People Share The Poorly Chosen Words They Said Years Ago They Still Regret

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We’ve all said things that we didn’t mean. Most of the time, we are able to learn from our mistakes and move on, knowing better for the next time. But in some cases, the words that left our lips were just so poorly chosen that we still regret them years after we said them. Even in moments where our words may have unintentionally offended someone and were forgiven for it, we still stay up most nights wishing we hadn’t said anything in the first place. People from across the globe took to the internet to share moments where their poorly chosen words still kept them shaking their heads in regret years after. Read on for some cringe-worthy (but equally insightful) tales.

#1 So Close

In seventh grade, a cute girl asked me to sit next to her. I said my mom won’t let me sit next to girls. My mom said no such thing. If I had said CUTE girls, I would have been a total baller. So close.

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#2 Unintentional Burn

I was in fifth grade or so and I was sitting in class with a couple of classmates. We were talking about Weird Al songs we liked. This one girl asked, “Have you heard ‘Eat It?'” and I followed with, “Have you ever heard ‘I’m So Sick of You?'” Which I guess they hadn’t heard because she looked immediately down at the desk, sort of somber. Some dude even did a little, “Hoo-hoo” as if I did a nice burn. I guess they thought I was telling this girl I was actually sick of her… I had no clue at the time though, so I just let it ride. I still feel bad about that one.

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#3 Peer Pressure

In seventh grade, I was at the mall with my brother and a girl from class asked me: “What would you do if I kissed you?” and my brother said, “Die.” I repeated his answer, saying, ” Yeah, die.” She rightfully slapped me and stormed off. I felt like such a jerk… I actually liked her. I was just embarrassed and tried to seem cool to my older brother. I still feel bad about that, thirty-something years later. She must’ve forgiven me because we stayed friends after, but I regret making her feel bad. Kids suck, haha.

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#4 What Are The Chances?

I accidentally mixed up an inside joke with the wrong friend group with disastrous results.

Friend group #1: The “joke” was that when someone called and asked who was there, we would add Darrell to the list of names. Darrell wasn’t a real person. The joke wasn’t really funny and made no sense out of context, but I guess that’s why it was an inside joke.

Friend group #2: I was hanging out playing some drinking games with a bunch of people that I hadn’t hung out with for a while. It was a kind of get together to remember their friend who had recently passed away in a car accident. I didn’t know him that well, but I was always down to party.

Anyway, the phone rang, and the person who answered started listing off names. Sorting my cards for another round of Presidents and Jerks, I offhandedly said, “Heh, and Darrell!”

It was the typical record scratch moment where everyone stopped and looked at me. Darrell was the name of the friend who had just passed away.

This happened in 2002 and I still think about it all the time.

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#5 “Let Me Explain”

Oh man, I have a mixed-up inside joke scenario. It wasn’t me, it was my neighbor.

My neighbor is morbidly obese and my mom is Korean. They joke with each other about it. My neighbor makes racist commits to my mom, and in turn, she makes fun of my neighbor’s weight. It’s just part of their friendship. They often did it in public too, but it was always obvious when they were standing next to each other that it was inside joke.

At one point, my neighbor was out with her husband (they’re both white). She was at a check out counter when she blithely remarked about all the damn Koreans taking over the region.

The check out lady just stares at her. Then the husband leaned over and said: “It’s not as funny when his mom isn’t standing next to you.”

Cue my horrified neighbor desperately trying to explain that she wasn’t a racist, that it was an inside joke. “My friend is Korean!” which of course just made her look worse.

My mom lost it when she heard the story.

#6 Bad Timing

I once said a “Yo mama” joke to someone whose mother had just passed away.

He was actually really classy about it. I cringe each time I think of it.

#7 Scarred For Life

When I was in fifth grade, our teacher said a joke in front of the class and everyone laughed including myself. After the laughter died down, a girl looked up at me and said. “You have a really disgusting laugh, ew.” I became so self-conscious about laughter since that specific, day, and after many years I still have trouble laughing. My brain kind of made it a habit to just smile or slightly chuckle at something, even if it is really funny.

#8 Rude Remark

When I was in seventh grade, I had such a hard time in school. No self-esteem at all. The one friend I had was a very pretty girl and she was so nice. Well, we were sitting in class and laughing at some joke she told me. I would always cover my mouth when I laughed but I didn’t that time because I was genuinely happy.

