If you're anything like me, you love hearing other people's embarrassing stories because it reminds you that there are other weirdos out there who are just as awkward as you are. That's why I was so relieved to come across this AskReddit thread asking te question "What's THAT thing that you once said or did, that you still cringe at to this day?" Reddit did not disappoint with its answers.
1. Don't worry, RockRock-. We've all said some weird things to our bosses.
My first big meeting at my job with all the head honchos...and I had to leave to go to a doctors appointment. I was so nervous about walking out of the meeting, I actually said to my boss's boss "good night, I'll miss you!" My boss found it hysterical and told me I turned bright red as I shuffled out the door.
2. the_micked_kettle1's genuinely concerned text is more adorable than cringe-worthy, in my opinion.
I was texting a girl whom I was interested in, and, she was having a shit day. But, she was kind of... standoffish? Anywho, in an effort to find out was bothering her, and maybe brighten her day, I asked the question... the question that will never forget... mostly because my friends won't let me. I asked this girl "what's rockin' around that pretty little noodle of yours?". Not my proudest moment.
3. anghus's tale of unrequited friendship is made better by the fact that they were only in 6th grade. We were all awkward in middle school.
When i was in 6th grade i used to call a girl every night after dinner for like a year. I thought we were best friends. One day at lunch i asked her if i could have some of her M&Ms and she said 'Yes, if you stop calling me'
4. RadioactiveSlothMan's accidental insult is pretty terrible. At least he didn't actually mean to offend anyone.
I was working backstage in a production of The Addams Family (the play.)
I asked the girl playing the old lady if the effects makeup they used to make her teeth look all old and gross had a funny taste.
They hadn't put any makeup on her teeth.
![]()
5. Bet silvermyth's teacher didn't wake up expecting to be talking about weird sex things with his freshman students that day.
We used to have weekly 20 minute "silent reading" sessions during my freshman year of high school, where we brought in a book of our choice. One time, after the 20 mins were up, my teacher had us go up to the whiteboard in turns and write down one word we came across in our reading that we were not familiar with.
I wrote "dominatrix".
Edit: To this day I seriously can't remember what book I was reading. Definitely wasn't anything pornographic.
My teacher did answer! After doing a double take and pausing for like twenty seconds to collect his words lol. He told me it was a "very dominating woman" and left it at that.
Looking back at it, I feel bad for the position I inadvertently put him in. Generally not something any male teacher wants to explain to a 14 year old girl.
6. In deviantsage's defense, no one told her the nickname for people from her town was also a racial slur.
I grew up in a very white, very rural town. When I was in school, people from our town (because of the town name) were frequently referred to as "Beaners". I had ZERO CLUE this was a racial slur, and assumed it was along the lines of being called a "Yankee" as a northerner; not friendly, but not profane.
ANYWAY, a beloved (and coincidentally Latino) faculty member passed away pretty unexpectedly, and I wrote a tribute to his life, which was read at his funeral and published in various places that included the phrase, "For the man who made "Beaner" a compliment".
I meant it in the way that his excellence gave value to our town, with zero irony, and was well into to college before I realized my mistake.
And no, nobody corrected me.
7. Ugh, noooo, ChrisTheB! Why must the box where you type your Facebook statuses look so much like the search bar when you're drunk?
That time I wanted to stalk my crush on FB while I was drunk and ended up spamming my crushes name all over my wall in different spelling variations.
![]()
8. Give drivebyhug a break. How's a homeschooled kid supposed to know the rules of baseball?
I was homeschooled and put into a public school softball team at 13 or so? I had never played games with other kids and wasn't allowed to watch tv so didn't know ANY rules or how the game worked. I just ran around when people yelled and tried to steal the ball from people from time to time. I ran the bases when I was supposed to be at one. I stole home plate. I threw the ball to the outfield Those poor kids probably thought I was disabled.
A few years ago, was walking into a restroom at a movie theater. I thought a man was following me into the restroom mistakenly, so I turned and said "this is the women's bathroom." She responded "I know." I was mortified. She was an older lady. I still feel bad about it to this day.
10. dokiardo has lived a full, beautiful, awkward life.
Wrote a condolence letter to a friend when her siblings both died. I got both names wrong, she opened and read the letters right in front of me.
Had to pee while shopping with my mom at a clothing store. So i pissed in the changing room stall. Mom got an earful from the manager.
I thought in TBall that the cup they had you wear would hold my piss if i had to go. Nothing like having your kid piss himself in outfield.
Was introducing my wife to extended family members at a wedding. When i went to introduce like three of them i all the sudden drew a blank for their names. I just stood there for like twenty seconds going ummmm. I just put my head in my hands and said sorry i have a headache please excuse me, and left my wife there for a few minutes.
