Nobody’s perfect, but some embarrassing mistakes are way worse than others. Sometimes, we say or do the exact wrong thing, or else just make a complete fool of ourselves in the complete wrong situation. Whatever the faux-pas, these Redditors have first-hand experience with embarrassment, and there’s no coming back from this kind of cringe.
1. Splashing Around
I was sleeping over at a girlfriend’s house, and in the middle of the night, I needed to take a leak. So, I got up, went about my business, and went back to bed. In the morning, I woke up to a horrifying sight. The person was not my girlfriend, it was a slender older man. I was extremely confused and I looked out the doorway to see her standing there signaling me out. Yup. I slept with my girlfriend’s dad.
2. Basket Case
When I triumphantly scored in a basketball game when I was eight in front of a whole crowd—only to realize it was on the wrong hoop. I have considered asking my sister to formally sign a non-disclosure agreement.
3. That Doesn’t Mean What You Think It Means
When I was young, I didn’t know the difference between “getting laid” and “getting laid off.” Had no idea that these things are completely different, and I would use them almost interchangeably. So, when my dad lost his job one year, the next day at school I went around explaining to all my classmates: “Yeah, things aren’t going well at my house, my dad got laid yesterday.”
4. Nip It in the Bud
This is funny now that I think of it, but at the time it happened it was quite embarrassing. I was put in the cheerleading class by mistake at the beginning of tenth grade. It was glorious at first, because I was the only guy in the middle of 20+ beautiful girls, all in tights, dancing around me. However, I started getting bored just sitting in a corner all class till the bell rang…
So I started playing with my left nipple for some reason without even noticing—till I saw like five of those beautiful girls looking at me and laughing. Then it hit me. I was holding my nipples with the tips of my fingers.
5. It Runs in the Family
Was at a friend’s brother’s 21st birthday party and was standing around talking with some other guys. On the driveway, a bunch of girls were dancing to the music. It was a really chill night. But it was about to get a lot chillier. I said to the guy on my other side, “How about the rack on that blonde chick?” He replied, “That’s my daughter.”
6. What’s the Difference?
When I was seven years old, I saw thongs at Victoria’s Secret. I wanted one but my mom was like, “No, they’re for adults.” That same day I was in my room and got a pair of my underwear and cut them so they would look like a thong. I put them on and started modelling them in front of the mirror. My mom opened the door and saw what I was doing. She just looked at me shook her head and walked out.
7. A Robe and a Wink
I was in the middle of changing one morning and realized I didn’t have my shirt and bra. So, topless, I ran down into the basement to get them off the drying rack. Big mistake. My sister and her boyfriend had apparently gotten into a fight, because there he was, lying on the floor but waking up. Remember, I’m COMPLETELY topless.
I pulled the, “Maybe if I’m really quiet, he won’t notice I’m here.” After successfully getting through the door to my laundry freedom, I get a robe and a wink for Christmas about a month later. Fail.
8. The Piano Bar
A couple of years ago, I was at a popular piano bar with my friend for her birthday. We were sitting in the very front by the pianos and there were about 200 people in the bar at the time. I went to the restroom and when I came back, the piano players called me over. I danced with them and my backside was facing the audience. I thought I looked hot, but…
When I sat down these two random women come over to me. They said the worst thing possible: “Your dress is tucked into your underpants.” I had been dancing with my bum hanging out the whole time.
9. Did I Do That?
When I was writing the SAT, I finished a section early, and because it was an early morning test, I decided to take a quick 15-minute nap before the next section. While semi-asleep, I tooted and startled myself awake in a silent classroom, surrounded by 20 kids from my school. Looks of shock and terror, as well as muffled laughter, quickly filled the room. There was still over an hour to go in the test.
10. Siri, Let the Earth Swallow Me
I got my first iPhone about 7 or 8 years ago, and it was the first to have Siri. I was listening to a lot of hip hop at the time, and the phrase I chose to say to Siri was “I love it when you call me Big Papa” like the Notorious BIG song. Siri asked me if I wanted her to call me Big Papa. Why the heck not, I thought.
So this event totally left my memory until about two years later, when iI was looking for an email I had sent from my phone. I found it, and was horrified to learn that it had been signed off from “Big Papa.” Everything I had sent from my phone in those two years, including job related emails and even applications, had been signed off from “Big Papa.”
11. Mom’s Wand
My mom caught me playing Dungeons and Dragons this one time. Fine, whatever. But what I was holding made it the worst situation ever. I was a ten-year-old wood elf archmage, wielding the “wand” that I found tucked under mommy’s bed. I think you can guess what that wand actually was. My mom was absolutely mortified.
12. Kiss and Tell
Back when I was young and before YouTube, I looked up “How to Kiss” on the Internet. It was a Yahoo answers page that usually came up. There wasn’t much useful information, it was all “just do what comes naturally,” but the idea of kissing was unnatural to me at the time. When I finally came to my first kiss…I screwed it up so bad.
I spent so much time trying to process everything I had read and put it into my mouth and tongue that I sort of just became completely and utterly frozen for the entire time. She was trying to do something fun and I was just “WHERE DOES MY MOUTH GO IF SHE GOES LEFT HELP ME INTERNET” But the Internet couldn’t help.
13. It’s the Little Things
I scored an interview for a dream job. I did all of my research about the company, bought a new suit, the whole shebang. I gave the man interviewing me a firm handshake, answered all of his questions easily, and felt pretty confident. After finishing the otherwise flawless interview, we shook hands again, and I said, “Thank you sir.” To my horror, she replied: “It’s Ma’am.”
14. Good Grief
My mother and I were out walking and we came across an older couple we knew from the local church. Their eldest son had died the previous year from an inoperable brain tumor, and their younger son just moved out for university. Mum starts with, “Must be nice to have the house to yourself! More time for Church!”
The conversation devolves from there. She ignores all hints to drop the subject, including the mother stating they hadn’t been back to the church since their son died. The couple were obviously horrified. I couldn’t end the convo quick enough. Afterward, my mother told me I was just being immature and had no conception of what “polite adult conversation” was like.
15. He Knows If You’ve Been Bad or Good
Around Christmas when I was seven, I was watching a movie with my parents and heard the characters talk about adult movies and such, if you catch my drift. I asked my parents what it meant, and they didn’t tell me, so I looked it up on our family computer. Well, once I saw what it was, I got terrified I wouldn’t get anything for Christmas from Santa.
So I wrote a letter to him apologizing. He wrote me back and said it was ok. The next year, I realized Santa was my parents. It still keeps me up at night.
16. Here’s the Scoop
When I was about four years old, I liked to be naked a lot in my house. I don’t know why, but I had an ice cream scooper, the kind with a wire on it, and for some reason I had it around my “private area.” I was pushing the trigger on it, and my junk got caught into it. I was screaming, and it wouldn’t come off.
Apparently, I had also recently watched the movie Independence Day. Remember that scene where the alien has a hold of that guy and he keeps saying “Releeeeaaaassseee meeeeeeeee”? I kept saying that over and over again in the same tone. My mom finally saw and helped get it off. My parents tell this story all the time, and I still get anxiety whenever I see an ice cream scooper. My wife also bought me one for my birthday as a joke.
17. We Have So Much in Common!
I was really getting into this girl and finally managed to ask her out on a date. When we get there, things are going smoothly. Then I bring up the fact that my grandparents are straight out of Sicily. Then I say they’re from a certain town, and she says her parents are from the same town. She goes home and, surprise surprise, she’s related to me! We never spoke again.
18. Quite a Transformation
I’m a straight male. When the Transformers movie first came out, I didn’t realize that Shia LaBeouf and Megan Fox were different performers. I knew there was a “hot girl” in it, and I also knew that a person named Shia LaBeouf was in it, who I thought was female. Every time someone talked about the Transformers movie for a 6 month period, I always commented on how hot Shia LaBeouf was.
I always got weird looks and never knew why. Finally, I saw some trailer or something that made me realize my mistake. Not one of my friends could have corrected me!?!