The guy next to her turned to me and looked at me with such disgust I can’t forget it 10+ years later. He said, “You look like a man when you smile.” I think of that to this day and it hurts like no other. I have never been comfortable with my smile, and always feel like I do look manly. It sucks.

#9 Harry Potter Drama

I went through a phase where I scolded people for reading Harry Potter because my parents told me it was evil. Lots of awkward situations because of that.

#10 Self-Righteous Jerk

My parents were ultra-religious and taught me to have a really messed concept of men, love, and relationships. When I was in middle school, I scolded so many of my friends for having crushes or getting boyfriends. I remember I lost one friend because I told her that it was disrespectful of her to have a boyfriend while also having a crush on Michael Buble. I equated her crush on Buble to being as bad as cheating. I always cringe and facepalm whenever I remember how much of a self-righteous jerk I was. I totally deserved to be friend-dumped.

#11 Word Vomit

Junior prom. During dinner, I blurted out to my date: “I’m so bored.” I have NO idea why it came out of my mouth. I’m pretty well-mannered and quiet. I forget how I tried to play it off, but I felt so bad.

#12 A Spaced Out Answer

When I was 11, it was my first day at a new school and all the other students were also new. The math teacher started our first class by asking each of us about our educational background (what school we came from, what they taught in our last year’s math class, etc.), just trying to get a general idea of what kind of students he was dealing with.

The thing is, I was so nervous that I spaced out for a bit and got lost in my overthinking, so I didn’t hear the teacher’s questions to my classmates. When it got to my turn, the teacher just said “Now tell me about you,” assuming I understood what kind of information he was expecting. I just went straight into a monologue that started with “So I was born in the South Zone of the city, but my mom decided to move to our current neighborhood a few months after divorcing my dad…” And went on and on giving some very specific details about my short life.

Everyone had a really confused look on their faces and as soon as I realized the teacher was also completely lost I stopped talking and went instantly red. The teacher then said, “That’s all really great, but I was only interested in what happened last year, not the last 10…” and everyone started laughing. The next day, nobody remembered it anymore, but 12 years later it still comes to mind in pretty random moments.

#13 A Huge Regret

For most of my education, I went to public school. Like most kids, I was socially awkward. In high school, I received an academic scholarship to a private Catholic school. it was a really big deal for my family. I didn’t know anyone at the new school. Between an odd combination of academics, sports and the tail end of puberty, I became very popular in this new school. I wasn’t used to the attention and it definitely got to my teenage head. Nearly all of my social circles were formed in the new school and not with my old local friends.

One day in junior year, I headed to a McDonalds for lunch with a few friends from the new school. I saw a girl at the counter who I used to go to public school with that I used to have a crush on. She just lit up when she saw me—she was so excited, and I … I was a terrible teenager who just ignored her. I pretended I didn’t recognize her. She looked so deflated when I didn’t acknowledge her.

Note that this was the 90s. My family moved a few times after that. I settled down in a different part of the country after university. I never made it back to that town. I’ve relived that jerk moment for years now. Fast forward to one of those nights when I relived that moment, and I decided to look her up on Facebook to apologize. I find out she passed away 10 years ago in a car accident. Since I found out about her fate, I feel even more awful about that moment.

#14 Awkward Handshake

Freshman year of high school. It was one of those days before school started and you met your teacher. My parents were there. My teacher was handing me a piece of paper but I didn’t see it, so I shook his hand. He said, “Oh” and my mom said, “Umm?” I panicked and said, “I just wanted to be polite!”

#15 Bad Teacher

I can’t even begin to pinpoint one event. I guess one thing is when I was 11, I asked my teacher if I could go to the bathroom three times during class and she told me no. Sure enough, I couldn’t hold it any longer and boom, I endured bullying for the next six months. It literally shakes me in bed about how I have never felt that low before. SOMEHOW I managed to live through it though. We all got flaws.

#16 Sleeping On The Shift

A co-worker of mine was fired recently for falling asleep on the toilet. He was caught because he was snoring. I was asked a month or two before that to see if he was wasting time on the internet (I’m the IT guy) because his work wasn’t getting done. In the adult world, you can use the bathroom as long as your work gets done, but if you use it as an excuse to dodge work, you simply lose your job. You don’t get fired from the school.

#17 Cringeworthy Admission

I always physically cringe when I remember I told my crush in ninth grade I liked her because I thought she liked me too. After some reflection, I realized it was basic kindness.

