Reddit, what is your best teenage fuck-up story?

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41

When my brother and I were in our early teens, we didn’t really understand how important mail was, so we decided to steal all the mail from our neighborhood. For about two weeks straight, we would strap on our rollerblades and just go from mail box to mail box ripping up everyone’s mail. We even went as far as to put random notes and smashed up concrete into the mail boxes. Eventually some random lady saw us doing it and we bolted home and jumped in the pool, trying to pretend we were there the whole time. Almost all of our neighbors came over and took turns screaming at us. It turns out, as this was right after 9/11, we really freaked a lot of people out. Anyway, my mom called the cops on my brother and I and had them bring us to the police station to scare the crap out of us.

TL;DR Committed a federal offense at the ripe age of thirteen.

42

When I was in high school I had a girlfriend and we were seriously considering having sex for the first time. She started taking birth control so I knew in about a month I’d be losing my v-card. After a few weeks I started taking a condom whenever I’d go to see her, just in case.

One weekend we were going out to her parents campsite with some other friends (no adults) so I was sure this was going to be the night. I had one good condom a friend had given me, and one shitty one that you buy from restaurant bathrooms. I put them both in my front pocket with my cell phone (motoRokr).

I was taking my parents’ car so my mom was asking me the typical, “How late will you be? Who’s going to be there?” kind of stuff. She finally asked me if I had my cellphone and instinctively I went to pull it out of my pocket to show her.

When I pulled the phone out both condoms came with it and fell on the floor right between us. I can still remember the silence between my mom and I as we both looked down at my diverse condoms. I was losing my shit because I thought I’d blown my chance before it even happened. Finally she just looked at me, sighed, turned around and walked away. I scooped up my condoms yelled bye and ran out the door.

We’ve never talked about it, one day I’ll have to ask her what she was thinking at that moment. Oh, and if you were wondering, I didn’t even need the condoms that night, but that’s another story. :frowning:

43

Me and some friends decided to make a bomb…

I’ll explain : I was 13. Me and some friends watched a movie where we could see someone making a pipe-bomb. We thought that it was awesome, so we gathered the materials required. I took a “Cat food bottle” bottle, emptied it. (It was about a 8L bottle.)

I had a box full of fireworks under my bed, (A souvenir shop near my house closed, and they had a shit-ton of fireworks. My friends and I took gym bags and rushed to the shop. We carried every single fireworks that were in the trash. I told my friends that I’d take care of them, so I threw them under my bed. My parents never knew about this.

But anyway. We took about 50 fireworks, and opened them with a knife. I filled the 8L bottle with the black/gun powder. There was A LOT of it. We also needed sharpnel. We thought of adding nails, but one of my friend (the brighter one), thought that maybe it was a bad idea. I had a BB gun, so we filled the bottle with about 500 metal BB balls.

I lived near an open field, but there was a car dealer nearby, but we didn’t care. I placed the bomb, and placed a little nylon rope inside. It was about 5m long, so it would leave us time to get the fuck outta there. I armed the bomb, and we ran like we never ran before !

We were about 50 meters away, and we heard the loudest sound I’ve ever heard. Then, we heard the 500 BB metal balls hit some sort of metal. I looked at my 2 other friends in fear. We knew what just happened. Earlier in the story, I mentionned that we were near a car dealer. We slowly get up, and notice that the employees were outside, and a lot of the cars were pretty heavily damaged. They had scratches everywhere… It was a Subaru car dealer, and these cars are quite expensive.

We did the most logical thing ; Run like our lives were in danger. We ran for 10 minutes straight. Once we reached my house. We all agreed to never, ever, talk about it. No one else know this. I never made a bomb again.

PS : It took me 10 minutes to write this from my phone, ao there might be some gramatical errors, I don’t speak English fluently, so it might not be perfect !

44

In 2007, my father bought me a 1997 Ford Mustang for my first car. It was a 6-speed GT convertable. Was it brand new? No, but I loved it. Growing up I was nerdy kid who did not get into trouble. Before I got a car I’d much rather stay inside playing xbox than go outside. I didn’t start going to parties until I was 17. One weekend, my friends invited me to a house party in Big Pine Key. I lived in Marathon, which is about 20 miles away from Big Pine, so I could either: A-Drive to the party and worry about driving home drunk or B-Park my car somewhere and take the bus to Big Pine.

