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These Awkward Reddit Stories Are Equal Parts Brutal And Hilarious

Mathew Burke

Dates that crash and burn. Horrifically awkward parents. “Jokes” that die on arrival. There are few things more painful than an awkward moment—and these stories prove that they can go from brutal to hilarious in an instant.


1. It’s the Little Things That Trip You up

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.”

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2. Bad Math

I offered to pay for the bill on a first date with a gorgeous girl. She insisted to pay half. I didn’t fight it, but I only had a large bill so I did some mental math, pocketed her money and put my bill in. Anyway, long story short, I did the math wrong and ended up stealing 20 bucks from her. She sarcastically said, “thank you,” and I thought she was being sincere. I’m an idiot.

mkramer4

3. One Wild Ride

After a date, I dropped the girl off in the parking lot where her car was parked. We said goodbye to each other and parted ways without a kiss, as it was our first date. As she got out and began walking across the parking lot, I suddenly got the courage to whip my car around, stop it right in front of her, get out, and kiss her.

In my head, it was going to be like something out of a movie. In real life, I pulled up to her, forgot to put the car in park, got out, walked away from the car, watched her look at me in horror and point, turned around, and ran towards my car as it slammed into another parked car. Just a typical day in my life really…

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4. 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. The guy next to me said to the guy on his other side “How about the rack on that blonde chick?” The other guy replied, “That’s my daughter.” The first guy mumbled something and left at a brisk walk.

valiantfreak

5. Parting Gifts

When I was about 7-8 I was extremely afraid of public restrooms and really had to poop at the grocery store. I decided to sit down to relax my stomach until we got home but in doing so, I accidentally pooped. My sister walked into the aisle and asked what I was doing and I said “looking at stuff.” On the ride home, my Dad asked if I farted so I said “Uhhh, yep” and everyone thought it was gross. By the time we got home everyone had figured it out and I was really embarrassed.

YourBestFriendStu

6. Anatomy Academy

I was watching Police Academy when I was about eight. There is a scene at a beach party where there are a few naked breasts on show. My mum walks in to catch me licking the TV screen where the bare breasts were.

mataranka

7. Cheesy Tunes

About a year ago, my parents caught me singing to my microwave while I was waiting for it to warm up a piece of pizza. This all happened at 4 in the morning, when I thought my parents were staying at a friend’s. Oh, I almost forgot that I was naked.

About23Koalas

8. A Lovely Teacher

A teacher whose name I don’t even know at my son’s daycare once 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.

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9. Mousy Girl

I went on the most awkward date of all time. It was with a girl who revealed that her hobby was buying dead little mice, doing taxidermy on them, and then dressing them up in tiny little metal battle armor and swords to stage historical battles…using dead mice…that she bought online. She showed me lots of pictures before the date ended.

ComedyDude

10. What Are You Trying to Tell Me?

One time, I wanted to do something romantic for my girlfriend. So, I decided to sign her up for painting lessons as a surprise present because I knew that she was getting into painting. She took the gift to mean that I thought her painting sucked. She never took the lessons, and I never got my money back either.

ccasella3

11. 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?”

petalplucker

12. This Is Not the End

I broke my back when I was a teenager in an accident that left me paralyzed from the waist down. Shortly after the accident, this girl from my school walked over and decided to ask me: “So are you planning on ending your life some time soon?” Naturally, my response was “What? No. Why would I want to do that?” She responded by saying, “It’s just that if I was in your situation, that’s what I would want to do…” It was so awkward. Her friends looked mortified. 

manualpropulsion

13. Hopefully, This Never Happens to Anyone Again

I was showing my grandmother pictures from my trip to Washington State. We were having a great time as I was going through the pictures I took at Mount Rainier, Olympic National Park, and the Puget Sound ferry. Right in the middle of a great picture, my wife texts me about wanting to try out our new bedroom toy. It was literally just the smiling devil emoji and the words “Want to try out the new bedroom toy?”

I don’t think I’ve ever blushed so red in my entire life.

calypso_cane

14. A Bridge Over Troubled Water

I wanted to surprise my girlfriend by taking her on a romantic date to a bridge overlooking a river. I couldn’t believe how quickly it backfired. When she saw where we were, she informed me that this was the exact spot where her first-ever date with her awful ex had taken place.