19. See You Never
My husband and I were going to Thanksgiving dinner at the house of some of my dad’s family that I only kind of knew. We got there, knocked, and a woman I didn’t recognize let us in. We went into the home and there wasn’t anyone there. There was also no dinner or sign of any event hosting preparations. So we’re making small talk with this lady and I ask when everyone is coming.
She asks what I mean. Turns out we were at the wrong house. The woman just thought we were friends of her husband’s because he would often randomly bring people home, and that we had simply arrived before he did. We left and never mentioned to anyone at the real party that we had been in another house on the way there.
20. An Act of Dominance
I’m a big guy, but my fiancé’s dog always acted dominant around me, and tried to hump my leg on several occasions. So, one day on the back deck of our house, she went at me again. I decided to show her who’s boss. I grabbed her from behind and started humping her. I did this for, I don’t know, 10 seconds. You might guess where this is going…
When I looked up, the new neighbors—who’d just bought the house next door, were all standing in the yard holding their cardboard boxes… just watching me. At the moment, I thought, “It will seem odd if I stop now.” So, I kept going and just waved to them casually. They didn’t say a word and the next week, I kid you not, they put the house back up for sale.
21. Caught With Your Pants Down
In physical education at school, we had to do this thing where you lie on your back with your legs in the air. You then move your legs in a pedalling motion. I was chosen for a demonstration. This turned into an utter disaster. I was wearing boxer shorts, and imagine how embarrassed 12-year-old me felt when some of my junk popped out to say hello.
As discretely as I could, with about 30 people watching, I tucked it away. When it was mentioned afterwards, I just denied that it had happened. Denied it repeatedly in the hope that everybody present might just decide they were mistaken about what they believed they saw. I don’t think it worked in the slightest.
22. Double Trouble
I went out to eat with my family once. After we were seated, I glanced at the table next to me and noticed some girl staring at me. I thought it was weird, but continued chatting with my family. I looked over again and she was still staring! After checking a third time, I noticed she was giving me a nasty mug.
I finally stood up to say something, and quickly realized it was a mirror…I was about to have an argument with my reflection.
23. Sneak Attack
Back in high school, I was a socially awkward geek. In French class, I answered all the questions right. After my 15th question, the popular girl behind me goes cough, nerd, cough. I cough and cuss at her. The whole class gasped—I had cussed out the popular girl in class. We get then got into this teenage tussle, which was already embarrassing. But it got so much worse.
I turn around to see her and suddenly… I get the huge urge to sneeze. I sneezed all over her. My snot was like a web between my nose and her face. I was sent out of the classroom, as the girl screamed and started crying. An hour later, everybody knew what I’d done. I don’t know if I ever lived it down until I graduated and left school.
24. A Proper Send-Off
I accidentally tooted very loudly at my grandmother’s funeral in the middle of her sister’s eulogy speech. I was 17. Everyone heard it.
25. A Blissful Flight
I will never forget this… ever. I was on a long flight a couple of years ago. I ended up falling asleep for something like six hours. Upon waking up, I decided to just keep lying down with my eyes closed and relaxing. However, due to my extremely dreamy state, I believed I had just woken up alone, in my room as usual. And what do I do when I wake up alone? I pass gas. A lot.
I started to just let them rip, one after the other. And not quiet ones… these were loud and smelly. After a few minutes of nonstop action, I open my eyes. The old lady next to me is freaking staring at me, along with half of the other passengers on the plane. The whole place smells foul. I was so ridiculously embarrassed that I just closed my eyes and pretended to sleep for the rest of the flight.
26. Going Down?
I was working on a project at work one day and ended up staying really late. I ordered some Indian food and whatnot so I could get out as soon as possible. Normally my building clears out around 5:30-6:00 pm, and I was there till about 10 pm on this one particular evening. On my way out, I jumped into the 14th-floor elevator and it started to descend.
Thinking I was the only one who could possibly be in this building at this time, and I ripped a big nasty Indian food toot. I realized my mistake too late. Just as I finished, the elevator stopped and three models from the modeling agency on the 13th floor got in. Just the most beautiful women you could possible imagine, getting in at the exact wrong time.
I started to panic since the smell had not risen to nose level yet. As the door shuts and we start to descend, I’m staring down at my phone and just waiting for the inevitable to happen and put me out of my misery. The girls were giggling and talking about what they were going to do for the weekend and then all of a sudden, silence.
At this point, I was wildly laughing in my head and yet also wanting to curl up and hide all, at the same time. I was staring down at my phone hunching, hoping that they wouldn’t be able to see my face, while we made the trip down the next 12 floors, which seemed like hours. They knew it was me, obviously. That was the longest elevator in the world.
27. Can’t-Miss TV
When I was about six, I was watching an episode of Pokémon. I had to pee but didn’t want to miss anything, so I peed in a trash can. I thought that was super clever at the time but as soon as my mom got home she could smell it. 21 years later she still remembers it and brings it up whenever she sees fit. I’m full of regret.
28. Caught Red-Handed
I once sat on a red pastel crayon in middle school. I was wearing white pants.
29. Midnight Run
I was at a friend’s house for a sleepover, and I woke up in the middle of the night to go to the bathroom. I open the door…and there is his mom shaving her parts “down there” with an electric razor. I stood for what felt like an eternity, but it couldn’t have been more than five or six seconds, simply staring at this and trying to comprehend what was happening.
She said my name really quietly, half as a gasp. Then she flicked the switch off, yet held the flamingo stance over the sink she’d been in when I entered. I said “Uhhhhh” and ran back to my sleeping bag, pulled it over my head, and tried to go to sleep. The next morning, she never left her room and said she was ill. I was never allowed to stay at his place again.
30. Midnight Snack Attack
I got up one night to get some water, and found that my teenage son was in the kitchen getting food. He was behind the kitchen counter, so I could only see him from the waist up. When he came around the counter into the hall, two things happened simultaneously: He noticed me and his eyes grew wide in horror; and I saw that he was butt-naked except for a pair of socks.
He tried to panic-run backward on the tile floor, but ended up slipping and taking a hard seat on the tile. Worst of all, he dropped his Hot Pocket. I made sure he was ok, then went back to bed and laughed my backside off. Years later, we were driving and reminiscing about funny memories. I said, “Do you remember that night when…” and he cut me off with, “Yes.”
31. No Kids Allowed
My place of work has a 21 and over policy after 9 pm, and a group of people walked in. I immediately assumed they walked in with their child because I couldn’t see her over the counter. So I said, “Hey guys, I’m sorry but we’re 21 and over right now.” It turns out she had dwarfism. Oh my lord. I was so incredibly MORTIFIED.
32. Driving the Point Home
In middle school, my crush’s mom and my mom drove the exact same SUV. They even had similar license plates. After school one day, I ran up, hopped in my mom’s car and started talking. When she didn’t talk back and hadn’t left the pickup row after about 30 seconds, I looked at her. What I saw made my blood run cold.
She was not my mom. I look to my right and my crush is standing outside the car looking at me like I’m crazy. I sheepishly got out and ran a few cars back to my real mom.
The first time my girlfriend and I went out on a date, we went mini-golfing. Wanting to be the awesome, cool new boyfriend and assert my dominance, I jumped across a river and made it. But on my attempt to jump back, the rock I was stepping on slipped and I fell sideways into the river. This is the exact moment I found out a very uncomfortable truth.
Mini-golf courses dye their “rivers” blue. My white shorts were dyed blue along with my shirt and half of my body. I ran through the mini-golf course, jumped over the fence to the parking lot, and waited in my car until my girlfriend could stop laughing enough to get in the car.
34. The Seven Seas of Regret
Stuck on a cruise ship for three days after my friend proposed to his girlfriend on the first freaking day and she said no. That same first night she made out with some random guy in the hot tub. I’m honestly not sure how devastated my friend actually was, but it was intensified by the fact that he’d drink himself stupid daily by 2 pm, which would lead to him going to beg her to get back with him.
