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Painful Regrets: The Dark Memories People Wish They Could Change

Jamie Hayes

We all have those painful memories that never leave the back of our minds. The dark moments we wish we could take back, but we can’t. Don’t worry—we are not alone. Whether it’s a forbidden affair, a cruel word said in anger, or a life-changing mistake, these stories prove that some regrets can haunt people forever.


1. Spit It Out

I had just come back from playing soccer (I was 12 years old) and was severely thirsty. I saw a glass of what I thought was sweet tea on the kitchen counter and immediately tried to gulp it down. In an instant, I realized I’d made a horrible mistake. It turned out to be my father’s glass of dip spit. For those that do not know, that is the spit that people who chew tobacco make as a byproduct of the process.

I threw up all over the kitchen counter and floor and they found me there a few minutes later dry heaving in the fetal position. I’ve never been able to even smell Copenhagen without gagging to this day and I am 26.

insanitynow08

2. The Corn Holder

I thought it would be a great practical joke to bury a corn holder—small handle with two sharp prongs to hold corn on the cob—pointy side up in my yard and wait for someone to step on it. Of course, being a kid after all, I lost interest after a time and forgot. Sometime later in the summer, while walking barefoot, yes, I stepped on it. Man, that hurt. Learned a valuable lesson about practical jokes.

phil8248

3. Life Is Totally Unpredictable

I ended it with my boyfriend because of school. We planned on getting back together after he was done with school, and I planned on talking to him during summer break. I never saw him or spoke to him again, though, because he died just before the semester ended. 12 years of friendship, eight years of dating. It seemed like a good decision, and I missed him, but we were doing pretty well. And then I got a call from one of our mutual friends. He told me to sit down, and he gave me the heartbreaking news.

It might have been the right decision at the time, but I regret not calling him, texting him, telling him the whole thing was stupid and that I missed him too much during those nine months before he died.

parrottrolley

4. Search History

I was 12 years old and tried searching everywhere for X-rated material of children of my age because I didn’t like looking at adults. Boy, was I stupid.

brokenindu

5. Never Pulling a Stunt Like That Again

When I worked as a stunt performer, my last performance was with a particular stunt group. They wanted me to do a particularly dangerous version of a stunt that I already didn’t love, so I felt pretty uncomfortable. I had done the regular version thousands of times and could practically do it in my sleep, but this new version worried me.

I agreed to do it because it was just gonna be the one time. What were the odds of getting hurt doing it just the one time, I thought! Later that day, I found myself in a second hospital after being airlifted from the first one because my injuries were too severe for them to handle. I had literally a gallon’s worth of blood transfusions (they weighed me before and after), and a life-saving surgery.

If you have a bad feeling about something, take it seriously.

WTF_HomeSlice

6. Hold Your Tongue

I told a friend with a speech impediment to stop stuttering. I felt horrible the second it left my mouth—but it was too late. The look on his face broke my heart.

JakeBit

7. It Takes One to Tango

As a teenager, after watching a cop show about a kidnapping, I got really curious about what it would be like to be tied up. With some flexibility and creativity, I managed to get myself gagged and pretty securely bound to a kitchen chair. I could still get loose but not without some wiggling. My mom came home early, and I couldn’t get loose in time.

She FREAKED, thinking I had been robbed. Then, when she untied me, I explained, she thought I was a freak.

brianoops

8. The Pyromaniacs

When I was 11 years old, my friend and I soaked a tennis ball in gasoline and lit it on fire. We put gloves on and tossed it around with another friend. Just cus. We ended up throwing it to him in an arc and he missed the catch; it slid down his chest, leaving a fire gasoline trail on his shirt. He had 1st-degree burns and we really got in trouble for that one.

TriscuitCracker

9. Sorry, Mom

I was sexting my gf one day and my mom had texted during that process and I ended up replying to her message instead of my gf. I still get laughed at for it and it’s been about 10 years. Yep, I told my mom I wanted her to sit on my face.

positivecontext

10. Thank You, Facebook Robot

I was sending an adult video link to my girlfriend and accidentally shared it to my facebook wall instead of in a message. I don’t know how, I must have been tired or drunk or something. We’re talking some pretty shady stuff. I didn’t even realize I’d done it until the following day.

I woke up to a message from Facebook telling me they’d auto-removed my post because it appeared to be spam (the message contained a link and my heart almost jumped out of my chest and ran away). I don’t think anybody saw it, thank god. I’ve never been so grateful to a robot in my entire life.

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11. Runaway Driver

I was working on one of those TV shows where you do stupid things in public and film people’s reactions. In the skit we were doing, a man would be jogging with a stroller containing a life-like baby doll, and I was going to hit him with a car. The jogger was wearing bright green—they dress funny on these shows so that you don’t mix up the cast with pedestrians. So, I’m cruising up to the stop sign in a beat-up old ford, my adrenaline is really pumping.

This was my first time actually being involved in a skit. I see the bright green jumpsuit, and I rev it—but when I realized what was happening it was too late. I hit the wrong guy. It was just some dude jogging with his kid. I realized what happened when the guy I hit didn’t jump onto the hood the way you’re supposed to in these stunts. I honestly don’t remember anything about the incident after that, I was in shock. The dad had a few broken bones, the baby was fine.

Needless to say, there was a huge settlement paid out. I’m currently pursuing an unrelated career.

ranoverbaby

12. You’ll Always Wonder What If…

It all hit me when my ex died in a car accident. We were married for almost six years. I was so young, had no idea what I was doing. I wanted a divorce and can’t even remember why. Our son was seven. Now he’s 18. He was the kind of man that was good at everything and a very hard worker. A man’s man and a family man.

Before he died, we were talking about getting back together. He was my best friend.

bipolarfun

13. A Child Mourns

My mother passed away when I was eight years old. Cancer. It came to the point where death was inevitable. My dad asked if I wanted to see her and I said no.

Telestrial

14. First Time is the Worst Time

In high school, I was on the verge of losing my virginity to my girlfriend of two years who also happened to be my neighbor. The scene was set perfectly, both my parents were gone (dad was out of town and mom was working until nine) and I had just asked her to prom that day… So things are getting hot and heavy, and all of a sudden I hear a noise downstairs, but assume it’s one of my cats wreaking havoc as usual. We kept going—totally unaware we were heading for complete disaster.

About a minute later my (extremely conservative) mom walks in, and as the door opens she lets out a faint scream and runs downstairs. BUSTED. Now while this moment was awful enough, after going downstairs to face my mother who had immediately called my (also very conservative) dad, she goes on a rant about how irresponsible I am and how protection doesn’t always work, and I’m proof of that.

So that’s the story of how my relationship was ruined (just got really awkward after that) and I found out I was an accident. Maybe the act itself isn’t anywhere near as embarrassing as some of the ones on here, but I swear the situation made it mortifying.

bluezfawkx

15. Dark Date

I met a guy at the skate park when I was 14. He asked if I’d go out with him the next day. I thought he was gorgeous, and when he said I should dress up I expected something special. The next day I showed up, and I couldn’t believe my eyes. He took me to his little sister’s funeral.

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16. The Backstabber

In seventh 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. I had no idea what I was doing was so cruel.

