Nobody’s perfect…but we could all do better. Reddit asked these flawed humans to share their experience of turning around to realize “Oh no…I’m the jerk". From kicked kids to revenge served too cold, there’s no limit to the how regrettably cruel we can be to each other. Does acknowledging it help? Find out with these cringey stories of people waking up to their own jerkiness.
1. No One Should Settle for Seconds
I dated my best friend's ex-girlfriend. The actual worst year of my life.
2. Is There Anybody Upstairs?
In the past, I'd subconsciously tune people out in the middle of conversations, and then give a rehearsed response when I could tell that it was time for me to respond. I didn't even realize I was doing it so much, but then I noticed I kept asking my friends about all these things that they claimed to have already told me.
When I realized it was a problem to be such a bad listener, I made a conscious effort to fix it and I'm much better about it now.
3. Don’t Shoot the Messenger
I moved to live closer to my best friend and work with her. Ended up hating the town, taking it out on her, spending all my energy complaining about how I’d ruined my life and not gave any thought to her feelings. I moved away and we’ve kinda repaired things, but it definitely left an impact and I was 100% in the wrong.
4. When the Sun Sets, so do the Yeehahs
A friend brought my group of friends to a bar on Halloween weekend. I was dressed up as a cowboy. I noticed that pretty much everyone else at that bar was dressed as a vampire. I went around and complimented a lot of them on their awesome vampire costumes. We eventually left and hopped over to another bar. I'm telling my friend I thought it was weird that everyone there had chosen to dress as a vampire.
He tells me that we were actually at a goth bar, and none of them were wearing costumes.
5. Just a Bit Off the Top (Of Your Self-Esteem)
When I was a kid, my dad gave me a dollar to tip the lady who had just cut my hair. I went up to her and said, "I'm gonna regret this," and gave her the dollar. I was trying to make a joke about how I'd have less money, but I didn't realize how it could have come off as a criticism of the job she did until my dad explained that to me.
6. Not the Manners of a Master
Taekwondo instructor here. "Lightly" kicked a student in the leg because he was being annoying. He gave me a sad look. I felt bad and had been trying to be nice to him ever since.
7. High Volume Pettiness
Back in my rage-all-day-everyday college days, we'd routinely party until the sun came up. One time, a roommate came downstairs and turned down our music. As he was walking back upstairs, I cranked it back up. He came back and started jawing at me about respect and I wasn't having any of that. Huge jerk energy on my part.
8. Keep the Change. Seriously.
When I was a teen, I went to a restaurant with several of my friends. We had been at an arcade earlier, so I had a pocket full of quarters. My tip that night was quarters sprinkled in glasses, in food, and on plates. Thought it would be funny, but I look back on it now and it wasn't. It's something for which I'm deeply ashamed and it fills me with regret every time I think of it.
Now I am extremely nice to the wait staff.
9. Alone With the Herd
We were on a family holiday in a caravan park by the sea. I was probably 10 years old, maybe eleven. There was a large number of kids the same age as me who would hang around together. One of the kids was from the country and awkward. The crowd as a whole decided to exclude him from the activities by basically ignoring him.
Being young and easily led, I decided to follow the crowd. He came over to play football and everyone walked away from leaving him by himself and crying. He shouted out, “I thought you were my friend!" whilst bawling his eyes out. To this day, thirty-five years later, I can still hear him. Wish I had more backbone as a kid.
10. Ladies Love to Walk
When I was a little kid, I mixed up the words "lesbian" and "pedestrian". Long story short, there was a circular park near my house that my mom would walk around for exercise. I would ride my bike next to her. As she was walking, I was riding ahead of her trying to clear a path by saying, "Excuse me lesbians" instead of "Excuse me, pedestrians".
11. The Heart Should Be Handled with Care
Back in seventh grade, this really shy girl used to have a HUGE crush on me. Her friends told me she would leave PE early to go to the changing room in order to look pretty for the next class that we were both in. Then, her friends kept asking for me to talk to her and ask her out, but I refused because to me, "She looked like an alien".
Unfortunately, her friends told her, and she was devastated. I was honestly just stating why I didn’t want to "date" her, but I realized how freaking mean and terrible my comments were. I apologized to her for being an insensitive jerk and she forgave me. We managed to become friends in eighth grade and all throughout high school.
I still feel bad about whenever I think of her.
