Nobody's perfect. Almost everyone has had a moment where they made a rude comment or acted like a bully, whether it was to make a joke, fit in with the cool kids, or vent personal frustrations. What's important is the ability to be able to reflect on bad behavior, recognize the wrong, and change for the better. These people share their most regrettable moments in which they were the bad guy and how they've changed from that event now.
All content has been edited for clarity.
They Didn’t Realize His Situation
“Mine was definitely the time my friends and I bullied the new kid on the block. It was nothing physical, but we made fun of him and excluded him for not having a scooter. Then one day he showed up with a new scooter, and we bullied him for having a cheap one.
Years later, it became apparent that his family wasn’t as well off as ours. None of us realized we were picking on the poor kid, and when the family bought him the trendy toy, it just wasn’t good enough for us. We were so mean to him and I feel awful about it. Sorry, Omar.”
Now That’s Pretty Cruel
“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 death 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 my boyfriend (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 worst breakup, on his birthday, which I’d completely forgotten. Twenty years later, I still wake up in the middle of the night feeling guilty about it.
We did end up living in the same dorm freshman year, and managed to remain friends for a couple of years before falling completely out of touch. I don’t think I realized quite how horrible I’d been until I finally ended up on the other side of it and by then it was too late, by years. I try to look him up every now and then but don’t have much luck. I kind of feel like an apology at this point would be more selfish than helpful.”
The Wrong Way To Leave A Tip
“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 the plates. I 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.”
He Became Who He Hated The Most
“I had dated a few girls in high school but nothing really came out of it. But I had a lot of female friends. They would talk to me about their problems, home life, boyfriends, etc…and I always gave them a safe space to come to.
Enter college, and I develop much of the same with a new group of people. I guess it’s my thing. So I get invited to this party by a few of them and meet this absolute stunner. She is totally out of my league. But worse than that, she was always hanging around jerks. Just conceited jocks who think the world revolves around them and their privilege and she is their cheerleader. Great. Nice going, girl.
After a few times meeting her and talking to her (just general party talk, nothing deep and earth-shattering) she asks me out to dinner. Huh, ok, I’ll see where this goes. Well, we start dating. Sweet, here she is, the centerpiece of any guy’s collection, and she’s with me. Because of who she is, I don’t really get too close to her. When we want to get together for a little fun, it’s on, but otherwise I have my friends and such to spend time with.
After a while, it runs its course. It was great of course, and having her on my arm was an ego boost like none other, but there was really no depth there so it just kind of played out. We break up and go our separate ways and that was the end of it. So I thought.
Years later, I end up back in the area at a friend’s wedding. She is at the hotel, but working a different event. We get to talking afterward and bring up our college days. She says something to the effect of ‘You really were different from what I had expected.’ I press on a bit to see what she meant, and I find out the following: she had a habit of dating conceited guys because they were the only ones who would approach her. She saw me with my friends and figured I was different than the jerks she was used to. She talked to my friends about me, and they told her how sweet, caring, sensitive, and funny I was, and that she should definitely go for it. So she came looking for someone who would appreciate her for the person she was, and I had judged her by her company and became the same jerk as the people I resented.
I don’t remember much of the rest of that night or that week because I spent it reliving every horrible event. Every moment I dismissed her. Times I ignored her. Days I spent away from her. We didn’t have much in common because I hardly ever talked to her about anything. I had judged her for being with the worst boyfriends ever…then became one of them.”
Yeah, Those Weren’t Vampires
“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.
It explained why everyone was giving me weird looks for being dressed up as a cowboy.”
A Compulsion He Never Understood
“I think about this pretty often honestly. I had to be about 7 or 8 at the mall with my mom and sister, and it was just about closing time. On our way out of a department store, we stopped at the restroom before the ride home. My mom sent me into the men’s room on my own. Nobody was in the bathroom. For some reason my stupid little brain thought, ‘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.”