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.

alikatbar

17. Lost In Translation

When I was, maybe 14 years old, my family and I went on vacation to the Dominican Republic. First, let it be known that place is awesome. Such a good time. What I was unaware of though, was that it was also a huge European vacation destination. Well a day or two goes by and I’m pretty bored. All I’ve done is spend time with my family, and of course, normal 14-year-old me knows vacations aren’t meant to be spent with the family!

Finally, I see a group of English children who look to be about my age playing soccer (football) on this field within the resort. Well, genius me decides these kids are not going to like me unless I’m English. So what do I do? I decide, by god, I’m going to become English and hang out with these guys. So I approach them and it actually goes a lot better than I thought.

I end up spending most of my time hanging out playing football with these chaps. It was awesome, I legit had these kids thinking I was English, they introduced me to their (topless) sisters and mums, and I genuinely liked these people. Unfortunately, I held a dark secret that finally surfaced on the second to last day.

Pretty normal day, we’re all hanging out playing ping pong, everybody’s shouting having a good time, I’m shouting, of course in my English accent, when all of a sudden my WHOLE American family shows up behind me asking what I was doing…in front of all my new friends…..and their topless mums and sisters. Ugh, I have never felt more shame EVER…

Just seeing ALL those looks of confusion and disappointment (and of course pure laughter from my dad and sister). To this day I still haven’t lived that incident down. Eight years and they still give me heck…Make sure your American family isn’t standing behind you while you lie to a bunch of English people…about being English…

iAMtheBelvedere

18. Caught in a Compromising Position

My Dad walked in on me squatting over the business end of a hairdryer. I’d not long got out the shower and wanted to blast my gooch with warms. So there I was, naked, with my back to my bedroom door, hovering over the hairdryer. I didn’t hear Dad walk in due to the hairdryer. He just yelled “BUSTED!” and walked out.

Mikchi

19. MIA: Missing in the Air

Not a pilot—but was an air traffic controller. I have a million screwed-up pilot stories, though. One very sad story was a pilot who flew in on “emergency fuel” in his MiG he flew around to air shows. He was erratic and didn’t listen to instructions well, but landed safely. He left my airport a few days later…to this day, I regret not stopping him. He ended up going down in the mountains and was never found.

The finding was: Likely low fuel due to scraping his fuel tanks at an air show prior to arriving at my airport. He never even had it looked at while he was at my airport. He was aware he had scraped his fuel tanks, he came into my airport using emergency fuel, yet he pressed on after that, to his death. The truth is, pilots are just people. They’re flawed like the rest of us.

internetownboy

20. Moments of Weakness

I yelled at my grandma for complaining about something—I don’t remember what it was, something stupid—because I was tired and it was cold and after midnight on a day I had to wake up early to go teach kindergarten and she was sick. I woke up 2 hours early to my mother crying so hard I could hear her across the house.

My grandmother died about 2 hours after I yelled at her. I still haven’t forgiven myself for it and I’m not sure I ever will.

InsaneChihuahua

21. Exploding Beers

My parents used to host a lot of parties when I was at the most dangerous age (young teens) for boys. There’d always be a bunch of leftover beer, and my parents refused to drink anything that wasn’t their brand, so they’d throw it away. Instead, I’d invite my friends over, and at the end of the night, we’d take all the leftover non-Bud-Light beer, put the cans on the road, and hide in the woods. Cars would run over them and they’d explode.

We stopped after the time our dumb prank almost got us killed. A guy hit some, stopped in the middle of the road, got out of his truck with a huge shotgun, and chased us into the woods for about ten minutes.

Hardcore_EHS

22. The Poop Scoop

I was pretty young when this happened, maybe 13 years old. I was in a hot tub with my friends and I thought I had to pass gas…unfortunately for me, I was wrong. Pooped in my bathing suit, so I casually grabbed it with my hand and while no one was looking, I dropped it behind the hot tub.

SaiyanPrincess19

23. Leader of the Gang

I did a lot of regrettable stuff, to be honest. I think the biggest were my fights with my brother. We used to fight with screwdrivers and knives, and we both still have visible scars from some of the fights. We’ve choked each other out several times and just generally always escalated our fights beyond the reasonable for siblings.

I used to also have a small “gang” of kids younger than me. To adults, I was simply the mature kid most of them trusted to watch the kids, and generally, I did. But I also did terrible things that they never knew about. I had them fight each other for my entertainment, steal things from small stores nearby, dumpster dive for treasures for me and fight other kids not in the “gang.” They all generally listened to me completely without question and also genuinely loved the chaos and violence they could have while I pretended to be a mature figure.

There was some silly stuff too. My brother and I, when we were really young, would “recreate” the crucifixion of Jesus Christ with each other. One of us would play Jesus and strip to a towel and the other would help pose them on two long pillows shaped into a cross before pulling them off and putting them into a cave of pillows where the Jesus was to dress within and emerge from “reborn.” Freaking weird.

Disposable_alkaline

24. That’s Why Pencils Have Erasers

When I was six years old, I once stuck my little finger into a pencil sharpener and twisted it around a few times like it was a pencil.

I nearly passed out.

SmallCitron

25. Brotherly Love

I helped my older brother steal my mom’s pain medication as a really young kid without realizing the significance or really meaning of what I was doing. He convinced me it was all an elaborate game of cat and mouse we were playing. I didn’t know he was an addict or even what an addict was. Honestly, I was just ecstatic that the older brother who I looked up to and idolized, as many young boys do—who usually abused me and was being nice to me—thought I was helpful and useful.

I’ll never forget the time when I was nine years old and my parents went out to dinner for their anniversary. They left my older brother to watch me at home. Long story short, he had me climb up on the counter and hold the door on the triple padlocked medicine cabinet in place, so the locks didn’t bend while he unscrewed the hinges and reached in to grab the bottles of pain medication he wanted.

He stole a handful out of each, put them back, and screwed the door back on. He was super nice to me and was giving me all sorts of positive attention. He went to his room but promised he’d be back in a few minutes. He said we’d sit down together and he’d play my favorite video game with me. I was super excited because I felt like I had made him proud, and I eagerly looked forward to gaming—but I was about to have my heart broken.

He never came out of his room, and I waited for about 45 minutes. I eventually gave up hope that he was coming when my parents came in the door. They were all happy and giddy from a nice dinner and drinks. All it took was one look at the cabinet and my mom knew he’d broken in. She sat me down at the kitchen table and explained what him getting into that cabinet meant and why he wanted in.

She asked me to tell her if I had heard anything while they were gone, and it just washed over me all in an instant that my brother had just used me, and couldn’t care less about me. I broke down crying and told her everything about breaking into the cabinet and all the other ways he got me to help him. I begged her not to give me to the old guy who liked little boys, as my older brother convinced me she would if she ever caught us to ensure I’d stay quiet.

The look on her face was haunting when she heard me say that. She asked where I got that idea, so I explained and she was mortified—but she assured me I was safe and she would never get rid of me, especially in such a horrible way. She told me to go to my room and listen to my Nickelback CD I had recently gotten.

I had the music on full blast, but it didn’t stop me from hearing the screaming. My mom decided that his presence was no longer safe for me and that she would send him to my biological father across the country. Before he left, he wrote me a note saying how he hated me, how I was worthless, and how I’d broken up the family. It still haunts me to this day.

dman2316

26. A Dangerous Game

My cousin and I were like 7ish or so, and playing upstairs in a room by ourselves. My aunt left her sewing machine in there ready to go. We were fascinated by how fast the needle moved up and down when we stepped on the foot pedal. Then we had the idea to see who could get their finger out of the way before the needle started moving.