12. The Fine Line Between Rude and Desperate
I went to a concert. Did some drinking in the parking lot. Start walking towards the venue and really have to pee. Getting to an area with lots of people around and no discreet location. Think I'm gonna wet myself. Get close enough where I can see the row of about 20 porta-potties. Get tunnel vision towards my target and B line it to the closest one.
Just as I reach for the handle it opens up. Perfect timing. I go in and relieve myself. Come out and realize each porta-potty had a line about 30 people deep. I just cut about 600 people. I felt bad, but worth it to not wet myself.
13. Never Judge an Artist by Their Wares
Setting up for a huge artisan trade show that involved a massive vetting process (it was very difficult to be selected). We had a day to set up, and as we’re all working our butts off trying to make the BEST display of our goods, one booth across from us remained a total ghost town, to the horror and shock of the rest of us "hard-working" artisans.
Fast forward to the opening day of 10 days of this massive Xmas artisan show (as in HUGE!!) and the empty booth owners show up, set up a basic Costco table and dump cardboard boxes around. We’re all rolling our eyes and snickering at this point, I mean...come on??? What LOSERS!!! Yeah...those "losers" were selling authentic Peruvian sweaters and hats.
Sold out in three days, packed up their Costco table, humbly leaving with WAY more than we could ever hope to make. Meanwhile, the rest of us shmucks had to kiss butt and keep our pathetic grins on for another seven days. I will forever look back on that experience as a lesson of making assumptions and being a total jerk. Which I was.
14. The Bloody Truth is Not a Meme
My best friend and I have this gif that we send to each other on the first day of our periods, the one from The Shining with the elevator doors opening and the blood everywhere. After her first miscarriage, I spaced and sent that to her and have hated myself ever since. Pretty sure she doesn’t remember, but I’ll never forget.
15. I Wouldn’t Book That One-Way Ticket
I broke up with my girlfriend of three years from a subway station pay phone in Germany. I was getting ready to live there for the year, and she was planning on moving there with me in a few months (she was living in the states at the time). She was supposed to come out to visit me and check things out that following week.
I felt terrible, but it was clear to me we had no future, and I hadn't really been able to admit it to myself until then. I was totally the jerk. She blocked my email not long after that.
16. All That Glitters Isn’t Gold...It’s Silver.
I still feel bad about this even though it isn't a huge thing. I went to a restaurant I am at all the time. I know the staff, they know me. I sat at the bar like I usually do and ordered a steak. The waitress isn't paying much attention even though it isn't busy. A runner brings out my steak and sets it down in front of me before disappearing back into the kitchen.
But, the problem is, I have no silverware. For some reason, this annoys me. There is no silverware set out on the tables I can grab, the waitress (who is also working the bar) isn't paying much attention. So, I wait for her to come over. I could have yelled for her, I could have gone over and tapped her on the shoulder, but I wait.
30 minutes later she comes over with my bill. Looking down she sees that nothing has been touched. Surprised she asks, "Was something wrong with the steak?" I say, "I don't know, I didn't have any silverware to eat it with..". in exactly the cheesed-off tone you would imagine. She apologizes and offers to go get silverware, but I tell her its cold now and I have to get back to work. I pay my bill, leave no tip and walk out.
There was no reason for me to be a jerk. I apologized to her over and over again afterward. It had been a frustrating day and I took it out on her. It was well within my power to get some silverware; I was just being a jerk.
17. All Signs Point to a Set-Up
I had a terrible job in a warehouse and was getting bloody noses every single night because there was so much dust everywhere. One night, I put up a sign that said, “This Job Sucks” on one of the pillars in the back. The next night, the line manager bought us all ice cream and as he was walking through the warehouse, he saw it.
Everybody knew that I had done it, but no one was going to snitch. Meanwhile, there was this annoying kid named Brandon who was cheesing me off and for some reason they suspected him. The next night, I almost got into a fight with him over some stupid stuff and at the end of the shift, they fired him, thinking he had put the sign up.
I totally got away with it.
18. You Can’t Scream a Seed into Becoming a Tree
Many years ago, I was just starting out on a new position as a project manager. Things weren't going smoothly on this project, not really in anyone's control, but it added stress to myself and my team. One day, one of my teammates made a minor and fixable error, but I still screamed at them in front of about 10 people (all employees).