I was doing chest compressions on a patient in the hospital. Nurse tripped and pulled my pants and underwear down. She tried for a good 30 secs to pull them back up for me.
So many others. So so many.
I was changing my baby boy. Took his diaper off, lifted his legs to wipe him. All the sudden i heard gurgling. He was peeing into his own mouth. I just stood there for a second perplexed.
![]()
11. AmnesiA_sc's story of a disastrous trip with his girlfriend is long, but well worth the read. There's even a Part 2. Just wait until you get to the part with the blow dryer.
I didn't hit puberty until about 16. Needless to say I was a bit behind in how to deal with the ladies... so I got an internet girlfriend. Got my family to drive 900 miles to visit her for 2 days. A 48 hour cringe is what that trip was. It was so bad that when I was in the military I could get out of trouble with my drill sergeants by telling tales of my awful dating experience.
Take, for starters, the fact that both of our families were meeting at a pizza place. I walked in, saw her, and ran back out of the restaurant and pretended like I didn't see her, I was so scared. Came back in, sat next to her, and was too afraid to make eye contact the entire time. My head was on a 90 degree swivel between my mom straight across from me and the soda machine to the left of me.
You can imagine how the rest of this night went if I spent my first hour trying to work up the courage to look in her general direction. Now, this girl, let's call her Schmessa, worked at an ice cream place. Her broworker had been teasing her that I was only traveling all this way to "get some." So we go to her workplace and first we see a guy that I've talked to before who's pretty cool. He says, "Alright nice to meet you" and tries to do a super cool bro handshake. I try to keep up but I fuck it up about 4 times before he says "Nevermind, nice to meet you" and goes back to work. You can't imagine how embarrassed and scared I was from that alone.
We go into the ice cream place, she orders (because I have to try a malt - turns out it's basically a milkshake idk) and then this guy behind the counter comes over to us and asks me "So did you get some yet?" "Huh?" "Did you get some yet?" "Oh uh no we're good, she just ordered." Fucking idiot. He was asking if I "got some" and here I am thinking he didn't just see us order. He laughs and walks away while she loses what dwindling respect remained for me.
WELL, super. The agenda from here is to go to her house so our families can pow-wow, then we have to check into our hotel room, then Schmessa and I will be going to see a move - any movie. The family stuff is awkward but I get through it without any major incidents that make me feel like my face is melting off. We go to the hotel room to check in and my mom (probably knowing what an abysmal dork I am) has okay'd me to get my own room (score! If I wasn't me, that is). My step dad was unaware and he was hesitant to let me do that, but reluctantly agreed. As luck would have it, my room is on the other side of the hotel from my parents, THE SKY IS THE LIMIT!
So it's time to unpack our stuff, Schmessa comes with me to my room, and just like any horny teenager I... panic and start trying to come up with anything to do. Be funny, be aloof, be random, do something quirky. I'm a mess, I hate to even admit this. All I can come up with is to get really excited about the hair dryer. Jesus fucking christ, it's been almost 10 years and I still cringe about this. I yell out to her about how great the hair dryer is, she should come look I'm dumping water on the counter and this amazing stupid fucking hairdryer is drying it up SO fast. I can't possibly relate to you how bad I hate myself for this.
Mission success, I've wasted enough time that it's time for us to leave for the movie. Being the inner-neckbeard I am, I brought a sweatshirt along; not because I need it but because if she happens to get cold what a suave hero I'll be when I say "Here take mine." We get to the movies and as if on cue she says "Hmm, I'm kind of chilly." Well it's about this time I notice that I have forgotten the sweatshirt in my parents car. I could have pulled her close to keep her warm or even "Not really, maybe you're just a pussy," would've gone over better than "Fuck, I brought a sweatshirt exactly for this occasion!" "It's fine!" "No, god how dumb I don't even need the sweatshirt I was going to bring it for you but I left it in my mom's car!"
The fact that I wasn't struck dead by lightning that moment is proof that God is not merciful. As we're nearing the ticket counter I realize that I have no idea how to buy a movie ticket. I've done it before but I never thought about it and now that I'm thinking about it, I have no idea what I normally do. "Two for Ocean's [Number], please" sounds right but is it too cliche? Do people actually say that or is that just on Happy Days? What else would you say? Time's up, we're there, I have to use the only phrase I can think of. It actually goes really well, my message gets across and the guy gives us our tickets without any weird looks. Thank God she didn't want snacks, that would've been impossible to get through.
I don't think I have enough space to get into what disgusting mess happened inside the theater right now, or the awkward body pretzel I invented to avoid kissing her the next day at the zoo, but trust me that it doesn't get much better from here. The fact that I remember this so vividly after 10 years is testament to just how catastrophic this trip was.
![]()