Justifiable, But Maybe Not The Nicest
“In my very slight defense, my boyfriend at the time in high school had 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 found her sobbing so hard in the bathroom that nobody could even understand what she was saying at first. So he was a jerk too, BUT then there was me.
My dude was stupid, like genuinely very dumb. He was the typical football jock who’d been socially promoted probably since kindergarten, and could 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 were just plain awful. 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 slept with and dumped my little French friend, I SHOULD have dumped him with a big lecture on statutory assault. 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, I 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 getting back at 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 stinks 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. I didn’t even make him understand in his tiny brain that what he did was wrong. And honestly, football jocks get a near-pass on that kind of predation, so he definitely needed to hear it. I took the petty way out that I knew would hurt him the most, instead of being an intelligent near-grownup and giving him an earful in the way that he actually deserved.”
“It’s Messed Me Up Irreversibly”
“I dated my best friend’s ex-girlfriend. It was the actual worst year of my life.
He was just sad and confused. I chose to date her at a very hard time in his life and me doing that only made it harder for him.
My friend told me a lot about her and how she was during their relationship right before we stopped being friends. Of course, I didn’t take what he said seriously because at that time she was feeding me lies about him. Turns out everything he told me was right. She was manipulative, extremely selfish, a drama magnet, and emotionally and physically abusive. Basically everything bad you can have in a relationship.
About a month or so after, she and I broke up, he started messaging and commenting on my social media and one day he asked to hang out. We both just missed each other and chose to forget about that whole thing. And whenever it was brought up, we’d just joke about how dumb we both were for dating her. Our friendship was never exactly the way it was before, but it was as close as it could get to the way it used to be. I love the guy to death.
It was my biggest regret for a long time, but it taught me a lot about relationships and friendships. However, it’s still a struggle to try to forgive myself for it even after my friend forgave me. It’s messed me up irreversibly.”
“Don’t Be A Jerk”
“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 the much harder for us to connect at any level. About 90% of everything they did was to 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!”
That Joke Fell Flat
“There’s this one time about a ‘joke’ I made in high school that I’ll never forget. I had a HUGE crush on this guy I’d never spoken to. In one class, his seat got reassigned to the seat next to mine, and I think I died of happiness. He asked for my name and then started singing a silly song he made up using it.
So my smitten self decided to make a joke about it, except I’m incredibly socially awkward, so instead of a flirtatious smile, I pinned him with an irritated stare and said, ‘I can already tell you’re going to be annoying.’ He shut up immediately, looking very put off, and we never spoke again. I still die a little inside every time I think about it.
In retrospect, if I could go back and apologize, I would. It’s definitely one of those lie awake at night and cringe about all the ways you messed up moments.”
She Didn’t Want That Tip
“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 criticism of the job she did until my dad explained that to me.”
A Taste Of Their Own Medicine
“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.
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 that 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 and the security guard had no idea I was video taping him as he ushered us out. We thought it was hilarious and unfair that we were being kicked out for having a little fun.
Fast forward to 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 cow, we were being such jerks.’ We had definitely knocked over quite a bit of displays that day, which was part of the reason they had security guards take us out. We were probably such a huge pain in the rear to a lot of people that day, but we just didn’t see it that way because we were dumb teenagers.”
Who Was The Bully Here?
“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 the eighth grade, they were pretty much okay, but I still carried a lot of that trauma.
In the eighth grade, a girl in my class, who was not part of the bully group but 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 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 had gotten over a lot of my misgivings about people. She explained that she had felt so bad about what had gone on with me and her friend group, 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 a reminder that 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.”
He Could’ve Asked
“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 I have no silverware. For some reason this annoys me. There is no silverware set out on the tables I can grab, and 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 waited.
About 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 ticked off tone you would imagine.
She apologizes and offers to go get silverware, but I tell her it’s cold now and I have to get back to work. I pay my bill, leave no tip and walk out.
But there was no reason for me to be a jerk. I apologized to her over and over again afterwards. 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.”
The Biggest Cringe
“My best friend and I have a gif we send 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. I’m pretty sure she doesn’t remember, but I’ll never forget.”