Like a good two-minute rant about what an idiot they were. They were a summer student, making minimum wage, and I just laid into them. The worst part is that they made the mistake because I mislabelled something. Some 10 years later, I still manage small to medium teams and I think about that moment a lot. It reminds me to keep my cool in stressful situations, and you can provide discipline without being a jerk.
Also, now I feel like owning up to your own mistakes as a leader actually helps the team grow long term and establishes trust with your employees.
19. Worn-Out Welcome
After getting kicked out of school, I overstayed my welcome at a close friend’s house. I lived there for like three months. I never really asked to move in. I was living on the couch. They just kind of said that I was moving in one day. I explained I didn’t have any money but still moved into the room when the roommate left.
Eventually, they kicked me out for not paying. I should have just left. I had parents I could return to. I was homeless by choice.
20. World’s Worst Telephone Game
I was bullied in elementary school, the worst of which happened around the fifth and sixth grades. In seventh grade, things began to improve a bit, and by grade eight they were pretty much okay, but I still carried a lot of that trauma. In eighth grade, a girl in my class, who was not part of, but who was friends with the people who had bullied me, asked for my number so we could text each other over the march break.
I gave it to her, reluctantly, and said, "Fine, but you know I'd never actually text you right?" I still remember the freaking crestfallen look on her face. I still feel awful about that to this day. I let what those kids did to me embitter me to the point that I didn't believe that someone who was friends with the "popular" crowd would interact with me without it being some sort of cruel joke.
I apologized to her a couple years later in high school, when I got over a lot of my misgivings about people, and she explained that she had felt so bad about what had gone on with her friend group and I, because she had realized that year that everything they'd said about me was false. She was being genuine when she asked for my number, and she wanted to try and make up for all the horrible things they'd done.
Despite the fact that she was upset and initially didn't understand my reaction, she stated that she understood at that point what it had probably looked like in my mind, and that she didn't blame me at all for reacting snottily. We're all good now, but I'll still always remember that moment as an important reminder for myself.
Sometimes people are genuine, and sometimes they're kind, and that when you assume that everyone is bad all the time you miss out on some really great people.
21. It’s All Fun and Games Until It’s on Your Dime
When I was in high school, my friends and I used to put together these scavenger hunts where instead of finding things people had to do things. It was mostly pretty innocent dumb stuff like eat six raw eggs or argue with a street sign for five minutes. Anyway, one day we had a hunt planned, but it started raining so we went into the Water Tower Place in downtown Chicago to wait it out.
While there we got the idea to play a giant game of tag since we couldn't do the scavenger hunt. There were about 10 of us total just chasing each other around throughout all the stores and floors, and we were having a blast. About 15-20 minutes into the game, me and a couple of other people that were around me got stopped by a security guard.
They were kicking us out for what we were doing. One rule of the hunt was everything you did needed to be documented in some way, so I had a digital camera on me. This was back before everyone had the means to record on them, so the security guard had no idea I was videotaping him as he escorted us out. We all, of course, thought it was hilarious, us being kicked out for having a little fun.
Fast forward to several years later and I'm working as a cashier at Borders. A couple of little kids start chasing each other in the store and end up knocking over a display. I had to go and clean it while these kids ran away laughing, which annoyed me. It was then that it hit me: "Holy moly, we were being such jerks".
We had definitely knocked over quite a few displays that day, which was part of the reason they had security guards walk us out. We were probably such a huge pain in the butt to a lot of people that day, but we just didn't see it that way because we were dumb teenagers.
22. The Wrong Foot Forward was Mine
I'm darn lucky this person didn't hear what I said but I was a jerk, nonetheless. My ex and I were driving home from dinner one night. I notice a guy running oddly down the street a block or two ahead. I pointed him out to my ex and joked the runner must be inebriated or something. We catch up to the guy and that's when I notice he was wearing an Army hoodie and had prosthetics on both legs.
I have never felt more ashamed of myself than I did in that moment.
23. His Loss is No One’s Gain
When I was in elementary school, there was this kid who lost his father to cancer during the school year. One day after he came back to school (can't remember how long after), we got into some sort of dispute on the playground. I don't remember exactly how it came to me saying, “At least my dad isn't dead," but that's exactly what came out of my mouth.
I spent the day in the principal’s office. To this day, this is one of the biggest regrets of my life and I'm 23. I still feel terrible about it because I never got to apologize to the kid because we moved away shortly after. I don't even remember his name, but I'll never forget saying that.