#18 The Worst Song Choice

I was visiting Portland for a wedding that lined up with my birthday as well. We went out to celebrate and finished the night at a karaoke bar. Realizing I was too tipsy to sing, I picked “My Name Is” by Eminem as my song to perform. There are two versions of that song. One is the original release, and the other is a tamed down version (which you most commonly hear today).

The woman controlling the music put on the original, and off I went. One of the lines at the end is: “Running over LGBTQ in a spaceship while they screamin’ at me, let’s just be friends.” I finished the song and I was met by applause from my friends and one other table. The rest of the place was silent. The DJ said, “Nice job! I don’t know if it was the best choice for gay women’s night though.” And at that moment I wanted to leave my skin.

#19 Embarrassing Party Trick

My party trick in high school was that I could rap the fast part of Rap God. When I was a freshman in college, I was hanging out with my friends one night, and we were all pretty tipsy but I was probably the most wasted. So I decided to bust out my old party trick: “Hey guys, turn on Rap God!” Somewhere out there is a video of me lying wasted on the floor of a dorm room, rapping Rap God as fast as my tipsy little mouth could go. Chloe, if you’re reading this, can you delete that video for me?

#20 Chasing Girls In Buses

This happened back when I was sixth or seventh grade. I was with a couple of friends browsing the neighborhood after the school day was over. We happened on a bus stop with a couple of girls seemingly our age. We stopped and tried to chat them up, but their bus came soon after and they had to go. We saw their bus stop at a traffic light not 20 meters away and one of us said, “Let’s run to the next stop.” Nobody thought to ask, “Then what?” We just went off, sprinting madly behind the bus.

Surprisingly enough, we somehow made it to the next stop just as the bus was arriving. Then the doors opened, and the girls sat there giggling. We did nothing. Literally nothing. I even remember the bus driver holding the doors a bit longer. We just sat there, trying to catch our breaths as my lungs burned. And then the doors closed and the bus went off to the next stop. None of us said anything. We just walked it off and went on to the next stupid things we usually did. I don’t know about any of the other guys, but this still haunts me as one of the cringiest moments of my life so far.

#21 An Innocent Joke

When I was in the fourth grade, I lived in the middle of nowhere and there was practically no minorities, just white county people. This Mexican family had just moved in and could barely speak any English. I befriended one of the kids my age in school. He came over to my place and we were both joking around about his bad English. Just doing what kids do. I would pretend to speak with his accent and then he would copy and it was silly, stupid and innocent. My mom told me I was being really inconsiderate making fun of someone for not being able to speak English. I felt terrible. The next day at school, my friend came up to me and started joking with me again, but I just shook my head and looked down at my desk in embarrassment. He had no idea what was wrong and I was too young and dumb to be able to explain my behavior to him.

As I grew older, I spent probably 20 years thinking about that day and how much of a jerk I was to be friendly one day and then just stop talking to him out without explanation. I felt really bad about it for a long time and often laid awake at night thinking about it. I ended up finding him on Facebook about a year ago and we friended each other. I told him how bad I felt about it and apologized. He just laughed it off and said it was no big deal—he was still really thankful to find someone as friendly as me when he didn’t know anyone here. He said he figured my mom had said something to me about it and it never bothered him.

I don’t know if maybe he was just being nice to me or not, but it was such a relief to hear it. It really felt like a weight had been lifted off of me.

#22 The Dreaded Jacket

In seventh grade, I started watching more anime on Toonami. One day, we had to do a paper describing our summer break and the class had to put a person to a description. I named my favorite jacket that I wore every day “Takeshi,” so I wrote that in my description. The cutest new girl in the class read my description out loud, then said: “What weirdo names their jacket?”

Once no one guessed who it was, I piped up and said: “Well maybe they aren’t here today?” My dumb self forgot though that this was an IN-CLASS ASSIGNMENT. And the teacher said, “No, it had to have been written by someone here?” Finally one of my friends says, “Hey, aren’t you like, the only one who wears that jacket?”

I sunk in my seat as we moved on to the next description… I wake up sweating feeling that jacket still on my shoulders…

#23 Valentine’s Day Confession

I was in the fourth grade and it was Valentine’s Day. I was the new kid in school and this one boy had been picking on me all year. My 10-year-old self was very non-confrontational, so I wrote a paragraph on the back of his Valentine explaining that I didn’t like it when he was mean to me. He couldn’t read my handwriting and brought it to the teacher who made me read it aloud to both of them. I think about that day every day of my life. He even ended up finding me online and contacting me to apologize a few years ago, but all I can think of is the cringe.