He went. Safe. I went. Safe. He went. Blood shot out and screaming commenced.

DaShMa_

27. The Silver Quarters

My dad has a massive collection of silver quarters he inherited from his dad. At one point, he counted and put them all in paper rolls. My younger brother took a few rolls, having no idea what they were or what they were worth, and blew all of them in freaking quarter machines. My dad was beyond angry. Why he kept them in a cardboard box in a closet, I don’t know.

Either way, my brother shouldn’t have been going through their stuff and taken them. My dad keeps them locked up now.

TangoHotel04

28. The Pet Poop

I took a dump in a plastic bag and hid it in my closet for…reasons. My parents had to have found it. I went to check on my pet poop one day and it was no longer there. We never spoke of it. They’ve both passed so I will never know who found it or what happened to it. Life’s mysteries. Also, used to stick my wang out between the curtains of my bedroom window after bedtime when I first started getting boners because the risk of being seen was thrilling (I lived on a busy street).

Guess I was a born exhibitionist.

FastWalkingShortGuy

29. The Arsonist

In eighth grade, in the fall season, my friends and I were hanging out in this tunnel. It was filled with dry leaves. As we sat on the walls of the tunnel goofing off, I was mindlessly throwing matches into the leaves. I had this weird obsession with fire since I was really young. I was spacing out just staring at the little flames until my friend grabbed me and pointed out how fast it was spreading.

We started stomping on the leaves and the fire just kept rapidly spreading. We looked at the openings of the tunnel and black smoke was just pluming out of both ends. A few other things happened after that but it ended with my friends and I running away. The way our neighborhood worked, we could see the tunnel from my friend’s house without being seen by anyone else.

The tunnel had a massive flame coming out of both ends. I can’t believe how bad the fire was. But it was in a remote area, there wasn’t anything close to it that it could burn down. Not justifying what I did, because it was extremely reckless, dangerous and destructive. But all things considered, it was pretty harmless and luckily, I never got caught.

rosecolour

30. Youthful Take-Backs

Hanging out with a friend instead of visiting my father in the hospital. He died that night and I never got to say goodbye.

PepperoniQuattro

31. The Nice Car

When I was 14 years old, I was at my friend’s house. His dad had a really nice late 60s early 70s Chevelle (I think). My friend and I were sitting there looking at it and talking about it. Being at that age when cars just seemed so cool, I wanted to see the engine. We popped the hood and looked for a while and then slammed the hood and moved on. We had no idea the terrible mistake we’d made.

The hood didn’t latch properly, and the next time he drove it the hood flew up and he crashed the car. It was a 30+-year-old car at the time and a complete timepiece. His dad was going through a divorce at the time because his mom cheated on him. So, this guy was just trying to enjoy his nice classic car after his wife cheated on him and it got destroyed.

I still feel freaking terrible about it.

SeeYouOn16

32. The Predatory Poop

I was at some Amway function at a lake with my parents, I couldn’t have been more than 11 years old. I had to poop and didn’t know where the bathrooms were, so I swam out a little way and pooped. A few minutes later, the tide brought my solidly formed log floating towards the gaggle of us kiddos resulting in many screams and frantic splashing as they tried to escape my predatory poop.

mseuro

33. Burn Victim

I played poker with a guy who was nicer than nice, such a great guy. He only came once and never saw him again. His face was near melted off. Face melted into chin, little face structure. Barely a nose. As a kid, he was doing dumb things as kids do, and was playing with gasoline and matches. For the rest of his life, he almost never came out of his home.

Nice guy, but apparently his one or two social events every few months was all he could handle mentally; from what we heard from people who knew him better than us. We were very welcoming and asked him to come back but he said no and ghosted us. Felt bad for the guy. All kids do stupid stuff. He had to pay for it the rest of his life.

Toucansamual

34. Teenage Angst

I remember when the housing crash happened in ’07 and it hit our family hard. My dad worked as a specialist carpenter doing really convoluted stair systems and fancy trim/crown molding. Needless to say, there wasn’t any demand for high-end, custom homes during that time when the banks clamped down on mortgages. I was just starting my angry, hormonal teenage years, and I was such a jerk to my parents because we couldn’t go out to eat as much or go on week-long vacations every year.

Now I need to say that we weren’t spoiled; I grew up on a farm and spent a lot of time helping out for most of childhood, so we did “work” for some of the nicer things we would get. My dad was also the only source of income and while we never were rich, we were solidly middle class. I still feel awful for some of things I said. I sounded like a snobby brat.

It hurts even more because I found out my parents had to take a loan out against their house to keep us all afloat because my dad couldn’t find enough work. They’re perfectly good now, though. If you’re younger and still living with your parents; be mindful of the things you say or ask for. They may be under a lot of stress that you don’t see.

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35. The Thief

I stole someone’s Gameboy game because a friend told me to. In fourth grade or so, I was attending a summer program (for kids who were smart and got good grades in school; remember this) where you could take special classes to learn stuff you normally didn’t in school. Medieval history, other languages, building stuff with Legos, film/TV production, etc.

I was in a photography class that year and rode on a bus to the program from 20 miles away. A friend on the bus convinced me to start stealing from the other kids in class. Stupid stuff at first, but then he asked me to steal someone’s Pokémon Blue game (this was in the late 90s when this game was HUGE).

This time, the teacher got involved and there was a massive search for it. That should have been the moment I “found” it and was the hero, but no…the stupid kid me decided I wasn’t going to get caught. Then the teacher started pulling kids aside to talk, one by one, and I knew I was doomed. He got to me, but somehow I convinced him that I couldn’t have possibly stolen the game because my mother was going to take me out to buy it that very day! Somehow, I got away with it and delivered my booty to the bus friend.

I actually wound up going to middle school with him and ran into him in seventh grade, and asked if he still had the game. He did and offered it to me because he no longer played it. I still have it, and every time I see it, I feel bad about the kid I stole it from.

jordanjay29

36. Live in the Slow Lane

The day my dad killed himself, I was walking out of the house and running late for class. He asked me to have some breakfast with him but I just yelled out, “I don’t have time,” and walked out.

Nervousnedflanders

37. Southern Living

When I was in first to fourth grade, we lived in a real rural area of Georgia. I’m talking three miles down a dirt road, and 15 of the 17 acres of land we had consisted of swamp. For Christmas, I got a BB gun. Got taught all the gun safety stuff, was a good boy and listened. We were allowed to shoot cans, no bottles. Pretty simple.

Well, after a year of becoming highly efficient snipers of Busch beer cans, we needed more out of life. While exploring in the woods we would come across clay jars from time to time. We decided since they weren’t glass, or belonged to my parents, it was fair game. We used Indian artifacts as target practice. No, I had no idea what they were at the time. It was many years later when I remembered it, that it dawned on me.

I saw a lot of weird stuff in that swamp, but I did have another completely naive moment that I just remembered. This was ‘89-’93 time period, Deep South. I remember how silly I thought it was that grown men would dress up as ghosts, ride horses and have torches. I thought it was some weird re-enactment thing. Also, there were no black people out there so I didn’t witness any crime. Most likely some rally type stuff.

It’s amazing how clueless/innocent you can be at that age.