At one point, she was sitting on the new guy’s lap at the bar and he grabbed her hand and “confessed his love for her” for what must have been the fifth time in two days. It was a constant battle of trying to pull him away and convince him to either go to sleep or come with us to another part of the ship. He is a good friend, so I felt terrible for him, ‘cause that was super awful on her part and tried to help him all he would allow, but it was awful to watch.
By the end of the cruise, the entire boat it seemed like knew what had happened. When I tried to bring it up with my girlfriend (who was on the cruise with me as well) days after we got home, she straight up refused to talk about it, saying that was painful enough at the time so we never need to speak of it.
35. Indecent Exposure
I was wearing a long dress on an escalator at an airport and it got stuck in the stairs. The gears were pulling in my dress and I was fighting like heck to pull it back out. The escalator was eating my dress and my underpants were rapidly being exposed. I am looking around and start seeing people looking at me in horror. But that was just the beginning.
When I finally got the dress out, I hobbled to my gate I realized that the waiting area that witnessed my incident was the seating area for my flight. Everyone I’d be spending the next nine hours with saw it happen.
36. The Original Captain Underpants
When I was a young kid, we had a pajama day at school. Well, I always just wore my boxers to sleep. So guess what? I showed up to school in pretty much nothing but underwear. Why my mom allowed me to go in that way and even drove me there, I have no idea. It was the most embarrassing day of my life, and the school had to call my parents to come pick me up.
37. Press Play
The first time I met my ex-girlfriend’s parents and family, it was Thanksgiving, and the PS2 had just come out. We were having dinner and her whole family was there celebrating. Her dad and I start talking. He says he is a big gamer and would love to try it, so I go and get it from my house along with my VCR because their TV was old and it was the only way the PS2 would work.
So, he starts playing something. Then about an hour into the session, my ex’s little sister is sitting next to the VCR I brought, and accidentally hits play with her foot. This causes the VCR to play a tape. Its contents mortified me. Yep, it was very “adult.” Up pops a girl on screen—right in front of my ex’s grandmother, little children of the family, mom, everyone.
Her dad just says, “God darn satellite!” and tries turning it off with the remote. I wait a second, probably a little too long, and shamefully get up and walk over to the VCR to turn it off. Her dad says, “Wait was that yours?” Embarrassed as heck, I say, “yep.” Everyone laughed and my girlfriend was so angry, but I ended up being with her for three years so it must have not bothered her dad too badly.
38. I Wear the Pants Here
This wasn’t me, but one time my friend, who’s an actor, was on stage for the final performance of a show he was in. His pants were about six sizes too big, and he didn’t have a belt. Well, that last night, his pants fell down. No big problem, he was playing a hobo, so he could have just picked them up and held them… too bad they took his boxers with them. He was naked from the waist down. His parents and his girlfriend were watching.
39. It’s Okay, I’m a Professional
Oh my god. I was beginning to become interested in women and I wrote down a list of jobs that I wanted to have when I was older. I thought the perfect job would be a professional chest massager. That was the top of my list. My parents found it and just didn’t say a word. I’ve not heard them say anything about it ever again.
40. Long in the Tooth
I was standing in line at Wal-Mart, and the guy’s dentures in front of me fell out onto the ground. I didn’t realize what he dropped, so I bent down to get them…and saw it was a full set of teeth. I then decided not to touch them, thinking he wouldn’t want me to because he had to put them back in his mouth. Turns out, that was just the beginning of my nightmare.
Then after standing back up, I felt like that was rude and he might think I didn’t touch them because they are “gross.” So I changed my mind yet again and bent back down to grab them, but as my hand was like three inches away, I thought to myself that he definitely doesn’t want me to touch them, so I stood back up.
The entire time, this guy was standing there watching me bend down and stand up several times. The final time I stood up, he locked eyes, gave me a weird look, then snatched them aggressively and walked away. I still have no idea if I should have grabbed them or not. It was just embarrassing having him watch me be indecisive about his teeth.
41. Kissing Cousins
I accidentally matched with my cousin on Tinder. I was like “Wow, she is hot—wait a second, that’s my cousin!” while rapidly swiping. It was too late. It all happened so fast and I had already swiped “yes” before I realized who she was. Same thing must have happened to her, because we matched. I just messaged her and said “We never speak of this, agreed?”
42. Whipped Cream
I used to wait tables. During a busy lunch rush, I had to make a sundae for a table in the very back corner of the restaurant. I get to the table and the entire party starts laughing. I’m standing there holding the sundae, super confused. I look down and realize that I had somehow managed to get a large amount of whipped cream directly over my crotch while preparing the sundae.
It was nowhere else on me. Just my crotch. All I could do was put the sundae down, say, “Oh my gosh!” and speed walk back through the entire restaurant to clean myself up.
43. The Wedgie
I was at an IHOP with some friends and had received a serious wedgie upon sliding into my booth. The longer I sat there, the worse it got, so by the time we finished eating I was ready to fix the problem. I stepped out the front door and around the sidewall of the little entryway to pick it, and since no one was driving through the parking lot, I figured I was safe. Big. Mistake.
I was digging, hand down the back of my pants, yanking out the offending cloth, when one of my friends walked around the corner and immediately started laughing at me and pointing. It took me a second to figure out she wasn’t laughing at me, but the poor family having breakfast behind the plate glass window that was looking at me in horror.
44. A Nice Dinner Photo
I got my wife an early birthday gift; a smartphone, the first one ever for her. But when her actual birthday rolls around, since I’d already given her her big gift, I decided to give her another kind of treat. I sensualized myself up. Oil all over me, a tie and some shirt cuffs, no other clothing. I was going for a Chippendales dancer look.
I call her back, and she is rolling in this—just loves it. Takes a picture with her new phone. Then the plot thickens. We go fishing later, catch a few, and filet and cook the fish. It truly looks like a gourmet meal. Wife takes a picture of the fish with the phone, but before she goes to bed, she uploads it to show off our nice day together…
Except she accidentally uploads my Chippendales photo, thinking it was the prepared fish filets. The worst was the caption. She titles it, “Dinner Yum!!!” We deleted it on the computer, but not before it got two comments..from her mom and sister.
45. The Family That Eats Together…
I was at my best friend’s house, and in the middle of dinner with his family, his parents decided to announce to their children (and me) that they would be getting a divorce and splitting up the family. The most embarrassing and worst part was that I couldn’t leave, because my parents were out of town and I was staying with them.
46. You’re Screwed
I was born missing one of my cuspid teeth, and I had a tooth implant done just a few years ago. In other words, they put a screw in my mouth. Not long after, my boyfriend’s dad had a surgery where they put a few screws in his hip. Hearing this news, I immediately told him, in front of their whole family, “Hey, we can be screw buddies!!” They still won’t let it go.
47. The Singers
Yesterday, I was about to walk around the corner of my apartment building to go through the alley to the parking lot. No one was around and for some reason, Paula Cole’s “I Don’t Want to Wait” popped into my head. I’m a pretty good singer and I’m good at funny voices, so I belted out, “I DONT WANNA WAIT!!” in this goofy tone as I turned the corner.
The moment I’ve completed my turn of the corner I’m face-to-face with some dude who simultaneously turned the same corner in the opposite direction. Now, I know he heard me. We’re face to face, about eight inches of tense, awkward air separating us as we stare at each other right in the eyes, his dumbfounded bemusement counterbalancing my quickly escalating panic attack.
I didn’t know what to do. He didn’t know what to do. We held this pose for about five seconds and then, never looking away for an instant, I sang in a decrescendo, “For our lives to be over.” I don’t know why I did that, but it had no effect on this guy. So, I just walked around him and shuffled down the alley, already trying to suppress the memory of the awkward moment.
I looked overt shoulder, and saw he hadn’t moved, but was looking at me as well. I still don’t know if this was in my head or not, but I swear as I walked away, I heard the faintest singing voice, “I want to know right now what will it be?” When I looked back, he was gone. I haven’t seen him since. I miss you, stranger.