#24 Oops…

I was discussing a recent surgery I had at work to a bunch of people, including a lady with spina bifida who lives in a wheelchair. I specifically was talking about how annoyed I was by not being able to walk for 3 weeks. I revisit that one a lot.

#25 Incomplete Description

When I was six years old, my teacher asked us what our parents did for a living. I said my mom did the dishes. After five minutes of explaining what she did at home, my teacher just assumed my mom was a housewife. In reality, my mom was a chemistry teacher, and I told her that I said that when I was 12. You really can’t blame me—I didn’t really think about where my mom went during her work hours, I just knew she went somewhere.

#26 Passing Gas

In eighth grade, I farted once, and a few minutes later, someone smelled it and asked who did it. They asked if it was me and I just started crying. I used to be very sensitive, so I thought they were accusing me and I felt really bad. It’s partially because of that moment that I am now much less emotional, and tend to keep my emotions bottled up.

#27 Not Smooth

I was visiting my cousin about four months ago and we didn’t have the same greeting handshake. So it was like that really weird thing with your hands where you end up in some super awkward handshake. Last night I thought about this like 20 minutes and blamed myself. Man, that was super unnecessary.

#28 “Frank Fart”

Fourth-grade classroom: we were having a face-off between students on who could name the capital of whichever state our teacher named. I had been on a roll getting a few correct in a row. Then the teacher said, “Kentucky.” With all of the enthusiasm (and seriousness) in the world, I screamed, “FRANK FART” Everyone was dying laughing except for me, at the time. Looking back, it cracks me up that I was so upset about it.

#29 Best Friend To Nothing

I was around 15 and having a complete breakdown of all aspects of life. My mother had passed away suddenly, I had untreated mental illness and no one was listening. My dad was understandably a wreck, and school fell to the wayside. I was barely going and intending on dropping out. I couldn’t do anything.

There was a high school dance. I was desperate to have some fun and pretty much have this be the highlight before I left. Though I failed at communicating this. I really wanted a friend to dance with me and our other friends. She was awkwardly sitting alone. I pushed her too hard and made her cry. I couldn’t see through my own issues to see how bad of a position I put her in. All I could see was my world collapsing.

We never spoke again. She went from my best friend to nothing in one night. That was 15 years ago and I still feel awful. Hindsight is always 20/20 as they say.

#30 Living With ADHD

I have ADHD and this is basically my life. If I had a dollar for every time I ran my mouth before my brain thought better of it, I wouldn’t need to work anymore. And nighttime brain loves to dwell on each and every one.

#31 Revealing His Secret

When I was fourteen, my friend and I found our favorite English teacher’s Facebook account and found out that he was a pretty big drinker. My friend told everyone about this and we both got detention the whole week because of it. The worst thing wasn’t the detention, it was the fact that the teacher no longer liked us and he put less effort in his class—making us mostly do book work.

#32 Yearbook Truths

I often lie in bed thinking about an obnoxious thing from Grade 9 I wrote in someone’s school yearbook. I essentially confessed my love for this girl who I never spoke a word to in high school. I’m 38 years old.

#33 Flipping Off A Crush

A couple of years ago I was at the drive-thru window at my bank. When the transaction was finished, I started to raise my hand to wave goodbye to the teller, but instead of waving, I started to flip him off! It happened completely subconsciously. I don’t think I was able to stop it in time because he had a shocked look on his face. I eventually apologized but I still feel horrible shame over it. Every time I see him, the shame comes back. Plus, now I have a crush on him.

#34 Creepy Gesture

Last year I saw a four-year-old kid with his father. The kid wanted to go to somewhere but the father wanted to go home, so the kid started crying. He started running away and the father was calling him to return. My dumb self said to the father: “If you want, I’ll go get him for you.” A woman overheard me say that and started laughing, then the father with a confused face said, “No… Thanks.”

#35 Wedding Day Blunder

When I walked down the aisle at my wedding, I was so nervous and focused on not tripping, that I did not acknowledge my dad. I didn’t realize this until I saw the video my aunt had made for me. You can see my dad lean in to give me a kiss on the cheek but I just keep walking. He kind of shrugged and then went to sit down. It’s been 18 years and this still flashes through my head when I’m trying to fall asleep.

