only a few months ago and now and then I regret what I did. It changed people's perspective of me.


#22 Risky Business

When I was 17, I used to dress very provocatively and wear lots of make-up to make myself appear older. I'd sneak into bars and clubs with my friend who would do the same, and we would just wait for guys to buy us drinks. We lied about our ages and flirted with guys in their early 20s. We completely took advantage of them, just to get free drinks and get wasted. I now recognize how stupid and dangerous that was. What the heck were we thinking?


#23 Bad Holiday Spirit

My friends and I would roam a few neighborhoods over and we would tear down people's Christmas lights. I have always regretted it and wish there was some way I could apologize and make restitution. It was the late-'70s. I know... it seems like something straight out an old movie with bad teenagers messing around.


#24 Catty Issues

I was dating an older guy while I was in high school. His younger sister was a grade or two above me and she was a witch. She was straight out of an episode of Hoarders. Her room and it was absolutely filthy. So one day, she brought home a kitten and I was steaming mad because she was not going to take care of it at all. And sure enough, once the novelty wore off, I would be the one cleaning the litter. Because it was locked up away from people, it was basically feral and would lurch out to attack everyone in the house.


#25 Karma Came Back Around

There was a really annoying kid who kept pestering me to get him illicit substances. I wasn't even involved in any of that. After a couple of weeks of this, I created fake ones for 100 bucks. Turns out, he didn't want to do any, he just wanted to be a hustler and make money. This resulted in him getting his butt kicked after selling it all to unsatisfied customers at the club. Don't worry, karma came back and whooped me just as hard in the proceeding years.


#26 Bad Judgment

I had no internet access at home so I used to go to my friend's house to log into chat rooms. When we were 14, we agreed to meet up with a 24-year-old man we met online. We willingly got into his car and drove around with him for a while. Then I started feeling uncomfortable and made an excuse to go home, but my friend wouldn't come with me, she wanted to stay with the guy. I don't need to go into details about what happened to her but I still feel bad about it.


#27 Bust Your Windows

I smashed out some guy's car windows because he duped my friend for her $20. But I guess, in my defense, the jerk ran off with her money. She went to my house crying, bent out of shape, and told me what happened. So I told her to take me to his house. That's where I picked up some rocks and... well, there you go. Hopefully, that taught him not to steal from young girls.


#28 Keyboard Bandit

In 9th grade, my french teacher forced me to do corrections for her on lunch hours to pass her class, as I had not handed in most of the assignments. For some unknown reason, I had enough of this and decided that the best solution was to destroy her keyboard on my last day of correcting stuff. Why I did this, I do not know. I was a tubby little shy kid, and I never acted out. As the classroom was unlocked during lunches, I was never accused of anything. I forgot about this until ten years later it came back to me when I was discussing high school with friends. My friends howled and it's still a running joke in our friend group that I "break-in" new keyboards for them.


#29 Auntie's Secret

I got my wisdom teeth removed and they gave me Vicodin for the pain. my mom was going out of town for the weekend, so her sister was staying with me in case I needed anything. I decided to set a few of the Vicodin aside for a rainy day. When my mom got home, she counted them and accused her sister of stealing them. That's how I found out my aunt had a problem. I never said anything.


#30 Revenge By Superglue

In high school, I got really upset at someone I had been friends with, so I decided to crazy glue his locker shut. The catch was I used three tubes and did it right before spring break, so it had over a week to set. I not only did the hinges and the lock, but I also went around the perimeter of the entire door. They had to cut the front of the locker off for him to get his things.


#31 Bullying The Bully

This kid that lived down the street from me used to bully me on a regular basis. Long story short, one day, a few of my friends and I went to his house. They were out of town and didn’t lock the doors! We stole all of his baseball cards, drank his milk, etc. Actually, the place was already messed up before we got there... As an adult, I realize that was probably why he was a jerk. Anyway, I got caught because we did this like three times. His neighbor told his parents they saw us going in and out of his house.