48. The Black Sheep of the Family
I didn’t know alpacas were animals until I was 27. I thought “alpaca” meant “made from llama hair,” much like wool is “made from sheep hair.”
49. The Truffle Shuffle of Shame
In seventh grade, some girl was wearing a Goonies shirt. I had no idea what it was, but it looked like a punk band or something and she was preppy, so my emo self tried to act offended and said, “Do you even listen to the Goonies?”
50. Tyrannosaurus Roar
A few years back, I was trying to get with this girl. She was way out of my league, but she was a friend’s sister and was pretty into me. So, I invited her, her sister, and a few of her friends over for a party. Things were going great until a dude and his girlfriend wound up passing out in my bed, nixing the fun plans I had for the evening.
I was bummed to say the least, but the girl snuck into my room and stole my comforter and pillows from them and was like, “Let’s just sleep on the floor in the living room.” SCORE! Things were awesome as everyone else filtered into the other bedrooms or went home. We made out all night, but that was about it. We eventually passed out spooning.
The next morning, I heard her leave, and almost immediately after the door shut, I let out one of the single biggest toots I have ever let fly in my 27 years of existence. I’m talking about one of those ones that leaps out of your butt with a tyrannosaurus roar. If you would’ve had a slow-motion camera pointed at my butt you could’ve seen the shockwave. Then I looked around and went white as a ghost.
Little did I know that the object of my affection was still lying next to me and wide awake. She hadn’t left. It was her sister, whose voice was almost identical. My date awkwardly left, and then later that day, her sister called me to ask if I had pooped myself. I was mortified. And, needless to say, things didn’t go too well between us after that morning.
51. An Old One and Not a Good One
This was in high school. She invited me to her house to have dinner with her family and I didn’t know them very well yet. The conversation turned to names we thought were old-fashioned and ugly-sounding. We all threw out a few like Gertrude, Bertha, and Eugene. Then I said the one thing that ruined everything.
I said, “At least that one’s not as bad as Deborah!” I used my ugly voice and everything. Her mom’s name is Deborah. Her grandmother was also at the table with us.
52. Sweet Disaster
We order a small snack for our coffee and as it’s arriving at the table, he pulls out his Nokia phone. Trying to make a lighthearted joke, I say, “MAN, that has got to be the oldest phone I’ve seen in a while.” I really dug it in, trying to break that awkward first date wall. Well, it turns out that it was not a Nokia, it was his insulin pump.
53. Gone for Six
When I was 16, my friends and I were playing baseball. Somehow, the ball hit me directly, directly, in my crotch. The ball cannoned into my love spuds at an incredible rate. The first sensation was an intense stinging feeling, like a hornet had stung me. This quickly gave way to the most intense nausea I have ever experienced.
I projectile vomited everywhere, all the while screaming. While this was going on, I remember my friend saying in a panicked voice, “WHAT HAVE I DONE, he’s never going to be able to have kids!” At some point, one of my friends called an ambulance and it arrived fairly soon after. To add to an already fairly humiliating situation, there was a very pretty 18-year-old girl who was riding around with the ambulance for work experience.
I have a clear memory of her shrivelling up her face as the EMT examined my swollen member. But then it got even worse. I went to the hospital, where, after examining me, a female doctor instructed me to pleasure myself as soon as possible and to inform my parents if there were any difficulties or “unusual discharge.” Mortifying.
54. It’s All Fun and Games Until…
One day, I was taking a long leg cast off of a kid who was about three years old. After I got the cast split open, I started to pull it off, and the Mother suddenly said, “Oh, his toe fell off.” I chuckled and replied, “Nice one,” thinking she was joking. She gave me a really angry look. It turned out that the kid had been in the cast because his small toe had been nearly amputated and then reattached.
The doctor was hoping that what tissue was still connected would be enough to vascularize the distal portion. It wasn’t. The kid’s toe had rotted and fallen off. Whoops.
55. 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. 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.
56. Circular Logic
I was at my office, maybe a week or so into a cool new job. I shared the space with two of the bosses, but I was alone because everyone had left for lunch. So, I started spinning around in my chair just for the heck of it. Like, spinning HARD. Then, I suddenly hear a tap on the window and it’s my boss who had forgotten his wallet. I couldn’t look at him for the rest of the day.
57. Getting Nosy
I was waiting for an online interview to begin for an internship program that I had applied for. While the interviewer was away, I suddenly remembered that I still had my septum piercing on. Naturally, thinking that it might look unprofessional, I started trying to push it inside my nose before anyone could notice.
As I was adjusting the now hidden piercing, the interviewer came back online and saw me basically appearing to pick my nose like an idiot. We had an awful five seconds of silence before she decided to proceed with the interview as if nothing had happened. I got the internship and now have to avoid her around the company because she always seems to remember and look at me funny.
58. Dragged Along
I was 13, and my family and I were on a skiing holiday. My parents had decided to sign me up for lessons, so that my dad could get some good skiing in and my mum and sister could relax and drink hot chocolate. I had been throwing myself down mountain slopes with about as much grace as a brick, and I was exhausted.
We had time for one more run, so we all waddled over to the T-bar machine. Somehow, my jacket got caught on the bar, which knocked me to the ground. Somehow, it got more embarrassing. It then dragged me along the snow toward some rough ice that managed to pull down my ski pants, thermals and underwear, exposing my bare bum to an entire slope of people.
When I finally got help, I cried the entire way down. The real kicker was getting back, telling my family this story while still sobbing through wounded butt and wounded pride, and having my dad and sister howl with laughter while my m0m desperately tried to comfort me. I still don’t think I’m over it to this day.
59. Open-Door Policy
I once had a terribly annoying itch around my private area, so I pulled down my underwear to give it a scratch. Unfortunately, I forgot that my bedroom door was open…and that my parents were entertaining family friends in the living room. I was 13 years old at the time. I wanted to literally end myself right then and there when I realized what I had just done.
60. Beware the Two-Way Mirror
I was once in a meeting in my client’s boardroom. The boardroom was at ground level and the exterior glass was mirrored on the outside, but see-through from the inside. In the middle of the meeting, some sketchy looking dude comes over on the other side of the glass and starts picking his teeth in the mirror.
He looks left, looks right, sees that he has privacy. Then his actions scar us for life. He decides to whip out his private stuff to start intensely inspecting them in the mirror. My client just got up, walked directly over to the glass, and gave a little rap on the window in front of him. He immediately pulled his pants up and walked away.
61. Jerry, Jerry!
I was hanging out with a friend, out walking, and we ran into someone he knew from a while ago. They chatted for a minute, and then my friend asked, “How’s Jerry doing?” Without missing a beat, his friend replied, completely deadpan, “Oh he’s dead.” I burst out laughing, and the guy looked at me as if I was the most inappropriate person in the world. He was not joking. Jerry was gone.
62. Chalk It up to Youth
So, when I was really little, maybe around five, I used to take pieces of chalk and stick them in my butt crack. After a while, the chalk would start to sting, and for some reason, I liked it. One day, I lodged a good three pieces in between my cheeks and went about my daily activities. At some point while playing, I broke a vase.
Since my dad wasn’t home, my mom decided to give me a little spanking. She pulled down my pants, bent me over her knee, gave me a tender wallop on the rear. I braced for the second impact, but it never came. I looked around to see my mom staring at the ground, where two of my butt chalks had landed. Her jaw was on the floor.
Eventually, I got up and ran to my room, as my mom continued to sit motionless for a number of minutes. I never head anything about it after that, but I stopped the strange practice.
63. Funny You Should Say That…
One of my animal shelter buddies messaged me some text and two pictures over Facebook. I didn’t scroll up to the text; I only saw the one pic, which was a very funny looking dog. It was a fat Chihuahua that had a very bewildered look on its face. I replied “LMFAO” and then forgot about it. A couple of hours later, I looked again. I actually scrolled up that time and saw the text. That’s when my horrific mistake dawned on me.