#36 My Sister’s Boyfriend

I stole my sister’s boyfriend when I was 16. I’m not proud of it and she’s still mad at me. Also, he was eight years older than me. Thought that was important to mention.

#37 Endless Overthinking

I’ve been overthinking everything I’ve ever said or ever done… Now, my brain’s trapped in a web that my head has spun! I still think about when I said, “You too” to the delivery man when he said, “Enjoy your pizza.”

#38 Haunted By Dairy Queen

I went to Dairy Queen with my daughter. She brought along her kitten. The cute girl at the walk-up window asked my daughter what the kitten’s name was. “Princess” was the response. Smiling and feebly attempting to make conversation, I said, “Today,” to indicate that my daughter changed the cat’s name frequently.

I got a dirty look and the girl left the window to go make whatever cold treat we had ordered. It wasn’t until later, on the walk home, that I realized that she thought I was telling her to hurry the hell up and make my order. Still haunts me years later for some reason.

#39 Threw Under The Bus

One instance I can remember off the top of my head was in middle school. This girl I was friends with came up to me in between classes in the hallway. I thought she was going to say hi, but instead, she slapped me HARD. She told me I was a two-faced witch, and that my constant happy attitude was disgusting.

I wish I would have done more than just stand there, frozen.

Turned out, some other girl threw me under the bus for something she herself did. This kind of thing happened multiple times throughout school. I stopped smiling after that.

#40 Total Jerk Move

A girl my buddy had given my number to wouldn’t leave me alone. She would call at every hour, follow me in the halls, constantly try to sit with me at lunch, etc. I blocked her number and avoided her at all costs. One day at lunch, she saw me and made a beeline right for the seat beside me. I was with all my buddies and she stood there looking at me, waiting for me to ask her to sit down.

Instead, the first thing to pop into my head was to grab a quarter in my pocket, stand up, show it to her, and at the top of my voice yell, “HERE’S A QUARTER, GO BUY YOURSELF SOME FRIENDS!” I then bounced it off the table at her and it hit her square in the forehead. All she did was stand there while the entire lunchroom exploded in laughter.

She ran out with tears streaming down her face. I calmly sat down and continued eating. It was so out of character for me (I was a skinny, introverted band nerd) that it was the talk of the school for weeks about how brutal that was. I still think about it and it’s been 25 years.

#41 Poor Girl

The teacher was being nasty and said she should have gone to the washroom after lunch. Well, if you’re one of the last kids in the lunch line, you have much less time to eat and no time to use the bathroom. One poor girl ended up wetting her pants and she was so embarrassed. My heart broke for her. Then, this teacher sent her to the nurse’s office to call her parents for clean clothes. No one was home, so she had to stay that way for the next few hours and ride the bus home that way.

What really is frustrating is after the teacher sent her to the nurse’s office, she told all of us to line up because we were all now going to use the bathroom and she didn’t want to hear anyone say they didn’t have to go. Apparently, that wasn’t an option. I don’t remember the girl ever being bullied or picked on for it. I think everyone felt compassion for her. I was bullied in school and it messes you up! I just don’t understand people sometimes.

#42 Feline Fantasy

In middle school,  I had a bigger vocabulary than most of the other kids, and I’d just discovered the word “feline.” We were talking about what it’d be like to transform into animals, and I wanted to say that it’d be cool to turn into a feline because I loved cats. What came out was: “I really want to turn into a female!”

#43 A Hand On The Hip

I was at a friends wedding and ran into another friends mother. She leaned in for the awkward “Hi, I haven’t seen you in a while” cheek kiss thing, and I didn’t know what to do with my hand. I accidentally put it on her hip during this encounter, which probably was nothing. I’m sure it was nothing. I was sure she knew that if it was creepy it was unintentional… I’m sure of it…

#44 A Kitty Pet Peeve

My eighth-grade advanced math teacher had us fill out a “Get to know you” sheet on the first day of school. It asked what our biggest pet peeve was. I didn’t know what pet peeve meant, so I put cats since I thought pet peeves were things you loved. Her room was decorated with kitten posters and she was a huge cat lady. She never liked me.

#45 Church Kid Antics

I was at church in the kid’s service and they always picked a kid to participate. They’d usually get a prize after. That day, they chose by asking us why we should get to go up and I literally said: “My aunt works here, so I deserve it.” I was an entitled little brat. Every time I remember it, I die a little inside.

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