JoshuaS904

38. Grief is a Bad Dream You Can’t Wake Up From

Three years ago my father passed away. In the months leading up to his death, he had been struggling with idiopathic pulmonary fibrosis—his lungs were turning to scar tissue and no one knew why—and had been working with Duke Medical Center exploring the possibility of a lung transplant. He had just returned home from a multi-day battery of tests and examinations there and was feeling pretty good about his chances when he fell ill with what appeared to be pneumonia and was hospitalized.

He was having difficulty breathing (well, more than usual) so he was put on a ventilator. Very late the previous night I had returned to my own home, about an hour from the hospital, after a long car trip and was still tired from the journey when I received a call from my mother explaining the situation. We agreed I’d visit the next day when they had more information on his condition and he’d had a chance to settle in.

That evening his doctors decided to put him into (what was meant to be) a temporary drug-induced coma; he was fighting the ventilator and in a lot of pain, and putting him under would give his body a chance to rest and hopefully heal as the machine did his breathing for him. A few days later he was airlifted from the local hospital back to Duke Medical, where he was reevaluated as a transplant candidate.

His application was rejected because his condition had deteriorated so far that the transplant board didn’t believe he’d be able to survive the procedure or the months of rehabilitation that would follow. We made the decision to put him out of his misery and take him off life support, and my mother and brother and I watched him pass away.

Our decision ended up being validated by how quickly his body gave out; it took less than five minutes for him to go. The staff didn’t even have time to bring us snacks. Did you know that hospitals provide cookies, crackers, soda, etc. to the families of patients waiting to die? I didn’t. We thought it was kind of funny, even at the time, but the nurses explained it usually took hours for someone to pass on after life support was shut off, and those waiting usually got hungry.

Two things bothered me about the manner of his passing. One was personal. I strive to live a life free of regrets—but this is still the one thing in life I wish I could change. I didn’t make the effort to go visit him the day he was hospitalized. I hadn’t known it at the time, of course—no one did—but it would have been my last chance to speak to him.

The second was a sort of outrage on his behalf: he had been full of hope about getting his disease permanently managed and returning to some semblance of a normal life, but he got sick; then he was put under with the assurance it was just temporary, and he’d be woken back up in a few days—I took lots of pictures of him getting wheeled out and loaded into the chopper, to show him the adventure he’d been on without knowing once he woke back up—but he never woke back up.

It hurt that I didn’t get to say goodbye, but that wasn’t even the most painful part. What hurt the most was that he didn’t get to say his goodbyes, to anyone. It took me a long time to get over that. That night, after his body was taken away for cremation, my now-smaller family returned to our nearby hotel suite and I slept on the sofa in the main room, letting my mother and younger brother take the bed.

In my dreams—and I rarely dream—there had been some kind of mistake; my father came to the door of our hotel room and laughed at how inept the hospital had been, mixing him up with someone else, now go help your mother pack so we can go home. I woke up and stared at the ceiling of the hotel room and everything felt wrong for a while until I was able to sort out the difference between dream and reality once more.

TrekkieTechie

39. My Brother’s Keeper

I used to pee on my brother’s bed in the mornings, so I would get the first crack at video games or TV while he helped clean up “his mess.” I did not pee on my brother, I used to make sure that I was peeing away from him and on top of the covers. This occurred just a couple of times, probably coinciding with some video game we rented for the weekend.

I’m sure my parents were aware something was off about the whole thing but they never let on and now don’t recall being suspicious of me. I’ve told the story to my family and we laugh about it now. My brother doesn’t recall wetting the bed at that age. I am sorry for what I did, it was selfish action…but watching him “play video games wrong” was very frustrating as a kid.

seatoc

40. Boys Will be Boys

Oh, jeez where to begin. Here’s a couple. I once convinced my brother to jump from the second-story window under the pretense of, “You’re wearing basketball shoes you’ll bounce back up.” We had just seen the movie Flubber and thought this was what would happen. Didn’t get a chance to find out…because he landed through the soft top of our mom’s car.

We also took a sled off the peak of our house. Smacked into our neighbor’s house. He had to have reconstructive surgery on his cheek and I broke my nose on the back of his head upon impact. We didn’t understand the physics of bungee jumping and attempted it off our balcony with just a chain. He dislocated his hip while my anchor didn’t hold and I hit the ground.

I honestly don’t know how we’re alive. Combination of poor parenting and lack of fear/stupidity.

averagesizefries

41. The Vandals

When I was a kid, there were some woods behind our neighborhood that my friends and I loved to play in. One year when we were 13 years old, they were cut down to put in a new neighborhood and we were angry. Once the new McMansions started going up, we would go in and try to sabotage whatever we could. We’d toss entire pallets of drywall from the top floors, rappel down the sides of the houses with coax cable, brake duct pieces and windows, pee all over the place, move ladders and other equipment to distant places.

This went on for months, and I have no idea how we weren’t caught, but I remember that I told them we should stop when I heard the vandalism mentioned on the local news.

IWasSayingBoourner

42. Sudden Change of Heart

In this case, my ex was the one who had the regrets, but I love telling this story. I got dumped by text by this girl who I’d really, really liked for about a year. We were dating for a while when she decided to end it via text with no explanation at all, although I found out the next day she was seeing her ex all the time we were dating. Don’t worry though—the joke’s on her!

A month after that, I won the lottery. Never seen someone backtrack as quickly. Told her to get lost.

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Regret Breaking Up Facts

43. The Field of Fire

We used to hang out in this wooded spot on the outskirts of our neighborhood. We took an old couch there one summer to sit on. We proceeded to light the couch on fire and the flames got really big. Some trees also caught fire and a giant field burned down. We never said a word to anybody else because the fire contained itself, but it was pretty darn scary for a group of idiot 13-year-olds.

We left before the fire department came.

HollywooDcizzle

44. Baby Bird

This one summer I was somewhere around six years old and playing in the front yard. I stumbled upon a baby bird that had got itself stuck in a crack in between the grass and sidewalk. I loved all animals and was determined to get the bird out and save its life. I had to do it without touching the bird because I heard the momma wouldn’t take it back with human scent, so I went looking for something long to push it out.

I ended up finding a fireplace poker in the garage and stabbed it through the baby bird successfully freeing it from the sidewalk crack. My mom had been doing something in the backyard and I proudly ran over to her with this still alive and frantically chirping impaled bird telling her I saved it and not understanding why she is yelling at me to put it down.

Probably one of the earliest memories I can still vividly remember, besides the one time I pooped myself inside the Mcdonald’s play place and tried to hide it by smearing my logs around without it being noticed.

ComplexComposure

45. The Car Game

We threw a ton of stuff at cars. It was something that my entire neighborhood did. It was passed down from older kids to us, and then to our younger siblings. “You want to go car bombing tonight?” We’d go raid a couple of gardens and go to the field that overlooks Route 7 and have us some fun. I’ve thrown eggs, tomatoes, squash, zucchini, and even the occasional potato.

The fun was when people chased us. If you knew the town, you knew where it was raining from and you could pull in behind us. You would see the headlights light up the field behind us and then we’d have to run. When the people left their cars, we would split up and make them run. We were complete idiots. It wasn’t just teenage boys either. The occasional girl joined in the chucking.