24. The Worst of the Verse
OK, in my very slight defense, my boyfriend at the time in high school cheated on me with a very, very innocent exchange student who was only 14 (even though she looked 11). He was 17 or 18 and I was furious, not so much because he cheated but because I loved that little kid and after he used and dumped her, I found her sobbing so hard in the bathroom that nobody could even understand what she was saying at first. OK, so he was a jerk too...but then there was me.
My dude was stupid, like genuinely very dumb. Typical football jock who'd been socially promoted probably since kindergarten and could literally barely read. I was an honor student. We were a bit mismatched. He knew I wrote and read poetry, so he took it upon himself to write me a poem every day. Needless to say, they were littered with spelling and grammatical errors, but also, they just sucked.
He would often say, "I'm terrible at this, I'm so stupid," but I would say, "Noooo, I love them, they're great!" I had been encouraging him to learn to read better and had even convinced him to go to after-school tutoring sessions with my English teacher, who was nationally known for her work helping illiterate or semi-literate people.
So, he had been making some progress and I didn't want to discourage him by saying, "Uh yep, these are real trash". Well, after he screwed and dumped my little French friend, I SHOULD have dumped him with a big lecture. But instead, I took all the poems he had written me, corrected them in red ink, tied them in a bundle with a red silk ribbon, and left them in his locker with a note that said: "You're right, you really are an idiot".
For some reason, High School Me figured he would know that news of his cheating had reached me and understand that my note meant, "You're stupid to treat me this way" and that the corrected poems were my way of being a jerk to him. In other words, I was even dumber than he was. I lurked between classes until he opened his locker, stared in shock at the pile of blood-red poems, read the note—and let out a wail like a sad dog.
He burst into heaving sobs and as his football buddies gathered around him, he cried "I knew it!! She's so smart and I'm so stupid! I don't even know why I tried!" I tried everything I could after that to explain that I didn't mean it, but of course, I had no ground to stand on after having corrected his poems like that.
He dropped out of tutoring and, as far as I know, never really learned to read. I still worry that his life sucks and I'm part of the reason why. And not only that, but he never even had a clue that I knew about the other girl, nobody ever called him out on that, and he probably kept right on seducing the most gullible girls he could since he had a total inferiority complex.
That's the only time I ever really fought dirty in a break-up, at least I learned my lesson, but I still feel awful.
25. Don’t Expect a Postcard
When I broke up with my high school girlfriend of three years, I was the jerk, hands down. Nicest girl ever, I feel like a piece of trash to this day. I thought it was understood I was going across the country for school, this had just been a good high school run but we weren't gonna do this extremely long-distance deal in college.
Apparently, she didn't know that...at all. I don't know how she kept it together when I, looking back, was very callously telling her, “Yeah no, we're not gonna be dating in the fall, thought you knew that". I don't know why our families are still friends. She met a missionary after that and is now happily married and I think expecting their second, so maybe it was all meant to be for me to be a total jerk and scare her in the right direction.
That still keeps me up at night at times though thinking about it.
26. The Rule(r) of Law Means Nothing Down There
Back in the fifth grade, there was this kid with a really cool ruler (one of those blue and green ones that's rubber and you can bend it and whatnot). One day, I decided I was going to take it. It was during recess, and no one noticed me, and my plan was dutifully completed. I tried being smart about it and didn't start using it until a few days later, but the kid found out and told the teacher, so I lost the ruler.
10-year-old me thought, “That’s not fair! I stole it fair and square!” I eventually came up with the thought that if I couldn't have it, neither could he. So again, I took the ruler during another recess, but this time, I decided to drop it into a drain, never to be seen again.
27. A Soft Touch to Hard Labor
I was an hourly manager at a local restaurant, where only four or five of us worked on a shift. We had a teenage girl working, and I didn’t really think about it, but I was entirely too hard on her because she had been a bit lazy in the past when she worked on my shifts. One night we were closing, and apparently the entire night I had just been mean as heck.
Come to find out I made her cry and she told her mom. Mom shows up the next day and asks for me. Didn’t even know I made her cry, but I felt like a gigantic jerk. Apologized and we were good from then on.
28. Not All Paths Should Be Followed
I remember when I was around 12 years old and I was in a pool at a hotel with my cousin and sister. I really needed to poop, but my little kid mind thought I had time. Eventually, I finally got out and wobbled to the bathroom. Unfortunately, I was too late and as soon as I got in, I started pooping. After washing my swimsuit in the toilet, I got out and left with a huge trail of poop on the floor leading to a stall.