It provided backstory to the picture of the funny-looking dog. A man had passed and my friend was trying to rehome his two dogs…to which I had replied LMFAO. So, I’m an idiot. I tried to explain and apologize, but I still think she’s a bit salty about that.
64. A Lovely Teacher
A teacher whose name I don’t even know at my son’s daycare said, “Bye, love you too,” after I told my son, “Love you buddy, have a good day,” on my way out. I’m pretty sure she had a morning full of cringe.
65. Chump Change
About a year or so ago, I was standing in line at the grocery store, waiting to pay for my small grouping of items. The man in front of me is elderly, maybe late 80s or early 90s. He has finished his transaction and is trying to get his wallet out of his pants to pay. Now, this guy’s clothes are about two sizes too big for him, so everything is kind of hanging off of him.
Because of his advanced age and loose clothing, reaching into his back pocket to retrieve said wallet is proving to be extremely difficult. He seems to lack the strength and coordination to both maintain his reach and grab the wallet from the very deep and loose back pocket of his old man pants. This goes on for, without exaggeration, five solid minutes.
Picture a grocery store with lots of people trying to get dinner and whatnot, and everyone is basically on hold while this guy tries and tries to get his wallet out, to no avail. Now, here comes the horror. Old man, WITHOUT A WORD TO ME, points his rear end at me and just looks into my eyes. I realize that HE WANTS ME TO GET HIS WALLET OUT FOR HIM.
The realization hits me and I am frozen. There are like 10 people in line behind me all watching this happen, and who want to get home in time for Jeopardy. I start to do nothing, but then realize that this dude is genuinely looking for help. So, I reach into his back pocket to try and retrieve the wallet as quickly as possible. This is when I realize what the real problem was.
The dude has a Costanza wallet x 10. It’s huge. And heavy. I am trying to get a grip on the thing and I cannot get it past the loose fabric of the deep pocket, and more folds of what I realize are HIS OLD MAN FLOPPY BUTT FLESH. I swear I tried for like 30 seconds to get the thing, and couldn’t. But it wasn’t even over.
At this point, I turn around and see the horror on some people’s faces, because to the untrained eye, I am a dude sticking his hand down a poor old man’s pants. In a grocery store. In broad daylight. It’s at this point that I give up and tell the guy “Sir, it’s all good your stuff is on me.” I cram my card into the machine and pay for his stuff, which is only like $12.
He thanks me and shuffles out of the store while I pay for my stuff and slide off to my new life as a predator of the elderly.
66. The Butt of the Joke
My husband and I had an inside joke. Whenever someone lost something, the other person always asked, “Have you checked inside your butt?” I was in a meeting at work in my conservative and traditional corporate office one day, and a co-worker said, “I can’t find my pen.” Without any thought or hesitation I quickly responded, “Have you checked inside your butt?”
67. Slippery When Wet
Oh God…here goes. Working at McDonald’s three years ago, little kid spills coke on the floor. I happily wander over to clean it up. Mop that stuff up lightning fast with a smile and everybody is happy. Go behind the counter and retrieve the “slippery when wet” sign to place over the newly-cleaned area, and when I get there, distracted by something, I slip!
My foot slips out like a javeline and kicks a baby’s high chair, the baby’s head whiplashes against his table so hard both of his shoes fall right off. I just stared in horror at the family. I place the sign down like an idiot and run back behind the kitchen for my dear life. Then I proceeded to crack up in the most maniacal nervous laughter accented with breaths of horror. What had I done?!
68. And Then There’s Darrell
I accidentally mixed up an inside joke with the wrong friend group, with disastrous results. Friend group #1: The “joke” was when someone calls and asks who’s all 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 who I hadn’t hung out with in a while. It was a kind of get together to remember a friend they had who had recently perished in a car accident. I didn’t know him that well, but I was always down to party. Anyway, the phone rings, and the person who answered started listing off names.
Sorting my cards for another round of President, I offhandedly said, “heh and Darrell!” It was the typical record-scratch moment where everyone stopped and looked at me. Except then it got even more awkward. Darrell was the name of the friend who had just passed. This happened in 2002 and I still think about it all the time.
69. Going for a Ride
I was walking into a dorm building with a friend one time, and she saw one of our friends coming into the dorm a few hundred feet behind us. She decided to scare him, so she hid behind a big pillar right near the entrance. The guy walked through the door, and she jumped onto his back, grabbed him around the neck, and started smacking his butt, yelling “Giddyup, Cowboy!”
The guy flipped out and got my friend off of his back. At that moment, her blood ran cold. It was not our friend, it was just some random, strange guy. My friend turned bright red and ran up the stairs without saying a word. From then on, that guy would see her sometimes in the halls and say “Hi, Cowgirl” and she was always way too shy to reply.
70. Loud Laundry
While I was in grad school, I lived in a basement apartment of a pretty big building. Right next door to me was the laundry room. Normally it wasn’t a problem, but this one washer decided it was going to be particularly loud. I was studying for finals and trying to concentrate, so all the noise was just a nightmare and I couldn’t get anything done.
In a moment of exasperation, I ran out into the hallway in my boxers and a t-shirt and into the laundry room. I lunged at the offending machine, shook it violently and screamed at it, “Shut up you darn washer, don’t you know I have finals this week?!” I talked at it like a psychotic person, “I control whether you live or die. Can’t get anything done. Don’t make me hurt you.”
And then I turned around. There was this beautiful woman who lived in my apartment building standing there, staring at me, petrified. She just held her detergent and roll of quarters quietly, eyes bulging. She nodded politely when I stammered about how, “I’m studying for finals… uh, it was being loud.” About a week later I walked by that woman and her friend and I heard her whisper, “Oh my god, it’s that guy. The guy from the laundry room I told you about.”
71. Take a Hike
In terms of real life, a buddy of mine was talking to this girl we all knew, and they’d been getting pretty flirty. So, the decision was made to invite her camping with us in the hopes one of them would make a move. Flash forward to that night and our buddy did seemingly everything he could to screw it up—spilled beer on her, stuck his finger in her mouth for no reason while she had a look of what the heck is going on here.
Finally, somehow, she still didn’t hate him and toward the end of the night, he tried to kiss her and headbutted her pretty darn hard because he moved in too fast. After this, they had a talk because this girl was apparently the crown princess of second chances, and he threw up on her. Obviously, this was God’s way of intervening.
72. Nice Save
One time I went to send my buddy a picture of this girl I matched with on a dating app. Derp no. I accidentally sent it to her instead. Talk about freaking panic mode. Felt like the biggest creepy tool ever. My saving grace was that the picture wasn’t just of her, and had some of her friends in it. She texted, “Why did you send me this?” My mind worked at the speed of light to recover the situation.
I responded with “Who is the girl to your left? She looks super familiar. What’s her name?” even though I had never seen her in my life. My buddy still rips me to this day about it.
73. The Limp
This little event took place about a year ago, and it is by far the most embarrassing moment of my life. I was at university during lunch hours, and I suddenly felt an urge to release the chocolate hostages. This is actually a rare event, as I’m not really comfortable pooping in public, but as the university was almost empty, I figured the situation was at least as good as it could be.
In my search for the most abandoned bathroom on campus, I eventually found the perfect spot. It was clean and big, it even had some fancy armrests on each side. I sat down and enjoyed one of my best poops ever. I sat there pondering, and started reading the newspaper. After about 20-25 minutes, I had to get ready for a lecture and started finishing.
The lecture room was nearby so I wasn’t really in a hurry though. I folded the newspaper neatly and put it my bag, washed my hands, and opened the door. You probably guessed it, but no, not only one person was waiting, TWO people were waiting. And oh my god, it didn’t end there. See, they were in wheelchairs, each of them with their personal handicap assistant.