Litchfield County Connecticut. We also threw a ton of stuff at each other but I think that’s more common.

cleonjonesvan

46. All Sorts of Trouble

Where do I start…I would cut up the window blinds for no reason. One day I took a lighter and decided to burn the carpet in the house. Luckily the fire didn’t spread very far. My dad smelled smoke and woke up. Sitting down hurt for a couple days after that. One random day at the park I caught a turtle that wouldn’t come out of its shell so I took a lighter and placed the flame under the shell thinking the heat would force it to come out.

I tried to smoke a Pringle. I picked up one of my uncle’s cigarettes that was still lit off the ground and took a puff. I googled 69 on my aunt’s computer and clicked “I’m feeling lucky” cause my friend told me it would lead to a game site. It went straight to an adult website and the computer was completely taken over by viruses. My uncle who was 19 years old at the time got all the blame even though he swore up and down that it wasn’t him—but of course, I never revealed the dark truth.

Darn, I hope my future kids don’t end up like me as a kid.

jackblack1356

47. Improvised Baseball

I wanted to play baseball in my backyard with my friend. I didn’t have a baseball bat or a baseball. My idea of improvising was using a pitchfork and a doll. I had no idea, but what happened next would give me nightmares for years. My friend got impaled in the knee with the pitchfork that I flung with glee after hitting the doll she threw at me. She screamed in pain (obviously), but in fear of getting in trouble, I ran to her and told her to shut up in kid language (covering her mouth like a murderous lunatic kid and saying “shh”).

My mom came out anyway to see the commotion. Somehow, I convinced her that all was fine and she went back inside. My friend stumbled home and was promptly taken to the hospital when her parents saw the injury/blood. I was seven years old.

Tri-the-gravy

48. The Special Penny

When I was about eight years old, I found a penny in my mom’s darning box—it was still a time when holey socks were darned rather than discarded. I swiped it, and used it to buy a gumball from the machine in front of the local grocery. Many years later, when I was an adult, I once groused to Mom about the trouble I was having in getting my shy and introverted girlfriend to commit to a serious relationship because she wouldn’t believe any man could be interested in her for very long. What she told me absolutely broke my heart.

Mom began to tell me about how long it had taken Dad to work through his terminal shyness enough to court her, and how his obvious internal struggle had convinced her right away that he was the one for her. She reminisced that after several months of group and double-dates, he finally worked up the courage to ask her out on their first solo date. And how that night, during a quiet moment he had offered her “a penny for your thoughts.”

She had kept that penny, she said, and had stored it in her darning box for many years…until one day it just wasn’t there.

theartfulcodger

49. The Shed

This is a story from a buddy of mine. When he was around 10 years old, he took a monster poop in the shed of a vacant house on a dare. This was in the middle of a heatwave in a New England summer, so it festered in the closed-up shed in super humid 100°F weather for a week. Turns out the house was on the market.

The realtor was taking a young couple on a tour of it. Our buddy lived across the street, so he kind of spied on them from his living room after he saw the cars there. He says that when they opened up the shed, they fell back from how horrible the stench was. The female half of the couple apparently stormed off in anger.

I’m guessing someone didn’t make the sale.

greenfox_65

50. Not Time for a Selfie

When I was about five or six I was at a friend’s house for the weekend and for some reason I got naked and jumped up and down on his parents’ bed. My friend takes this camera which he says has no film in it and takes loads of pictures with the flash pretending it’s some weird kind of photo shoot. Seriously, OHGODWHY. Anyway as it turns out the camera DID have film in it and they didn’t realize until the dad took it to get developed and got asked some very serious questions by the cops.

Yeah. Didn’t go to that friend’s house anymore after that.

Rickolas

51. Not to Dump All This on You

This was when I was around eight years old. I went to bed, and I’d always had the habit of going to the toilet in my sleep. Half sleepwalking to the toilet, taking a poop/piss, and moving back to bed with the very vaguest knowledge of what happened the next morning. One night, I did so as usual. I got up, went to the toilet, sat down and started my business.

For some reason, my mother came in after me, and started shaking me. I had no idea why, so I just kept going. I had to poop, ya know? She then started pushing me towards a seat and was encouraging me to dump on the seat. Confused, and half asleep, I did so. What the heck, it’s her problem getting feces off the chair.

Turns out I never originally made it to the toilet, instead, I took a dump in the middle of the carpeted hallway. She was actually trying to guide me to the toilet. Not the most dignified moment of my life.

Shadefox

52. Anatomy Academy

I was watching Police Academy when I was about eight. There is a scene at a beach party where there are a few naked breasts on show. My mum walks in to catch me licking the TV screen where the bare breasts were.

mataranka

53. Flipping The Love Birds

I was at my grandmother’s wedding when I was six years old. She was getting married for the second time and the church we were in was completely packed. Keep in mind this is a church in rural Alabama, which makes this that much funnier. I was sitting in the front row with my parents and sister, who was 16 at the time.

My sister turns to me and tells me that it is respectful to hold up both of your middle fingers when the bride and groom kiss. So being the loving grandson I am, I find this as a perfect and simple way to show my respect for the new marriage. So I wait, and right when she leans in to kiss the groom, I thrust my arms up in the air in a packed church, flipping off my grandmother and her new husband.

I hear several gasps and old women saying, “Oh my.” I look around with this big freaking grin on my face as if I’m doing this great service to humanity. I look at my sister and she is hunched over, with a beet-red face, laughing uncontrollably. My mom finally notices what I’m doing, grabs my arms with the grip of a professional wrestler and pulls them down. She starts cursing at me and asking me what the hell I’m doing.

I tell her what my sister told me, and she gave my sister a death glare that would make most men poop their pants. After the ceremony, she pulled her aside and gave her a few choice words. She then told me what it really meant, and I felt horrible. I was so ashamed and embarrassed. I think about it now and can’t help but laugh. My sister was a master troll.

pretzeljew

54. What’s Fast Isn’t Always Right

It had recently snowed and my car was covered with ice. In the age of instant gratification that we live in, scraping with a cheap plastic scraper was taking WAY to long. My bright idea? Use a snow shovel for a wider area of attack. I broke my back glass and passenger side window. My stepdad laughed for ages.

CrazyEyezKillah

55. Parting Gifts

When I was about 7-8 I was extremely afraid of public restrooms and really had to poop at the grocery store. I decided to sit down to relax my stomach until we got home but in doing so, I accidentally pooped. My sister walked into the aisle and asked what I was doing and I said “looking at stuff.” On the ride home, my Dad asked if I farted so I said “Uhhh, yep” and everyone thought it was gross.

By the time we got home everyone had figured it out and I was really embarrassed.

YourBestFriendStu

56. Anything for the Money

When I was around six or seven I thought any type of money was a lot. Of course, when you’re a kid you think even one dollar is like you’ve won the lottery. Well, one day I was at the mall with my mom and aunt, and my aunt thought it might be funny to test this money theory she had. I went off with her to go shopping while my mom did her own shopping.

My evil aunt offered me a crisp one-dollar bill to take off my shirt and pants and run around the mall with a pair of underpants she had bought me on my head screaming “Don’t judge me” as I ran. About ten minutes into this, I was captured by the mall cops and they called in my mom to their office. Somehow, she hadn’t seen me running around but when she stepped through that door to find her 6/7-year-old son in his underpants with another pair on his head she was completely shocked.

SkeithXEpitaph

57. Monkey See, Monkey Poo

When I was about four or five a few of my cousins were over visiting and we were swimming in the pool. I always really looked up to them because they’re 8-12 years older than me and of course I wanted to emulate them. So, we’re swimming in the pool when my cousin Jonathan decides to rip a massive fart underwater.