Because 17-year-old-me is such a genious, I decided to park my car infront of this sketchy bar called the Brass Monkey because it was located right next the bus stop. My buddy was coming along, so we rode the bus together. The rest of the night went well with no incidents. Good times were had, I got properly drunk, and made some great memories with my high school buddies. Unfortunately, the host of the party had to kick everyone out. Becuase my buddy and I took the bus, we had no way of getting back to our island. From 3:00am till about 6:00am we were stuck roaming Big Pine until the bus came to pick us up. From the bus, I noticed something was off about my car. Upon closer inspection I see that someone had slashed the convertable top to my car. Nothing from inside was stolen. I’m guessing some asshole form the bar must slashed it.

Now I’m stuck in an aweful situation. There was no way I was going to avoid my parents learning about my slashed top, but God have mercy on my soul if they ever found out I went to a party after lying to them about sleeping over a friend’s house. So I lied. I told them that my top was slashed while I was at my friend’s house. I had convince my friend’s parents not to tell my parents that I was lying. I had file a police report. The whole time my parents were skeptical because my friend lives in a very nice neighborhood. Replacing the top costed about $1,500. I’m currently 23 and my parents still have no idea.

TL;DR Lied to parents about weekend plans. Parked car at a bar. Convertable top was slashed. Convinced friend’s parents to cover my lie, despite police reports being filed.

Edit: 5 speed. I’m an idiot.

45

I smoked a crack rock in the middle of my 4th period class. Ended up in a detention center for a bit and proceeded to drop out of school.

Edit: I cleaned up nice and got my diploma through a Virtual learning program later on the next year.

46

Got drunk with my two best friends (guys) and proceeded to drive around the neighborhood, jumping over walls and going into people’s pools in our underwear. Got back to friends house, whom had a major crush on me, and I proceeded to have drunken sex with the other friend on his own bed while he spent the night on the couch. Worst part is that his friend went to ask him where the condoms were.

47

Walking down the street, I was 18. I guy I new from a different high school was parked along the local hangout on the cruise strip(midwest NE). He asked if I knew where to get any pot. Said no, BS’d with him a while and then walked on down the street. About a half block later another guy I knew I stopped and talked to. He asked if I knew anyone wanting some pot, I pointed down the street to the other guy. Said my goodbyes and walked down the street. Months later, 2 days before Christmas, cops knock on the door. Hand cuff me. I get charged with conspiracy to distribute the MJ and get sent to prison. Sat 15 months for a quarter ounce of weed I never saw or profited from. The guy who sold it sat 6 months. Yeah, I got to see dead bodies being carted out of cells(suicides I think), people getting punked and the lovely experience of having to sit in rooms with child molesters all for a quarter ounce of pot I never saw. Funny thing is, if I had a family I wouldn’t of served more than a week. This was 20 years ago and I still have a felony on my record. No kid should go through that shit over weed. I know mine wouldn’t.

48

Got caught with a container of weed at school. It wasn’t mine, I was holding it for friend.

I got caught because I was taking double lunches- the teacher in the class I took during 2nd lunch had kicked me out.

In hindsight, I could have probably got the teacher in trouble for kicking me out, as I’m pretty sure she wasn’t following protocol. I had even approached the school counselor about what the teacher did, and all he gave me was this cryptic answer like “there’s a way to get out of this, but I can’t tell you”

In hindsight, South Tucson was a ghetto-ass place to grow up in.

49

Kind of a fuck up story…
I use to work at Chuck E Cheese and decided I didnt wanna work there anymore. Instead of quitting professionally I decided it would be better to quietly sneak out the back door with out telling anyone. Oh, I was the only cook on that night and it was right before the dinner and party rush on a Saturday night. Needless to say shit got fucked up. Parties were eating their cake before their pizzas, orders took forever to come out, and general chaos ensued as it took a while for anyone to realize I was M.I.A. I feel kinda of bad about it now but at the time I was just being a stupid kid.