In a moment of shock and embarrassment, I realized I had chosen the only handicap wheelchair accessible bathroom on the entire campus. The floor was swallowing me. It felt like a blackout. I was traveling through distant galaxies, and then I just froze. I stood still like a model posing for a painter. It was the longest seconds in my life.
Well, this is where it gets uber awkward; some part of me thought, “Hey, we got this bro, relax.” and then I decided to walk with a limp, without saying a thing. The worst part was that when I first started dragging my right foot in the most over-exaggerated manner you can imagine, I knew it was too late to stop, I had to finish my act. I have never been so embarrassed.
74. Trial by Fire
The first time I ever spoke in public was a debate competition when I was 13. Welp, I peed myself in front of teachers, peers, opponents, other schools, judges, and any other descriptor for a person in that 200-person audience. I was embarrassed but decided that nothing more embarrassing would likely happen if I spoke in public again, and now I have no fear of public speaking.
75. Let’s Deconstruct This One…
There was a lot of construction going on in our house and, one fine morning, I forgot to lock the bathroom door before taking a bath. My back was facing towards the wall, but there was a glass vase through which I could see the reflection of the scene that was playing out behind me. One of the workers had accidentally walked into the room.
He froze upon realizing that I was in the middle of a bath. Now, at this point, I had one of two options to choose from: A) pretending I did not see him, or B) shriek like my life depended on it. I decided to go with option A because my mom would have almost certainly fired the poor guy who had accidentally seen her daughter naked. But then it got so much worse.
As I pretended not to know he was there and just continued on with my bath, he literally just stood there for 30 frozen, horrific seconds before running the heck away. If you think that was awkward, well, the truth is that guy had to work on the house for the next week, including my room. He literally couldn’t look at me.
I would constantly have a smile-grimace hybrid on my face whenever I’d see him. On the third last day, when we passed each other in the hallway, he awkwardly gave me finger guns before scampering away like he’d just seen an octopus with the face of James Franco. Yep, the guy just simply never lived that one down.
76. You Had One Job
Back in the dark ages, I worked for a small-town daily newspaper. There was one large discount store that refused to advertise with us, and would only use the other paper in town (our sole rival), which was more of a “weekly shopper”-type paper. For unknown reasons, the store finally decided to give our paper a chance.
Ad ran, and there in the double-truck, full-color ad, was “Men’s shirts $9.99″—minus the ever-important R in “shirts.” Yep. Needless to say, they stuck with the other paper.
77. A Family Affair
When I was 14, I was at a family friend’s Bar Mitzvah and I didn’t know anyone. So, I was sitting there alone and then I saw this cute girl in the corner. I went over to talk to her and then we ended up just walking around this hotel and making out for about an hour. Now, as a 14-year-old boy, that was a big deal to me.
Then she went off to do something. About 15 minutes later, I was sitting alone again when my mom called me over and said, “I didn’t know she would be here, but this is my cousin and this is her daughter.” I look at the girl and realize that my second cousin is the girl I had just made out with. A moment of horror as we look at each other and shake hands. She still hasn’t made eye contact with me since then.
78. Doing the Legwork
So back in high school, there was a girl who sat behind me in Spanish class who loved to put her feet against the back of my chair and push. It was annoying for me, so I would always turn around and slap her legs so she could know to drop her feet. She would do it so much that I got into the habit of just slapping her legs without even turning.
So one day, I feel her feet on the back of my chair as usual and throw back a slap without looking. Her legs felt oddly soft, but I thought I was just imagining things. Her feet remain up against my chair, so I throw an even harder slap. It’s still soft. I turn around to see what’s going on. I had slapped my Spanish teacher’s butt. Twice. She stared at me in shock, said nothing, and then just proceeded to act like it never happened.
79. What’s in Your Toy Box?
I once purchased some embarrassing “toys” online and had them delivered to my home address. I came home one day to find the parcel containing these items open sitting on my bed. With them was a note. Its contents made my heart sink. It was a message from my mother saying “Sorry, I thought this was my parcel!”
I still cringe whenever I think about it. I tried to deflect the whole thing by texting her to ask if she had any wrapping paper I could use for “the joke present I bought for my friend’s 21st birthday party.” Eurghhhh…
80. No Joking Matter
This one has haunted me for years. It was the first week of tenth grade, and I was new at my high school. My other new kid friends and I sat down at a table in the cafeteria, and another new girl sat down with us. She was in a wheelchair. So, I expected her to be really timid and introverted, but she was actually sarcastic and funny, introducing herself and making jokes about being in a wheelchair.
Her: “I’m trying out for field hockey!” Me: “Wait, really?” Her: “Hahaha no you idiot, I’m in a wheelchair.” Eventually one of my friends boldly asks her about how she ended up in a wheelchair. She says it was cancer. My friend asks which kind. She responds, “Leukemia, have you heard of it?” Now, bear in mind, she was funny. She really was.
And come on, who hasn’t heard of leukemia? So, my gut reaction to her response was that it must be a joke. I mean, everyone’s heard of leukemia! It was too late. I burst out laughing. I immediately realized what had happened and tried to cover it up by gasping. It only made it worse. Everyone at the table glared at me. I spent the rest of lunch in absolute silence, and I never spoke to her again.
81. Single and Not Ready to Mingle
I had a tendency to get super obsessive over my crushes growing up. Total lovesick “I will straight-up marry you right now” obsessive. I went the whole nine yards: extravagant love letters, angsty writing in my journal, weird photos and music video montages, dreaming and daydreaming…yeah, all the cringey, creepy stuff.
I was a lonely kid with a lot of feelings and an emotionally painful home life. I didn’t stop until one girl legitimately thought of me as her “stalker” in a quasi-endearing way. That’s when it hit home for me that my idea of love was wrong, and you have to get to know someone to have a relationship with them. Haven’t looked back since, but it’s cringey to think of.
82. Jimi Rocks
When I was 14, my parents went out for the night and left me at home. I was really into Jimi Hendrix at the time, so I decided to order a cheese pizza and listen to my tunes while I waited for the delivery guy. Before I knew it, I found myself with my Guitar Hero guitar around my neck and a tie-dyed bandana on my forehead like Jimi at Woodstock.
At some point after the solo in that song, I managed to open my eyes and I had the life scared out of me. There was some really tall guy with long metalhead hair and a giant beer gut in my bedroom, rocking out with his eyes closed. I actually screamed like a girl when I saw him. I then noticed the pizza box that he had set down on top of my dresser and managed to stop screaming.
He said that he kept ringing the doorbell but I never came down to open the door, so he let himself in. We both laughed about it and I paid for my pizza before walking downstairs with the guy. Before he walked out the door he said “Jimi freaking rocks, doesn’t he?” I could only say, “Yeah, Jimi rocks.” It was a good pizza, too.
83. Heavy Flow
I was in sixth grade with a super heavy irregular period. One day, I was sitting in the front of the classroom, just doing my thing, when a friend of mine came up and whispered to me that I had bled through. That was putting it lightly. My entire bum was drenched in blood. It looked like my nether-regions had slain something and was vomiting up the remains.
I tied my sweater around my waist, walked to the nurse’s office, got a non-blood-soaked pair of pants. And then I had to walk back to a class, in a pair of pants that were not my own, and clean the puddle of blood off of my chair. All in front of a classroom of my sixth-grade peers, most of whom probably didn’t know what a period was. Thank god I moved less than a year later.
84. Career Ender
When I was 13, a doctor wrote me an adult dose for a certain medicine based on my weight. I was a fat kid, but it was the wrong dose and the medicine ended up constipating me…for a month. I did not poop for a whole month. I got sick. I had raccoon-like eyes, my stomach would jump or flutter by itself, I had cramps, etc. It was bad. I was miserable.
I finally told my parents how long it had been since I had gone number two and they freaked out and took me to the hospital. There, they gave me three enemas back to back. After the third one, the water softened all that hard poop just enough that I could expel it. I ran to the nearest bathroom, gown open in the back, and tried to make it to the toilet. I didn’t.