Obviously, being the kids we are, this is hilarious and Nathaniel (other cousin) and I try to out-fart Jonathan. Nathaniel farts a few times and we busted a gut laughing and now it’s my turn to save face and become “one of the guys.” I strain and strain and a few little toots blossom forth but nothing great. The guys are really egging me on now and I start to push harder than ever in an attempt to be cool.

“At last!” I thought, as my sphincter stretches apart for what I’m sure is about to be the most epic fart ever seen by my cousins. It was poop. In the pool. I just remember laughing so hard even though my swimming shorts were housing a log of brown polonium. My cousins were in absolute hysterics. I got out of the pool, still laughing, and proceeded to tell my mother what happened.

She grabbed the garden hose, turned it on full blast, and roared, “If you’re gonna behave like an animal then you’re gonna be cleaned like an animal!” I was then blasted with 55F water. I’m 22 now and I still haven’t lived this down and I swear that this story is told at least once at every family get-together we’ve ever had since.

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58. Fly Ball

I was a very naive kid growing up. I liked video games and computers—but my family wanted me to try out sports every once in a while, just to see if it was something that would interest me. So my Dad and I went down to the local sign-ups for T-ball when I was five. Practices went okay…I wasn’t good at it, but I tried. Of course, being the overweight gullible nerd on the team I was subject to a lot of ridicule.

It was our first game and all the parents were there, including my Dad. It was the fourth inning and I was playing center field. I had to piss REALLY bad, so I asked the guy playing right field where the bathroom was. Without skipping a beat, he said “Don’t you know how they pee in the major leagues??? They drop their pants and spin around in a circle while they pee. “It helps the lawn grow out here!”

Naturally, I went along with this and promptly pulled dropped my pants and let ‘er rip. EVERYBODY is laughing…everybody except for my Dad, who promptly got out of the bleachers and left the game. He came back 45 minutes after the game was over to pick me up. I’m reminded about this at least two to three times a year.

OpenThirdEye

59. Way to Dampen my Creativity

I was a pretty horny kid. And since I’m pretty old, there were no internets, so I used to write my own erotica in my pink and purple side lock diary. You know one of those that had the same key as every other one and hence every sixth-grade girl had the same tin key around her neck…Anyway, I would write my own dirty stories (gleaned from terms I heard on soap operas, episodes of Thirtysomething, and Harlequin books I peeked into in the bookstore) and pleasure myself on the regular. Sometimes I erased the stories afterward, in case Jesus saw, but not always.

One of the times I didn’t, my older sister came across my diary and of course read it because she’s a jerk. She then proceeded to take it (because she was “worried about my soul” I kid you not) to my very Hank Hill-esque father who, due to lack of easy-fast options, told me I wasn’t allowed to write in my diary anymore.

He later told my mother, who devised a punishment curriculum involving bible verses and yard work, which stretched my humiliation out over a week or so. My sister still owes me.

Therealemylibefs

60. Light It Up

Getting caught by my dad with a cigarette the same year he lost his mother to lung cancer. Think I was 18. We were camping, and he was coming to the island’s big fire where all the people out in the dock have beers for the night. He was bringing me one. He didn’t say a word about it. I felt so horrible—still do.

stevedusome

61. Background Noise

When I was 16-17 my first serious girlfriend and I used to bang like rabbits, like for hours, in my bedroom across from my mom and sister. It was only like four feet from our door to theirs. Later they told me “Yeah duh, of course, we knew… we heard you banging X like every night for a year.” I have no idea why they put up with it the whole time.

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62. How About a Whole PACK of Condoms!

I brought a girl home when I was 16. She spent the night and the next day my dad walked in as we were sleeping, introduced himself, took me to the kitchen and handed me a box of Trojans. The economy family value-sized box. In front of my entire family. Upside down. open. And he had separated each of the 150 condoms from the roll.

Cue me scooping armloads of condoms into this freaking box while everyone is watching. Why, dad, why…

rosesareredviolets

63. What a Sight

My Grandmother caught me standing on the sink bent over in front of the mirror looking over my shoulder all because I wanted to see what a fart looked like.

HAHno

64. Ta Ta for Now

When I was about seven, I was in love with Tigger. Obviously, the best character in Winnie the Pooh, I felt compelled to be like him on every level. I would jump around the room yelling about all the wonderful things about Tigger. One day, my mother had some ladies over for some Bible study or something. She told me to stay in the room while they would chat, and that I shouldn’t run around and be too distracting. Screw that noise, I was Tigger.

To up the ante, I went to the bathroom and wanted to find something to give me some stripes. I found a box of neon band-aids and got butt naked and put that stuff all over my body. I ran out of the bathroom and decided to show off my stripes, so I jumped into the living room with 15 middle-aged women staring at me and my neon green, purple, and yellow stripes.

To this day, they never let me live this down and have a photo of it that they show to all the dates I bring back to the house.

groteklotzaak

65. Open Door Policy

When I was about five or six, my mom used to make wedding/prom dresses for girls/women in our church, and one day one of these fine ladies was over trying on the finished product. It was bath time for my brother and I (shared bath to conserve water for six siblings). Our house back then had the stairs directly in front of the front door/foyer. The upstairs was open, so you could see our bedroom door, and the bathroom door at the top of the stairs.

So, not wanting the parents of this girl to notice me in my oversized t-shirt that I wore as PJs, I decided to run to the bathroom. I make my quick 15′ dash to the bathroom, swing open the door, and there is this girl in her undies (early 90’s era panties/bra). She screams, then I scream, then the parents burst into laughter. I slam the door closed and run back to my room and slam that door. The laughter continued for a while, and I stayed in the room until the girl and her parents left…

hereticnasom

66. The Party Don’t Start ‘Til I Walk In

Alright. Me being ten years old at my neighbors birthday party. Were all stupid little kids jacked up on Mountain Dew. 3 o’clock in the morning and were playing truth or dare. My friend dares me to take off all my clothes and run down the hall screaming “I’M A PARTY BOY.” My neighbor has a huge hall. So I take off my clothes and run down the hall with underwear on my head screaming “I’M A PARTY BOY.”

As I’m turning around my neighbor’s mom opens the door, looks at me from head to toe, and whispers “Good night,” turns and closes the door, and runs upstairs. I pissed myself.

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67. What Are You Looking At?

I thought my family was out of the house during middle/high school. While I was taking a hot tub I decided to do some buck naked headstands under the water, at the same time my mom and sister looked out in the yard…

SerKnight

68. A Bird’s Eye View of the Action

When I was 41, I went to visit my parents and had to take a dump. For some reason, when I sat on the familiar, family throne, I had the urge to jack it like a teenager. I heard a sound above and just briefly caught a glimpse of my 70+ dad’s face disappearing from the skylight he was re-sealing.

quiettime

69. Work What Your Dad’s Girlfriend Has Got

Oh boy. I was watching the Victoria Secret Fashion show. I was around eight so I was not interested in girls. But they were wearing underwear that looked comfortable. I knew I could find a pair in my dad’s drawer. Now I didn’t have a mom, so this was from his girlfriend we didn’t know about. So me and my brother put a pair on, took everything else off, and started doing flips off the bunk bed.