A couple hours later, I saw the janitor wiping the floor and mumbling to himself angrily.
29. Throw Me Into the Doghouse
Friends of mine had run over their dog a few months ago and had recently gotten a new puppy. I jokingly said, "Try not to run over this one!" The second it left my mouth I realized what a jerky thing that was to say. The punch that I received was well deserved...
30. He Who Smelled It Can’t Have Dealt It
I was at the McDonald's Play Place with some of my kids a few years back. Two boys who I assumed were brothers came down the slide. The bigger one said, "It stinks in there! I think somebody tooted". Completely forgetting that I'm not among my friends, I point to the other kid and raise my eyebrows like, "I think he did it".
The other kid gets all sad looking and backs away from me. I said I was sorry and just kidding, but it turns out they weren't brothers or even friends and the damage was done. The kid gave me the stinkeye as he left with his grandpa shortly after. Basically, I was a Vince Vaughn character.
31. A Battle as Old as Time
Once I was having a smoke outside the bar in my hometown doing whatever, being young, when, on the way in, this guy makes some crack at me about how I was dressed. I got pretty mad about it and lipped off to my friends. This got back to the guy inside, who had some mutual friends or something, and he ended up asking me if I wanted to step outside.
My blood already having being fired up, I looked at him and just said, "Ya, let's do it," and another guy near my age steps out with us. In the lights of the entrance as we get outside, just as I'm going into get-ready-to-scrap mode, I get my first clear look at the guy...he had to be near 60 and was not a large man by any means.
Still, never underestimate people. It was at exactly this moment that I realized: A) I was going to fight an old man outside the pub and kick his butt, looking like a piece of snot or B) I was going to get my butt kicked by said old man and look like a complete tool. In that moment, I actually had the exact thought: "Oh, I'm the jerk here".
He said he didn't realize what he said would get me so mad and apologized, and I said I overreacted and made a fool of myself. We went off on our separate ways, but still, sometimes I look back on this whole thing and just think, Jesus what were you thinking?
32. The Mother of all Jerk Moves
I unknowingly made a “your mom” joke to a guy who had lost his mother. He said nothing in response, but I remember his sad expression to this day. This was over 10 years ago and the memory still haunts me.
33. Let Me Add to the Trash Pile
I was on holiday in an unfamiliar city and was in desperate need for a public toilet. I finally found one inside a shopping centre. The only available cubicle had an obvious blockage and a pair of men's underwear jammed in there too. I had no other option but to use that toilet. I did my business on top of the existing mess, had a failed attempt at flushing, and walked out of that room as the cleaner entered.
I felt bad.
34. Look for the Signs
In an unfamiliar area several years ago, I missed a yield sign gaining speed entering a freeway on-ramp, causing the guy with right-of-way to have to brake hard to avoid the collision. To be honest, I didn't even notice that two flows of traffic were merging on the ramp until it was too late to yield...the apparent "main" flow onto the on-ramp was a hard curve coming from my left and below the level of my straighter approach, but they definitely had right-of-way.
I'm really glad the other guy realized I didn't see him and slowed and laid on the horn. Scared the snot out of me and probably did the same to him. I tried my best "I'm sorry" gesturing, but he remained understandably unimpressed. No damage, just cringe whenever I look back at it.
35. Understand the Weight of Your Own Words
I was at a friend's house, and his mother ran an after-school babysitting thing there. The kids were running around, and they were playing hide and seek. One chubby fellow went and hid behind the couch I was sitting on. I was 16 or so and yelled, "Hey everyone! The fat one's behind the couch!" He immediately got out and asked how much I weighed.
I couldn't really come up with an answer. I was a jerk.
36. ‘Tis the Season to Be Bratty
In high school, me and my goon friends use to go out looking for houses with those inflatable Christmas yard decorations. Just so we could run at them full speed to tackle them like they were tackling dummies. It became our holiday tradition. We must have destroyed the holiday spirit of every suburb neighborhood we ran into in the greater Los Angeles area.
Yet, as a person who now owns holiday decorations and embraces the holiday cheer, I feel like a jerk.
37. See You Next Fall
Back when I was in the third grade, a kid from my school was running in from recess at full speed. I stuck my foot out and tripped him. He slid what seemed like 20 ft. on rough concrete that was dusted with pea gravel. There was no reason for it. He wasn’t mean to me or anything. I just thought it would be funny. It was not.