My butt was hovering at a 45-degree angle above the toilet when the geyser burst. This next part is not a lie, but I know some of you will think it is. I got poo everywhere. On the ceiling (somehow), on the floor, the toilet was covered, the walls, even the sink got hit with some spray. Poo was literally, yes literally, sprayed on all walls and the ceiling. It was everywhere.
I felt like a new kid after that. Cleaned myself up the best I could, and then had to figure out what to do. There was no way I could clean it all up, I needed a janitor. So, I walked out and politely told a nurse the bathroom needed a clean-up badly. A janitor was only a few rooms down for some reason, so I saw him go by to clean it, but he did not know who I was.
He got to the bathroom and the whole ER heard, “Oh heck no, I am not cleaning this up. I quit” and he did. I felt so bad, still do. I made some poor janitor quit his job over a poop-caked bathroom.
85. Fair-Weather Friends
When I was in elementary school, the popular girl in my class was having a birthday party. Somehow, I got invited. My parents dropped me off at her house and they were all playing with Barbies. I didn’t know we were supposed to bring them. So, feeling awkward, I went to the bathroom and hung out there for a bit.
When I came out, all the other girls were gone. Like, the house was almost completely empty and quiet. Then the mom came around the corner and asked why I didn’t go to the movies with the rest of the girls…The mom had to call my parents and explain that I got ditched and they needed to come pick me up. That one hurt.
86. Write What You Know
When I was 13, I wrote a pretty detailed fan fiction about my favorite anime. That wouldn’t be so embarrassing, except for the fact that the details included me and a character who was 26 playing strip poker, among other dirty things my 13-year-old mind came up with. But here’s where I really screwed myself over.
I THEN decided to print the story out so I could read it later and make edits. However, I decided to bring it into the bathroom to read while I took a bath, and left it in there when I was done. My dad found it and read it, and let’s just say he was not happy with the writing content his daughter decided to pick.
87. Teacher’s Pet
I always used to volunteer to help out with first-day registration at my middle school. All my friends gave me heck for being a suck-up. But, well, the real reason I did it was if you volunteered, you got to pick your locker rather than having one randomly assigned. And see, I had a gigantic crush on my English teacher.
So both 7th and 8th grade years of middle school, I wound up with a locker directly across from his classroom so I could see him every day. And I found the most ridiculous excuses possible to have to go to my locker. I may have also sent him the world’s most cringe-inducing anonymous valentine my 8th-grade year.
I’m pretty sure he knew it was me, but I didn’t care, I was completely smitten. So it was kind of like that episode of The Simpsons where Lisa gets a crush on Mr. Bergstrom. Except it wasn’t charming in any way. It was awkward and terrible and a wee bit stalkerish. Not having the chance to apologize to him for being such a weirdo is among my biggest regrets in life—unfortunately he passed unexpectedly just after I started high school.
88. Establishing Authority
When I used to deliver the paper in the mornings there was a dog who would always growl at me and it scared me every single morning. I then came to the conclusion that I needed to establish authority. So, one morning I saw the dog and as soon as it started growling, I snapped my fingers and said something like, “You better shut the heck up before I smack you with this newspaper.”
I hadn’t seen the owner sitting on the porch sipping her coffee. She looked at me shocked, I had always been a sweet 13-year-old boy when I went over to do my collections every week.
89. The Audition
I was a big theater geek in high school. So when my mother found an audition for a Renaissance fair, she insisted that I audition. Flash forward…she tells me auditions are in costume so she bought me a really cheap, bad costume from a random website. The audition was at a really waspy country club. So, I show up in my awful costume. I immediately turn red.
I enter the country club and I have no idea where the audition is. There’s a ton of people in there and they are staring at me and laughing like I’m a joke. I am literally almost in tears. Finally, I ask a server because I have no freaking idea where the auditions are. He gives me directions that make no sense, so I wander this place for what feels like forever until I find the room.
I enter, and the panel looks at me, repressing their laughter. I want to end myself at this point. They say I am “definitely looking the part.” I do not get the part.
90. The Affair
When I was 14 and almost always thought with my junk, I decided it would be great to pleasure myself with protection on. I liked how it felt and did it all the time for about a week. They also happened to be my dad’s condoms, so, long story short—my mom realizes that so many are missing and thinks my father is having an affair.
She comes crying to me about it and my initial reaction is to deny any speculation that I used them. After realizing that this may end my parent’s marriage, I ran upstairs and with tears coming from my eyes I explained to my mom that I used them, not for intercourse, but for self-pleasure. I cried for an hour.
91. The Men’s Bush
I studied abroad in Germany. Now a nice thing about Germany is that you can drink outside, and nobody cares. So, when I first arrived all fresh-faced and stupid, and my German friends invited me to go drinking at a festival on the river, well, I went. So, as things often go, when you’ve been drinking for a while, you need to pee. And I am no exception to the rule.
Yet somehow, and this is really beyond me, there was no provision for this basic human need at this big festival. So I decided I’d just go in a bush or something. Granted, I was wearing pretty tight jeans, and when you’re a girl, that means that peeing outside is sort of challenging, but hey, I had to go. So, I go behind my bush, ducking from the well-lit street fair to the pitch blackness of the park.
I perform what is just a spectacular acrobatic maneuver, pants around ankles, bracing myself on two different trees to avoid peeing on my pants. I heave this big enormous sigh of satisfaction as I begin struggling my way back into said pants. My night vision slowly creeps back and I see a terrible sight. I am not alone. There are at least twenty people peeing here and what is worse, this seems to be the men’s bush. Exclusively. Twenty men, dongs in hand, just a-staring.
92. Wanna Know How I Got These Scars?
I used to wear glasses, hearing aids, braces, and had severe cystic acne. My doctor put me on Accutane (for the acne) and it made my face insanely dry. One day a few weeks after starting the medication, my friend made me laugh hard in class—it cracked the skin on my cheeks and my face bled in the shape of my smile like Heath Ledger’s joker scar. I was an abomination.
93. Eye on the “Prize”
I was on vacation somewhere in Spain. I was religiously working out back then, so I even got a contract for this local gym for this one month. While there, I met this local girl who only spoke Spanish. First we only did small talk, then we went on some dates. First going to the pool with her brothers, later going out alone.
I really liked her, but I didn’t dare to talk much, since my Spanish was…poor. I figured we were just friends. We were out on a date, playing pool, when suddenly she puts some egg-shaped plastic container into my hand. It looks like one of those containers that contain small prizes you get from those carnival machines.
So we were there playing pool, and she pushes this plastic egg container into my hand. I smile and say something like “muchas gracias” and pocket the egg, preparing for my next shot. She shakes her head in protest. She gestures at my pocket. She also says something—well, a lot—in Spanish. Mostly, I understand “No.” I’m lost. When I figured out what she meant, I felt my ears go red.
Finally, she loses her patience, face palms, and shoves her hand down my pocket, where I put the egg. Pulls it out. Opens it. It contains a condom. I finally understand. I’m such an idiot.
94. A Different Kettle of Fish
Years ago, I bought a friend an electric kettle as a gift. Her boyfriend came home one night to find her running out the front door of their apartment with the flaming kettle, and she threw it into the street. She was screaming about how it was a piece of junk because when she put it on the stove, over a flame, it caught fire and started to melt.
He was laughing uncontrollably when he asked, “What did you think the cord was for?” She was so mortified, they broke up soon after.
95. Just Keep Swimming
I was staying at a nice hotel while traveling for work. They had a great pool. I went in there one morning and I was the only one there. I started messing about, recreating the opening scene of Jaws where the girl realizes that her leg has been bitten off, then lots of splashing like the shark had come back for the second go. Then I tried a bit of synchro, kicking my legs up in various shapes.
Then I did a bit of goalkeeper practice by throwing my goggles and diving to catch them. Then I saw a window overlooking the pool and a family of six people eating breakfast and watching me. I’m a 51-year-old man.