#32 Not The Answer

I kind of asked my boyfriend to fight my classmate and he broke my classmate's arm, just because he splashed me with a half-full glass of water and ran away. Well, I splashed him with a glass of juice in front of the dining hall as revenge, and he chased me and tried to drive my face into the concrete stair step, but I managed to turn around, so he proceeded to choke me, all while screaming obscenities. He deserved being beaten up at the end of it all, and breaking his arm was unintentional, but I myself acted really dumb regarding splashing juice at him. I should have put chewed gum into his pocket as I had planned first.


#33 Taking Advantage

When I  was still in high school, I used to spend overnights during the summer with an older lady in her house to be an aid in case she needed anything. I'd sneak out most nights and a friend would pick me up so we could get tipsy. I'd also sneak guys in from time to time to hook up. The older lady was very independent so I never got caught; she didn't need much help overnights. But I still regret it to this day... it was a terrible thing to do.


#34 Oblivious To The Signs

When I was 13, my best friend at the time was very depressed and this made her accident-prone. I had to disinfect and bandage her often, and I also remember coming home on the bus with her and when we got off, she admitted to being addicted to her anxiety medication. She started crying and begging me to not call emergency services. I ended up calling her mom to take her to the hospital.


#35 Permanent Guilt

I’ve always been close to my dad. He was single for a long time. When I was 15, he was injured badly at work and spent over a month in the hospital. What did I do? I stole his car and wrecked it. A few years later, I used his social security number to open credit cards and ended up spending $30,000. We’re going on 25 to 30 years on these things now and I grew out of my horrible rebellious phase, but the guilt still kills me.


#36 Sadistic Ideas

I had this friend who loved to screw around at the train tracks. He loved to bring slingshots, take rocks, and bust out the train lights. When that got boring, he decided to up the thrill and started putting things on the tracks for the trains to run over. Keep in mind, these are trains carrying people not just cargo. It started off small with something like paintballs and watching it splatter. Eventually, one day, we found a dresser and basically found a sort of blind spot so that the train wouldn't have much time to stop before it smashed into it. I didn't really think at the time that stuff like that could de-rail the train.


#37 Wasteful Spending

When I was 16, I would tell my mom I was sick and she would call in to tell the school. At around 10 a.m. or so, I would tell her I was feeling better and that I was going to head back to school. I would then go over to my older cousin's place (who I wasn't supposed to hang out with) and we would go to the bar. My father had passed away that summer and I suddenly had a trust income of $1,600 a week with no oversight. I spent so much money by the time I graduated.


#38 Greek Tragedy

When I was 13, I wrote a Greek mythos about why schools have rules for a Language Arts assignment. It involved themes of oppression, dysfunction, and rebellion. That was in 2009. That essay turned out to be a prophecy about what would happen to higher education. Tuition skyrocketed, making students debt slaves (oppression). ROIs started failing with more students failing to secure jobs in their fields (dysfunction).

Students already have started pulling out of the system altogether and have even forced some schools to shut down completely (rebellion). In other words, I was only 13 and I had already doomed the college system. Even my middle school started to deteriorate after the essay, with a massive layoff hitting the district later that year, more fights breaking out, an arson incident with a microwave, and profanities being written into the yearbook.


#39 Dodgy Communication

I downloaded an app where you could send anonymous messages to either guys or girls. I was 16 and very lonely. I started being friendly, then dodgy, and then I ghosted them. Guys would chat for a while and then start asking weird questions. I wasn't so lonely that I wanted to send pictures to a possibly 50-year-old man. I deleted the app soon after. I was kinda sad though, since some of the conversations had promise.


#40 Young Arsonist

I almost burned a neighbor's backyard down. My friend and I were 13 or so and thought it would be hilarious to start a small fire in our "weird" neighbors backyard. Turns out, dry pine needles and leaves are extremely flammable! But instead of trying to put it out, we casually walked home and sat on the curb as the firetrucks rolled by. We got so nervous, we didn't know what to do. Luckily, it didn't get to the house and no one was hurt, but I still have no freaking idea what I was thinking.