50

I have two:

First, a girlfriend got some stuff back from her ex. He destroyed it all before giving it to her. So we decided to take everything of his, put it in a box and burn it. Since we were in high school, at a summer band practice, we went to the greenhouse area behind the school where people smoked pot. Unfortunately the hordiculture (spelling?) teacher saw the smoke and came over. We ended up having the choice between suspension for the first week of school or working at the school to help set it up for the start of school. The teacher tried to get us arrested for arson and explosives (claimed the wire from the fake roses were fuses)

Second. Girlfriend and I were having sex in her car in broad daylight at a shut down factory her grandfather used to own. Her dad went to illegally use the dumpster there and caught us. Didn’t know he was there until he hit the car with a 2x4.

Same girl in both stories. Been together for almost 10 years now, married for 3.

51

I was caught by security with two liters of vodka at the holiest place in the Jewish religion.

52

Well, I was bored one day in elementary school and decided watching porn would be a good way to spend music class. This was before smartphones and 3g internet, so I used the shitty, expensive pay-per-minute connection that my phone had. Youporn was buffering very slowly and the format was obviously not made for phones, so eventually I got tired of it and gave up.
Later that day, and the following 2 months for that matter, I got a message saying “enjoy the service”, followed by a link to youporn.

My dad was not happy to learn he owed youporn, more specifically the “big boobs” section just under 300€.

53

The summer I was 17, I was smoking pot with some friends when my mom called my cell phone and told me I needed to pick my little sister (she was 8 at the time) up from a birthday party that was being held at a park in the next town over. I got in the car and drove to the park, paranoid that I’d get pulled over and the cops would know I was high. By the time I got to the park, I was so relieved that I accidentally hit the gas instead of the brake as I pulled into my parking spot. The parking lot wasn’t paved, just a big gravel lot with big logs set up to form rows that people could park in front of. So when I hit the gas, the front of my car rolled right up onto this huge log, and both my front tires were hanging a couple inches off the ground.

I got out of the car and tried to push the front of the car off the log, but it wasn’t moving at all, so I decided the only solution was to go get my 8 year old sister and make her help me push the car. So I did that, and sat trying to reverse the car while she pushed. Nothing happened. Obviously my sister was too small to push the car on her own. I decided the best thing to try would be for both of us to push the car, while I had it sitting in reverse, with the driver side door open, and for me to jump in as soon as the car started rolling. Excellent plan, right? (I was high.)

This plan worked like a charm. The car rolled down off the log and… kept on rolling across the parking lot. I ran after it, trying to hop back inside so I could stop it, but it was already going too fast for me to risk jumping inside. I could only watch, stoned and horrified, as my car rolled across the parking lot without me… right into someone else’s parked car.

Not my greatest moment.

54

I went into The sewers with my friends and got attacked by a mentally challenged man that lived down there.

55

I used to hang out in this friend group of generally fucked up kids. They all started drinking and smoking when they were in middle school and a bunch of them continued to get into harder and harder stuff throughout high school. This one kid, lets call him Ralph, was the biggest fuck up that i know to this date. His mom died when he was 5 or 6 and his dad was in jail so he lived with his cousin’s parents. He pretty much ruined the reputation of my good friend Sam (not real name) by telling everyone in the school that he skinned squirrels for fun and had sex with his little brother. Despite this, Sam kept hanging out with Ralph because he had zero friends at this time (I did not know Sam at this point). One day, Sam smokes up Ralph and as they are about to part ways, Ralph pulls a knife on Sam and tries to rob him of the rest of his nugs. He presses the knife up against his chest and draws some blood but Sam tells him to fuck off. Luckily, Ralph just sprints away and doesn’t stab the shit out of him. A few months later, Ralph steals 300 dollars from this girl’s parents, goes into the city and spends all of it on crack, morphine, and pizza. He then steals another 200 dollars from another girl in my high school shortly after and spends most of it on ketamine. He pretty much fucked over anyone who had any trust or hope in him and now everyone hates him. He dropped out of high school during his senior year and moved to Arizona with this guy who claims to be his father.