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15. Never Die Up

When my sister was an angsty little toddler, doing any shopping with her in public was always a huge pain. If she didn’t get what she wanted, she would start to loudly yell “die, die, DIE!” and people would stare at us like we were some kind of crazy psychopathic family. Phonetically, though, “die” is how you say “give” in Russian, which happens to be our family’s mother tongue. But sadly, most people who live in the United States are not aware of this fact…

cannibaldolphin

16. So Much for the Language of Love

My sister was on a first date with some guy she met online and was nervous, so she had my significant other and I meet up with them. The guy was super braggy about being able to speak German, not knowing that my S.O. was raised there and speaks it fluently. So, my S.O. tries to start a conversation with him in German. The guy apparently only spoke a few words of German and left embarrassed and without any chance of a second date. My S.O. still feels a little guilty about it.

tthrooowwawayyysladk

17. It’s All Fun and Games Until Someone Loses a Toe

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.

shdwrnr

18. No Kids Allowed

My place of work has a 21 and over policy after nine pm, and a group of people walked in and 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.” Turns out she had dwarfism. Oh my lord. I tried to save myself by apologizing and telling them they all looked young despite obviously referring to her earlier. MORTIFIED.

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19. A Hairy Situation

We’d just left the restaurant after a really nice date and I was wondering who’d make the first move. My date, who was very cute, told me my hair looked nice. I figured now was the time to strike so I flirtatiously said, “Bet it would look nicer with your hands in it.” He replied, in a very confused tone, “…You want me to style your hair?” There was not a second date.

CaptPizza

20. The Follies of Youth

I was like six and didn’t understand acne. Being all six years old and innocent, I asked my mom why my older teenaged brother always had pizza on his face…right in front of him. Worst of all, he cried.

Lockshala

21. 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.

Parallax151

22. 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?”

As soon as I said it, I snapped back to reality and realized I was at work. As you can imagine, everyone went silent and stared at me as my face turned bright red.

glitterphobia

23. You, But With a Woman’s Touch

My buddy tried hitting on my sister. “I always thought it would be cool to have a chick that’s a female version of [my name here].” Swing and a miss.

Strichnine

24. You Just Got Served

I work at a busy restaurant, so I end up saying “corner” hundreds of times a night as I go back and forth around corners and doorways in the kitchen. One day, I was running food to a table, set it down gently, and in my sweetest customer service voice I said “Corner” while looking the customer right in the eye instead of “Here is your soup” or something like I usually do.

They looked confused, my brain tried to reset, and so naturally I said, “Thank you” as if that made it better. I ended up just backing away. It was a lost cause.

cherry650

25. From Smartphone to Sickphone?

One day, an elderly patient of mine came by the clinic saying she was sick. I examined her and found mild symptoms of a common cold, nothing too serious. I told her that she had an infection and this type of infection is treated without antibiotics because it’s not a bacterial infection, but a viral infection. She understood that part, but then she asked me: “So…do I have to stop using my smartphone, to prevent my smartphone from getting the virus?”

yosol

26. The Story Behind the Statement

My son was about three and a half years old. He had been having diarrhea for a couple of days, and all of the constant wiping had made his butt chapped and sore. He was crying often because it hurt so badly, so I figured I’d just put some diaper rash cream on it. He had to go to the bathroom again while we were at the grocery store.

I let him finish up, gave him an extra wipe to make sure it was clean, and then put some more of the cream on it. We exit the bathroom and go over to stand with my wife at the checkout counter. My son then very proudly announces to the cashier, “My daddy just put his finger in my butt in the bathroom! It feels all better now!” I pay quickly and run for my life before any government agencies decide to show up with some questions for me…

sedativecure

27. What a Sight

My Grandmother caught me standing on the sink bent over in front of the mirror looking over my shoulder all because I wanted to see what one of my toots looked like.

HAHno

28. Busted

When the pastor got to the part “or forever hold your peace,” the bride said, “Yes, I’d like to say something.” Then she turned around to her guests and said, “I’d like to thank my maid of honor for sleeping with my fiancé last night.” With that, she threw her bouquet down and stormed off. The story even made it onto local radio at the time.

PTSDPillowGuy

29. Special Delivery

A girl who was enamored with my neighbor showed up at his house on her birthday to give him a present. So he, not wanting to see her, sent his mother to the door to make her go away. My neighbor’s mom didn’t have the heart to be rude, so she politely accepted the gift. When he later unwrapped it, in front of his mother, it turned out to be a pair of her panties.

We were 16 years old at the time, and the girl in question was 13.

darko

30. Long Time No See

My ex had moved back into our small town after breaking up with her new boyfriend (my ex-roommate). I never avoided her, but I was lucky enough to not lay eyes on her for over a year when I heard she was moving again. That day, as she was walking to her car for the last time to pull out of town, we locked eyes as I came out of a coffee shop.

Holding her gaze, I take one step towards her, inexplicably failing to notice the signboard on the sidewalk, right in front of me. Coffee flies. I fly. From my newly acquired position of moral authority—half on the sidewalk, half in the gutter—I firmly, calmly, say, “Hello. Heard you were in town.” She replies, “You’re lying in dog poo” and rides off into the sunset.