96. Catching the Red-Eye
For as long as I can remember, my father had red eyes after showering. I didn’t even think about it. Then one day as a teenager, a friend slept over and in the morning she saw my dad dressed and ready for work, freshly showered and red-eyed. Timidly, she approached and asked him why his eyes were red. His answer made me look at him completely differently.
He simply said “shampoo.” She then, very carefully and as respectfully as she could muster, asked him why he didn’t close his eyes when he shampooed. He laughed and said “What do you think, I’m an idiot? Closing my eyes in the shower! Sheesh!” My dad did a lot of things that embarrassed me…But that one was prettttty high up there.
97. An Act of God
Growing up in a very religious household, we would participate in nearly everything the church offered or planned. Every year, we would go to a training thing in Little Rock, Arkansas, where we would stay at a VERY nice hotel for three days while competing in various events like chorus, puppets, bible quiz, etc.
The last year I participated was my senior year of high school, and I was 18 years old. March madness has just begun and my family went to a sports bar for dinner to watch the first round of playoffs. When we got back, my parents and sister went to the ballroom for a worship service while me and my brother stayed in the room.
He was sitting on the sectional couch with his head toward the extended end, playing on his phone. I was rolling around the room in the office chair that was in there, also playing on my phone. I felt the urge to toot, so naturally I roll to where my brother is laying down and kick my legs up so as to go directly into his face.
In the process of kicking my legs up, I accidentally let it go. I think to myself, “Darn it. Maybe I have another one ready.” Now I’m sitting in the chair while my butt is hanging off the end, holding my legs in the air, butt aimed at my brother’s face. I pushed and a nice loud slap comes out. “Nice” I think as I put my legs down.
As soon as my feet hit the floor, I feel a distinctly warm, wet feeling in my lower region. I jump up while exclaiming “Ipoopedmypants!” My brother looks up at me running to the bathroom and asks what the heck I just said. “I JUST POOPED MY PANTS” I yell while sitting on the toilet and let the rest go. I hear him hit the ground and screech with laughter.
Now, as anyone who has pooped their pants before can tell you, you have to inspect the damage. So I kick off my shorts and boxers and hold them up to check it out, while my brother calls my mom to help us out of this situation. However, he’s laughing so hard that through the phone it sounds like he’s crying and all my mom can understand is “help” through what she assumes is tears.
She naturally immediately sends my dad up to the room. Meanwhile, I’m in the bathroom trying to figure out if I’m holding my underwear inside out, because there’s poop on both the inside and the out. “Ok those are done,” I think, and I throw them away and move to the shorts. But it was the same thing there; they’re done for.
My dad has now entered the room and panickedly asks my brother what’s happening, while he’s still on the ground in tears laughing because I’ve been giving him updates on how bad the poop stains are. Once he gets the story, he calls my mom and tells her to calm down and nobody is hurt, their sons are just idiots. But it got so much worse.
I finally finish in the bathroom and finish up, having my dad bring me undergarments. I go to flush the toilet and…nothing happens. I try again, and the water rises to the top of the bowl, where it stops moving. I let my dad know and he calls the front desk, who sends a maintenance guy to unclog it. The poor sap shows up to fix the toilet with nothing but a plunger.
He walks in the bathroom, comes out 30 seconds later, and says “I’ll be right back.” He comes back a minute later with what looks like a roto rooter to cram my poop down this toilet. He works for about 15 minutes before the pile is gone and my dad gives him a hefty tip before he leaves. I then spend the next 30 minutes attempting to explain what happened to my parents.
98. Biting off More Than He Can Digest
I was dating a 19-year-old guy. I explained that eating raw nuts is healthy, so he bought a bag of peanuts. He complained two days later that he was going to stop eating them because they upset his stomach, so I got a free bag of peanuts, yay! He was stunned when he saw me shelling them and eating the nut. Because he was eating them shell and all. For two days. Surprisingly, that relationship did not end well.
99. The Fugitive
While I was visiting my girlfriend’s family’s home one summer during college, I had to use the bathroom. I had been there a couple of days and had to go “el numero dos.” So I went, it was huge, and it clogged the toilet horribly. Now, this was no ordinary bathroom, either: It’s a makeshift bathroom in the basement that’s half finished.
Panicking, I looked around to find a plunger. There wasn’t one. So, I found a sort of barbecue knife thing, and I tried to stab and cut the poop up, didn’t work. It smelled so horrible, you could smell it up to the kitchen. Freaking out at this point, I asked my girlfriend what to do. Her response was somehow more embarrassing.
She was crying laughing at me, and then told me to just go home—a three hour drive—and flee the scene. Thing is, I actually did it. I got my stuff, headed home, and never ever spoke about it again. Her dad apparently had to try and fix it over the course of three full days. I NEVER EVER will go poop at that house EVER again.
100. Gobble, Gobble
When I took a food-safe course, someone asked if they could wash a turkey with dish soap. He failed the course.
101. If the Shirt Fits
I guess we were still in high school, but we were 18. My buddy Ferris and I were just getting into going to the gym. We went with Ferris’s friend Tom. After working out, in the changing room during some small talk I saw Tom putting on a shirt. Tom put the shirt over his head, but didn’t put his arms through the sleeves. Weird.
He managed to pull the shirt over his torso so that it was adequately on before wiggling all about and bending his arms in odd ways to get them into the sleeves. I didn’t take much notice of it the first few times, but after a few months it was apparent he did this every single time. Tom literally didn’t know how to put on a shirt. At least efficiently.
Eventually, we asked Tom why he put his shirt on like that, and he said something along the lines of, “Wait what, don’t I do it the same way you guys do?” I guess he had never really thought about it before then.
102. Get Your Head in the Game
This is one of the cringiest stories from my past. It was probably the most embarrassed I have ever been. Back when I was in high school, I went out with a girl I had a huge crush on. We went to the zoo and then grabbed some food. It was great and I had an amazing time, but we had to split up in order to get our trains that were going in opposite directions.
As we said goodbye, I awkwardly tried to lean in for a kiss while she went in to hug me. I ended up head-butting her in the face and her nose started bleeding. I was so embarrassed that I asked, “Are you okay” and when she said, “I think so,” I just waved goodbye and ran into the train station. I avoided her for weeks after and never went on a date with her again.
103. What Time Is It?
One time I woke up late for school because my alarm didn’t go off. I am incredibly blind without my contacts and just glanced at the clock and was very late. In a furious panic to try somehow make it to the bus I put my contacts in, dunked my hair in water and grabbed my backpack and jacket as I sprinted to the bus stop.
It was the time of year where it’s dark outside well into the morning, so it was still pitch black. No one was at the bus stop, so I figured I missed. I still waited for quite some time in case it showed up. When I realized I was so late it wasn’t coming I walked back to my house, knowing I would have to wake my mom up to take me to school.
Fortunately, when I walked through the front door, she was already up waiting for me! She greeted me with, “WHERE THE HECK HAVE YOU BEEN?!?!” I responded that I was sorry, but late for the bus and needed her to take me to school. She glared at me and told me it was something like four in the morning.
I had somehow misread my alarm clock in my state of panic and tried to explain that I really did think I was late and was really at the bus stop. She just assumed I had snuck out with friends the night before and was just coming home, something I had been doing off and on for a while at that time. So, I was grounded for sneaking out, when in reality I just woke up too early to go to school.
104. Clean and Clear and Out of Control
In the late 90s, I had a co-worker who complained about her computer being slow. I took a look, and the hard drive was full. The largest folder was her recycle bin. She had never, ever emptied it in years of use. I emptied the recycle, cleared the Temp folder, and the PC started working fine. She was happy until…her big Excel tracking sheet was gone. Oh, No!
She did not know where it was on file explorer, so I asked her to show me how she opened it. She goes to the little storage container on her desktop, named…Recycle Bin. It was normally at the top, but now it’s gone. No backup. Oops…She cried to management that I “destroyed her computer.” The manager laughed when I told her the truth.