56

I popped my left front tire on my ford escort trying to drift on snow. I hit the curb that was on the inside of the turn. My dad wasn’t pleased

57

When I was somewhere in my teens, it was the middle of Summer in a small-ish rural town, probably 10,000 people total.

So, I was at a family reunion and we were allowed to bring friends, so there was something like 500 people from all over the country (And even some from Britain) and we all partied hard for like two weeks, at my house.

Anyways, I was drunk with like ten other people and may or may not have been smoking pot in the garage. We also found Phallic Symbol humor hilarious, especially combined with full nudity.

So, we screwed around with a chainsaw, and it ended up getting sat down, tip-up. One of us tripped, hit one of those metal shelves which proceeded to fall down, I back up, tripped, and landed ass-first onto a chainsaw. It went about two inches in.

I thought nothing of it, in fact, it was hilarious.

So, bedtime comes around about twelve hours later, and we still have tons of people up, like around fifty of us have not left for a motel or anything. It was around 3:00 AM, and I felt a horrific pain in my asshole and bowels, so, I excused myself to the restroom, and just as my ass cheeks hit the toilet seat, all hell broke loose, it was red diarrhea exploding from my butthole accompanied with a horrifying pain in my ass, I screamed, so loudly it probably got the attention of everybody in the house. I heard a knocking on the door, and I was like “ohhh shit” I said “Don’t come in!” just as another volley of bloody liquid stool exploded from my bowels. Then, the door broke down, I was covered in bloody shit, and I was like “I’m fine, jeez.” I stood up, pulled up my pants, everybody laughing their sides out. As I stepped out of the bathroom, I felt a portal to the fiery depths of the tenth pit of hell open in my ass, I screamed, and more bloody shit exploded from my ass, and then everything went dark.

I woke up in the hospital, and the doctors said that I had surgery, and was out for twenty-four hours. They slapped me in a wheelchair after taking my vitals and letting my wait in there for a few boring hours. My next few poops were hard and hurt a little bit, but weren’t bad. Then suddenly, I’m watching TV, and a really awful pain happens in my butthole, and BOOM! A solid, bloody shit about a foot long and around four inches thick slides out of my anus. I was sent back to the hospital, and they said that was expected, and gave me another surgery. For around six months after it wasn’t that bloody or painful, and a little soft, and then it was fine, but I still feel a tiny cramp, which is fine, or, so the Doctors said.

TL;DR: Don’t mess around with power tools while drunk and high.

58

Got home very drunk on NYE, I thought I lost my keys, so I rang the doorbell. The keys were in my pocket. I had previously fallen asleep in the subway and traveled the whole city twice while sleep (I did the math).

59

When I was 15 I started going for this girl I really liked. I chased her for about two years, there were other girls in between obviously but I never really stopped liking this girl.
Anyway finally we ended up going out for a bit and I spoiled her something awful, I was head over heels, young love and all that.
So we went out for like three months before she cheated on me with one of my best friends then trailed me along for another few months until her and my former friend got more serious.
I’d had issues with depression before but after that I went very downhill. I started having anxiety issues and my depression only got worse, and I thought about suicide often. I’ve gotten better since then but I’d say that my time around that girl is my biggest teenage fuck-up because it almost killed me.

60

I destroyed my step-father’s wheelbarrel.

As a smart 13 year old boy is, I conjured the idea of a toilet bomb. Basically how it works is that you get toilet cleaner and aluminum foil, then you put them inside of a bottle or container and tightly close the lid. It is similar to how a dry ice bomb works but it is much less powerful. I got my two brothers to help me, A (who was 14) and E (my twin brother). I brought over the said wheelbarrel and set it up so we could hide behind it when the bomb went off. Needless to say, after we set up the bomb, we were all giggles and laughs while it was growing in size. What we had not anticipated though was that it would rocket at us. The lid blew off and the stand that we set it on tipped towards us. The projectile hit the wheelbarrel’s wooden structure (right above our heads) and tore it off. This rocket was still going and hit my neighbors porch, where it proceeded to explode and break her glass sliding door. Tl;Dr: I had incurred a broken glass sliding door, a massively dented and torn apart wheelbarrel, and a metric butt-ton of shit in my pants.