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31. A Meal Worth Marrying

I picked up a pizza, was super excited to eat it, so I put it in the passenger seat and said something along the lines of “I’m gonna take you home and eff you up!” hyping myself and the pizza up of course. I then saw that my window, and the window of the next car was open. A woman watched and heard me talk dirty…to a pizza.

combustablegoeduck

32. He Didn’t Go Bananas for This Research Topic

In high school English class, we went to the computer lab to do a poetry project. Can’t remember the specifics, but I remember we had to find a bunch of different poems that we liked. I had a flashback to my sister reading me a poem about a guy who accidentally hooks up with a chimpanzee, so I fired up a Google search for “Poems about making love to chimpanzees”.

My English teacher’s teacher senses must have been tingling, because he appeared right behind me, and very loudly asked why I was looking for poems about making love to chimpanzees.

TypicalCricket

33. Her Own Secret Admirer

My cousin’s friend came over to stay for a few weeks. She was very vain and before she left, she wrote the creepiest note to my uncle (who is friendly to everyone) saying how she had to sadly reject him, even though she knows how much he is secretly in love with her. We all found the note together after she left addressed to him (he was with us and opened in front of us).

Plainbench

34. Oh Come All Ye Embarrassed

My youngest sibling is more than ten years my junior, so I grew up with him embarrassing me in public on a pretty frequent basis. The worst time I can recall was around Christmas one year, when we went to shop at Walmart after attending a holiday church service. The service was all about the story of the virgin birth, and how no other virgin had ever had a baby before.

My brother was only about four or five years old at the time. While he definitely didn’t know what the word virgin really meant or exactly what made a person one, he had inferred from the service that virgins were people who couldn’t have babies. Anyway, we get to the checkout line after we finish shopping and behind us is a woman who is very obviously pregnant. My brother points to her and screams out as loud as he possibly can, “Look mommy, that lady isn’t a virgin!”

nuggetblaster69

35. The Language of Puppy Love

As a pet sitter, sometimes you get lonely when the majority of your interactions are with animals. So, to combat this I sometimes pretend to be the inner voice of whatever dog I’m walking, responding out loud to whatever they’re sniffing or whatever grabs their attention. Each dog has his/her own individual weird voice as well.

More than once, people have walked around a corner to hear me doing this.

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36. 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 something much more embarrassing. It was his insulin pump.

bacon_butter

37. Too Young to Drive Like That

Oh man. So, I must have been about 12. I was in the car with my mom. To set the scene, it was a three-row soccer mom van, and I was in the second row behind the passenger seat with my mom driving. Well since I was 12, I got my random hormone boner. Strange and awkward enough right? Well, I decided that I would pretend I was driving and that my boner was the stick shift…mom caught me.

Uncanny_badluck

38. An Awkward Coincidence

On my first date with my wife, we started talking about tattoos. I have a rule that if I have an idea for a tattoo, I sit on it for a while to see if it’s something I truly want. I mentioned this to her and explained how glad I am that I do this because otherwise I’d be covered in Tool (the band) tattoos or some, “other dumb stuff.”

Little did I know, I’d just messed up big-time. She rolled up her sleeve to show me that she had the lyrics to one of their songs tattooed across her arm. Oops!

thevagrant88

39. Head Over Heels in Shame

I hopped out the shower one day and was inexplicably overcome with the desire to see if I could balance upside down on my head. I used to do it all the time growing up. Guess I wanted to know if I still had it. The thing is, this desire had to be sated immediately. Even before I threw on some clothes. So, I drop my towel, flip on top of my head and start balancing like the good old days.

Even held my arms out by my side to try it hands-free. Out of nowhere my mother and ex-girlfriend burst into my room without knocking and get a face full of me upside down, naked, in what can only be described as a reverse T-stance. They screamed, I laughed, and I think I clipped through the ground a bit due to the collision.

suisauce

40. First Time is the Worst Time

In high school, I was on the verge of losing my virginity to my girlfriend of two years who also happened to be my neighbor. The scene was set perfectly, both my parents were gone (dad was out of town and mom was working until nine) and I had just asked her to prom that day… So things are getting hot and heavy, and all the sudden I hear a noise downstairs, but assume it’s one of my cats wreaking havoc as usual.

Things continue and about a minute later my (extremely conservative) mom walks in, and as the door opens she lets out a faint scream and runs downstairs. BUSTED. Now while this moment was awful enough, after going downstairs to face my mother who had immediately called my (also very conservative) dad, she goes on a rant about how irresponsible I am and how protection doesn’t always work, and I’m proof of that.