38. The Song for Future Singledom
I suspected my wife of cheating and had had the feeling for some time, so when she received a late-night text, while she was sleeping, I decided I needed to check her phone. The text was from a known friend and was typical so no big deal, but I chose to scan through previous ones just to...I guess see if there was anything.
I wasn't opening them, just skimming to see if there were any obvious signs. Not too far in, I found a number I didn't recognize and didn't have any name attached. There were all these romantic texts saying things like we never had enough time and stuff like that. I was upset and couldn't decide if I should wake her or confront her the next day after having thought things over.
About an hour or so later, I heard her get up to use the bathroom. Without giving it much thought, I went to her. After a little small talk, I asked her who the heck the number was. She paused and stared at me, and it was then I had my answer. I told her about the texts I found and repeated some of them. I explained why I was going through her phone. And she laughed at me.
She said they were song lyrics she had sent to herself to look up later (this was pre-smartphone) and that I'm a moron for not knowing his own wife's phone number. I pulled my phone out and, sure enough, hers was the number I had found. I was, indeed, a moron. And now a snooping jerk. She kept her phone locked after that, and we happily divorced soon after.
39. Keep the Dirty Business to Yourself
I think about this pretty often honestly. I had to be about seven or eight. I'm in the mall with my mom and sister and it is just about closing time. On our way out of a department store, we stop at the bathroom before the ride home. My mom sends me into the men’s room on my own. Nobody in the bathroom. For some reason, my stupid little brain thinks, "I'm gonna poop on a bunch of paper towels and slap it against the mirror..".
I try to think back to why I would ever have this compulsion, and I got nothing. Having since worked many service jobs over the years, I am profoundly sorry to that custodian.
40. Her Knight in Shining Ego
I used to pull that "nice guy" BS on women all of the time. I would ask a girl out, get rejected, desperately plead my case about how nice I was (even though trying to guilt-trip your way into a date is, in fact, not a nice thing to do at all), then get frustrated and angry when she avoided me and unfriended me on Facebook.
Pretty embarrassing to look back on, but if you can't look back and realize you were a total jerk sometimes, you're probably still a jerk.
41. Have a Little Faith
I was adopted by lovely and caring parents, but throughout my entire childhood and teenage years, I wanted nothing but distance from them for the sole reason that they were religious. They weren't even the fanatic types. They were incredibly tolerant and respectful towards just about anything and anyone. They had the belief that they not only couldn't judge anyone, but also would be punished if they did.
When I was 11, I told them I didn't want to go to church anymore and they accepted it. I mean, I was 11 and they already respected my decision. That just made it all that much harder for us to connect at any level. 90% of everything they did was talk about Jesus and whatnot. In hindsight, I used to be kind of a jerk about it, while they were always perfectly calm and friendly, even when I downright offended them.
I lost both of them in a car accident when I was 18. Now I see that whether someone is religious or not, old or not, male or female or neither, black or white, from your country or a foreigner, being a jerk is just that: being a jerk. Where you come from and your general philosophy of life can't really do much to make it better or worse.
No matter how right you think you are, don't be a jerk!
42. Not the Most Romantic Exit Strategy
My first boyfriend and I started dating in high school. We were absolutely inseparable, as we'd been best friends for years before we started dating. We were there for each other through the loss of a parent and a sibling, and so many firsts. We were going to live in the same dorm in college the next year. A pair, for sure.
Our senior year, I decided I wanted to go to prom with some random guy that I'd developed a crush on during our senior trip. Because we'd been friends so long, I decided that instead of breaking up with him (which felt cold-hearted), I'd soften the blow by just being incredibly mean to him. This way he wouldn't be as upset when I finally told him.
I was HORRIBLE to him for DAYS—just didn't let up. Everything he did was wrong. Nothing was funny. His new haircut was ugly. Why was he so stupid? I finally said something that broke him while we were watching a movie one night and he asked why I was being so awful. I decided that then was the best time to tell him that I was breaking up with him, specifically because I wanted to go to prom with someone else, who I barely knew.
He started sobbing, which my teenage brain could NOT understand. I kept asking why he was so upset, but he wouldn't tell me. It turns out that after years of friendship, I'd blindsided him with the world's cringiest breakup, on his birthday, which I'd completely forgotten. 20 years later, I still wake up in the middle of the night feeling guilty about it.