My grandma hears all the commotion and walks into my dad’s room only to see me and my brother flipping off a bunk bed wearing nothing but girls’ underwear.

Maybenotnow

70. Man’s Worst Role Model

When I was like seven years old my entire family was having a barbecue at my house. There were probably like 15 people in total at my house. While enjoying weenies and burgers I noticed my dog dropping a dook in the backyard. For some odd reason, this sparked some kind of mindless epiphany in my head, and I found it would be an excellent idea to follow in his footsteps.

So while everyone was sitting at the table eating, I walked up to the nearest patch of grass and blooped a fat duke in front of everyone right on the grass. EVERYBODY laughed right in my face. It was easily the most embarrassing thing to happen to me. On the bright side though, it was hilarious watching my mom pick up my poop, since she was on the verge of vomiting everywhere.

Maximillianz

71. A Blessing from Above

When I was probably seven years old me and my brother would be hanging out upstairs in our room. But there was only one bathroom in the house and it was downstairs and allll the way on the other side of the house. Our solution: pee in bottles and throw them out the window. Little did we know we threw them out the window to the backyard where my entire extended family was…

surgency23

72. Don’t Sweat the Small Stuff

I broke up with a woman I was head over heels in love with over something that, on reflection, was fairly minor. Spent half a year progressively dropping into a deeper and deeper funk. Wouldn’t admit it to myself, but I had clearly made the wrong choice. I was hanging out with a friend when she pointed out to me that she had never seen me as happy as I’d been when I was with my SO.

Another friend pointed out that same week that the music I’d been DJing had become much more depressing over the past few months and asked me if something was wrong. That woke me up and made me realize how special she had been. It took another year for me to realize she was the first woman I’d really loved in the way you come to love somebody for who they are, rather than what you imagine them to be.

I never saw her again. I wish I’d never left her. We only would have had six years together, as she came down with cancer that eventually killed her. It didn’t change how I felt; I’d take those six years with her in exchange for all the years I have left if I could.

helldeskmonkey

73. Cheesy Tunes

About a year ago, my parents caught me singing to my microwave while I was waiting for it to warm up a piece of pizza. This all happened at 4 in the morning, when I thought my parents were staying at a friend’s. Oh, I almost forgot that I was naked.

About23Koalas

74. There’s No Place Like Home

I bought the house we had been renting for a few years without getting a proper inspection first. We were trying to do it for super-cheap, and I told my wife, “Look, we already know everything that’s wrong with this house. Why bother getting an inspection?” Follow up: We did not know everything that was wrong with this house–nor did we realize how expensive it would be to fix those things.

edgarpickle

75. Horsing Around

I’m five years old and my next door neighbors take me to meet their horses. The mom gives very clear and explicit instructions on how to handle the horses properly, and proceeds to start brushing one of them. In my infinite wisdom, I defy all of the instructions I just received and walk directly behind the horse to very timidly graze its beautiful tail with my small hand.

With lightning speed, I’m hit with a degree of force that I wouldn’t again feel until I was in a huge car accident many years later as an adult. I’m launched out of the stall and fly halfway across the common area until I thump down on the floor. As I lay there, stunned and gasping, for breath, I know that I definitely should not have done that.

skinnydippindiarrhea

76. You’re Toast!

I touched the coil in a toaster with a knife while it was switched on. When the power in the house cut out, I realized I probably should not have done that. When I told my father what I’d done, I knew for sure that I should not have done that.

saint_david

77. Blinded by Beauty

I was a stupid kid. A really hot girl decided she wanted to date me, so I broke up with the other girl to date the hot one. Hot girl turned out to be shallow as heck and we broke up not long after starting. Other girl ended up being basically my dream girl. Absolutely beautiful, smart, funny, great personality, down to earth, etc.

She and I remained friends for a long time, but even though she still had feelings for me, she wouldn’t actually get back with me because she never trusted me again.

monarch_j

78. Jumping For Joy

During fourth grade, my parents remodeled our kitchen. This involved digging up part of the foundation to rebuild the deck. As such, we had a giant pile of dirt in the backyard. When I went to play on it (who can resist a pile of dirt, am I right?), I jumped off, tripped, and fell face-first not into the dirt but onto the concrete beside it. Immediately, I knew that something was wrong.

I ran inside, opened my mouth, and looked in the bathroom mirror to find that I’m missing about a third of my top right front tooth. I distinctly recall saying out loud, “Yup, it’s gone” and regretting having attempted the jump.

jmorlin

79. Wok and Roll

I got distracted while my wok was heating up with some oil in it. When I snapped back to reality, my hand just automatically threw in the dried chili flakes. It was like an out of body experience. My brain couldn’t stop my hand in time. And that’s how I maced myself…and my dog.

Aggressivecleaning

80. A Royal Flush

When I was a kid, I was horsing around and ended up totally destroying one of the house plants by accident. No kid wants to get in trouble so I decide to get rid of the evidence. How? Flush it down the toilet, of course!. So I walk into the bathroom feeling like I got this, but none of the dirt goes down at all, obviously. I’m panicking, just flushing and flushing for 20 minutes straight.

It all goes down eventually but I probably destroyed our plumbing system. Whoops…

Ackebo1

81. Major Return on Investment

When I was 16 I briefly dated a girl who was 17. She wasn’t in my peer group; she was an “outsider.” But she was nice, had curly blond hair. I liked her. She had an old 1970 Cadillac and she let me drive it. I had never driven before, so maneuvering that giant boat on the narrow streets of town was… fun. After a few months, my friends were bugging me about why I was wasting my time with this girl. She didn’t smoke or drink or listen to hard rock. So I let us drift apart. It was the biggest mistake I’ve ever made.

She turned 18, graduated high school and then won the New Jersey state lottery for $6M. I should have stayed with her. My friends were all bums.

CitizenTed

82. Won’t Be Needing This…

When I was six years old, I hung out with a few neighbors around the same age in the back area of a local park, where we found this weird shoebox, half-buried near the edge of a creek. We were apprehensive at first, but in the end, we dug it up and opened it—I couldn’t believe what we found. Inside were a few ziplock bags of white powder. We ended up just tossing the bag into the water and leaving it there.

In hindsight, throwing away what might have been a criminal’s expensive drugs was probably not smart. You generally don’t want to get on those people’s bad side…

some-dork

83. Hello, Dolly

I once lost control of a dolly and the refrigerator that was strapped onto it. When it started bouncing down the stairway like a rocket, I had the thought that I probably shouldn’t have been so careless with how I handled it. My suspicions were confirmed a mere second later when it slammed full speed into the concrete wall at the bottom of the stairs and came to a dead stop.

Not surprisingly, the refrigerator never worked properly after that, so I immediately had to lug it back out of the basement and best of all, pay for the damages. 0/10. Would not recommend.

KingOfAllWomen

84. Home Alone

I decided to go to my insane ex’s house alone to pick up my stuff that I didn’t actually care about. I don’t know what I was thinking. We had broken up recently because she tried to stab me when I got home from drinking at the bar with a few friends. Thankfully, I lived to tell the tale. But I still probably shouldn’t have done it.

Frekkes

85. You Probably Should Have Kept That Private…

When I was around 12 years old, I noticed that nail polish remover felt cold and kind of nice as it evaporated from my fingers. So I decided to put some of it on my private parts…

littlest_ginger

86. Chances Are

After many years of refusing to see him, I finally gave my abusive dad a second chance to be in my life. He hadn’t changed at all.