#41 Kindergarten Antics

I wasn't a teenager at the time (I was maybe five years old) but I poured a full bottle of water into my teacher's handbag. Her phone was ruined and she had to get a new bag. To this day, she still doesn't know who did it. To be honest, I can't remember why I did it, but I do remember that she was an absolute jerk to me.


#42 A Changed Man

Breaking into houses, stealing stuff... things like that. I was a punk, and I grew up in a rough area. We use to steal bikes and stuff just for fun; just vandalize things. Looking back, I feel horrible about the things I did. I got out of that lifestyle and got a decent job, started a family, and bought a house. I couldn't imagine having my house broken into or having my kids' bikes stolen or Christmas decorations ripped off. Just absolutely horrible things.


#43 Crossing The Line

In high school, we had a Spanish teacher who did not speak English very well and we would play jokes on her. Most of them were harmless such as taking her tape and unrolling it all the way to make a big ball, but I dared this other kid to take #2 from his dog and put it in her desk. He took it a step farther and made brownies. She came in and saw he had made brownies for her, then ate one and got really sick. The kid got expelled and sometimes I feel bad for daring him, but he was the one who made the choice to take it a step farther. I do feel bad about how we treated her.


#44 Finding Faith

I was a spoiled brat living in poverty. As an only child, I would pout until I got my way. I was combative towards my parents to the point of being physical. Thankfully, I found the Lord at around age 14 and realized the error of my ways. I could still be a brat after that, but I learned to bite my tongue and I never got physical with my parents again. I'm a much better person now.


#45 Computer Pranks

In late middle school and early high school, I thought I was really clever and funny. I would go to office supply and 'big box' tech stores like Circuit City and Office Depot and set a screensaver password on their computers so that when the computers went to screensaver, employees wouldn't be able to regain control. It's "mad lad" kind of stuff but with the added embarrassment of screwing over people who were just trying to earn a living.


#46 Painting The Town

I climbed on top of a J.C. Penney’s with my cousin and younger brother. We then shot a ton of cars with paintball guns during a Fourth of July event. It was hilarious then, but the thought of me coming back from the park with my family on the Fourth of July and finding my car covered in dents and paint would totally tick me off.


#47 Brotherly Rivalry

When I was around twelve years old, I was sleeping in the same bedroom as my older brother. One day, my brother really got me angry (I don't remember why). That night, I decided to take my revenge on him and did something disgusting. When he fell asleep, I took one of his candy from his personal reserve, I did rub it in my butt and put it back where it was. Hopefully, he wasn't asleep and saw me doing it. I was ashamed for years when my family heard about it!


#48 A Better Ending

When I was 14, I had a short-lived relationship with a girl that was absolutely in love with me. The thing was, I really didn't love her back; I was just with her because the girl I actually liked rejected me and I needed a way to tell her that her rejection didn't affect me. I realized how dumb that was after a while and I just started being a jerk, acting disinterested and all that, so she would stop liking me and end the relationship in her own terms. We're friends nowadays.


#49 An Innocent Mistake

At graduation, my friends planned on holding my best friend on our shoulders while everyone threw their caps. We held him up and everyone threw their caps... and so did the friend who was holding his back. He took both hands off him and he fell off our shoulders, hitting his head on the concrete. We spent the next few seconds keeping him awake while the medics came over and helped. He ended up being fine a few minutes later. It was terrifying at the time but now we joke about it from time to time.


#50 Brothers For Life

I gave my best friend a concussion and a wicked scar across his face after we'd had a fight in school. I chased him into the bathroom and he tried to close the stall door, but as he was locking it, I full-on Sparta kicked it open. The thing crashed into his face, knocking him out cold and leaving a massive cut. Joke's on me though; that scar got him a lot more action than me as we got older. And he's still my best mate to this day. The scar has mostly faded too.


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