Jazzmim_999

87. Unholy Matrimony

I got intimate with a married coworker. It happened a long time ago and I was in a really bad place at the time. I realized right away that I shouldn’t have done it, and I still feel horrible about it.

BlondeSummers

88. Instant Karma

I once pushed a pot of hot oil off of my friend’s stovetop as a joke. The funny thing about physics, though, is that the oil splashed right back at me and landed all over my hand.

Rednaxxela

89. Dishing It Out

I had some dirty dishes from spaghetti and I was out of the detergent that’s made specifically for the washer. Obviously, I don’t want to wash them by hand so I just pour regular dish soap into the machine, feeling like MacGyver. I didn’t realize how wrong I was until my entire kitchen looked like a foam party. Definitely should not have done that.

Rzr117

90. Food For Thought

I have the “I shouldn’t have done that” feeling each and every time that I buy drugs for myself instead of food—which happens more often than I’d like to admit…

bout2getweird

91. The Glass Is Always Half Full

I broiled burger patties on a shallow cookie sheet, causing the small lake of grease that accumulated to catch fire and nearly burn down the house. On the bright side, the burgers were great!

Happyhandse

92. What Really Matters, Buddy

Someone I know left his wife because he felt the intimacy was awful and he wanted someone with whom he felt he could have great relations. Wife pleaded with him to stay (no kids) but he refused and filed for divorce. Divorce is finalized about a year later. This guy dates lots of women, but still finds the the intimacy unsatisfactory.

Meanwhile, ex-wife meets this other guy about a year after the divorce and they have that type of whirlwind romance that truly is like something straight out of a rom com. She marries this new guy, they have kids and the perfect marriage. She tells everyone that the divorce was the best thing that ever happened to her and can’t believe how happy she is and could never have previously imagined that a marriage could be so wonderful.

The guy, who is my friend, is more miserable now than ever. Constantly says what a mistake he made leaving his wife. Doesn’t even go on dates anymore and has not had intimate relations in years.

Analytica0

93. Mom’s Little Cross to Bear

When I was around 10-11 I went through a really rough patch emotionally. The drugs I was getting for my ADHD started messing with me really bad, and that combined with regular pre-pubescent angst turned me into quite the little monster. I started getting into a lot of fights in school and was generally an emotional wreck. I’d get so mad I couldn’t express it and would instead just be a jerk to everyone around me.

One night, I was on the couch with my eyes closed, basically being quiet for the first time in months, and I heard my mom say to my brother that raising me was really hard and that sometimes she wished I was just someone else’s problem. I know she was just tired and frustrated, but I’ve never forgotten that, and I’ve also never confronted her about it.

adamanything

94. Martha Stewart Wouldn’t Approve

When I was about eight or nine I was going to the bathroom and noticed an open box of nice cotton things on a string wrapped in plastic. “Amazing!” I thought and continued to unwrap every single one of them. I then hung them up around the bathroom in various places (door handle, taps, anywhere they would hang) I even hung them over my ears, tucking the string behind my ear so the nice cotton things sat in front of my ears, like fluffy sideburns.

Anywhoo, so I had been having an excellent time for about half an hour at a guess, and my mum knocked on the door to see why I had been in there so long. I happily opened the door, ready to show my mum my beautiful creation of hanging nice cotton-things. She found it funny, although wasn’t as appreciative as I had hoped she would be.

StarSelect

95. An Important Lesson to Learn

(Then age 22, now 29) Loaning an ex $10,000. He cheated and never paid me back. I learned the valuable lesson to never loan money you can’t afford to lose.

ClaimedBeauty

96. Cherish Those Around You

An ex of mine. It’s a long story, but she still haunts my dreams. While we don’t talk anymore, we did clear the water a couple of years ago and I got closure, mostly. So I’m not going crazy over her, but a part of me will always miss her. She’s a hole in my heart that I carry proudly, as weird as that sounds.

I’d like to add, as I totally missed the point of the question, was that I regret the way the relationship went, and not her. She’s the best thing that ever happened to me, and I’ll never forget her.

GiantEnemyMatt

97. Always Be Safe

Not wearing a condom—even though I knew the girl got around a little bit—and contracting genital herpes. Now I have to share my herpes with my wife and she lived a perfectly safe past. I wish she didn’t have to deal with it, it’s my cross to bear.

EanmundsAvenger

98. The Things We Wish We Could Change

I’m 28 and what I regret most is not killing the guy who assaulted my girlfriend. He was my best friend in high school, but he had messed up views about women. If they dress a certain way they deserve it. If they flirt with you they owe you. That kinda thing. She told me months after the fact that he attacked her while I was away for a few days.

It took every bit of control to not track him down and kill him then. But I knew she needed me there with her more than anything else. When I confronted him, I screamed, and I was so mad I cried the entire time. But I never hit him. I knew if I did I wouldn’t stop until the cops pulled me off of him. I took the high road and looking back, it makes me feel like a coward. I should have done something. ANYTHING. But all I did was talk.

Almost a decade later, she and I are still together, and we’ve both gotten our treatments. She’s almost all better now, back to normal. I still have major trust issues. I haven’t made a new friend since I confronted him, and I’ve cut almost all ties with the few I had at the time. I just can’t bring myself to do it.

6speedhemi

99. You Can’t Go Back

I should never have kissed my ex-wife on Labor Day 1997. It was the worst decision of my life. I wish I would have just told her to screw off and said I had no interest in talking to her at all. She was a virus that destroyed me and consumed my will to live. Then she moved on. That is the only thing I wish I could make not happen in my life.

Not failing to save my father’s life or the abuse from my childhood, just her. I regret everything about her.

Dummystupid

100. The Assassin

I tried to poison my mom’s boyfriend. I was probably around 11 years old. I had one of those science kits from the Scholastic book fair. I took the citric acid and dumped the whole container into his drink. He sipped it and just said, “this tastes like trash” and dumped it out.

Zipperpants

101. The Laundry Pile

My family had a dirty clothes pile. We didn’t have a dirty clothes basket or anything like that. We’d pile it near the washer and whenever my mom had time to do it, she’d throw it in the wash. This pile was next to my bedroom door—which gave me an idea that I now realize is absolutely horrifying. Using my stupid kid logic, I decided that instead of walking down the hall to the bathroom, I’d just pee on the pile.

Made perfect sense at the time; the clothes were dirty anyway! My poor mother had to wash really foul-smelling dirty clothes as the pile usually took about three days before it was enough clothes to be washed. I still feel bad about it. Love you Mom!

Vangidion

102. Bringing Down the House

I tried to get my ex-wife served with divorce papers, only to learn she had vandalized and abandoned our former home in response to my leaving.

I went over to find almost all of my clothes had been bleached, along with our new living room set. The new dining room table and chairs had been gouged. Weeks worth of trash and raw food had been left out. The refrigerator had been turned off, leaving hundreds of dollars worth of food to rot. The whole place smelled like death.

She had also taken all of the electronics (probably to hawk), my passport with stamps in it from around the world, and the painting I had inherited from my beloved grandfather who had passed away (she knew this would hurt me the most).

All said and done, there was $7,000 in property damage and another $1,500 in stolen property. I filed a police report but sadly, not much was done about it.

IntlMysteryMan

Sources: 1, 2, 3, 4, 5, 6


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