So that’s the story of how my relationship was ruined (just got really awkward after that) and I found out I was an accident.

bluezfawkx

41. It’s-a-Me, Dustin

I went on a date with a guy who faked an Italian accent the entire time. He was from Florida.

BirdBerella

42. A Bill Is Just a Number, Right?

Have this uncle who is extremely cheap and once took us out to dinner. After he got the bill, he asks for the menu again and takes out his calculator and starts double checking the bill prices and menu prices. This goes on for 15 minutes while the waiter patiently waits next to the table. At the end, he realizes he forgot his wallet and asks us to pay. Don’t think I’ve ever tipped that generously.

LifeGuru13

43. Moving Too Fast

I went on a date with a guy named Dan when I was in my late teens. Dan said, “I’d like you to meet my father, he’s going to love you.” So I got in the car and as we started heading out of town, I asked where we were going. Dan said, “you’ll see, we’re almost there.” 15 minutes later, we pull in to a cemetery, and he says come with me.

I was nervous as I followed him down a little hill and he kneeled down in front of a tombstone. He said, “Dad, meet shortcakie, she’s going to be my wife someday.” That was the first and last date Dan and I ever had.

shortcakie

44. An Inconvenient Throwback

Boyfriend finally convinces me to have a threesome after months of begging. I finally agree, and our mutual friend comes over. Things get hot and heavy, and when he starts being with her, he moans “Man, you feel even better than usual!” Everyone freezes. He tries to tell me that he was thinking about me while being with her, and that it just felt differently, but she felt so guilty that she confessed on the spot and begged me to forgive her. We don’t really talk anymore, but last I heard she had been dating my ex for over a year.

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45. Nailed It

I still have nightmares about this date. When I was about 20 or so, I got a date with a girl who I really liked, she was exactly my type and I couldn’t believe my luck. We met in a local pub for a few drinks and things were great. I was getting all the good signs with lots of hand touching and the like. An hour of pure bliss went by and I needed to pee.

After washing my hands, I went to the hand dryer only to find that it didn’t work. I wanted to dry my hands because I wanted more of the hand-holdy stuff. Then I had the single stupidest idea of my life. I thought, “I can fix this!” and put my hand inside the nozzle of the dryer. WHY!? WHY!? Obviously, I got buzzed by the electric heating element, fell back, and cracked my head on the wall.

I didn’t get knocked out but I needed a few minutes to sort myself out before going back. I didn’t have the guts to tell her what had happened; dumb idea number two. I had a banging headache and I wasn’t quite right. Not much later she made her excuses and left and turned me down when I asked her for a second date. A year or so later I found out she had told her friend that she really liked me, but I went to the toilet and came out acting really weird and she “wasn’t up for dating someone on drugs.”

Theory3k

46. Tyrannosaurus Toddler

My three-year-old daughter, who is normally super sweet and very empathetic, was being a total turd in Target this one time. As we were running around trying to get out of the store, she sees someone with an obvious birth defect stocking the makeup shelves. Before we could whisk her away, she shouts out “Look at that guy’s tiny arms, mommy! They’re like TINY T-REX ARMS!” She was so excited for this guy, but he was very clearly not at all amused by her. I was laughing hysterically afterwards, but she was so embarrassed when she realized what she had done that she actually started to cry for a bit.

crashley_earl

47. A Sick Thing to Do

When sitting my dad and stepmom down to tell them that I had been diagnosed with cancer, my stepmom’s immediate reaction was “Are you sure? You’re always overly dramatic like your mother. She watched too many soap operas!” Yes, for real. That is really what she said. Needless to say, it was the most insensitive question I had ever been asked. But it got so much worse.

As if that wasn’t bad enough already, she then decided to start telling people that I didn’t have cancer and that I had faked it. This continued throughout the many difficult months where I was undergoing treatment and a major surgery. Note that she and my dad were both there for this major surgery and all the treatments, so they clearly knew that I wasn’t faking it.

From that point on, at every family gathering, I was constantly asked, “Did you really fake cancer?” Seriously, what the heck?? Anyway, the good news is that I ultimately won my battle with cancer and I now choose to keep very limited contact with this woman due to her toxic nature. The only reason I maintain even my minimal level of contact is for the sake of my siblings.

I have since confronted both my stepmom and my dad on the way they acted during that horrible period of my life, but they just act as if they don’t remember any of it and don’t know what I’m talking about. I’ve shown my medical records to my other family members to prove to them that I was telling the truth. They were all shocked. At least my biological mother supported me…

just-another-cat

48. If These Walls Could Talk…

I got my first kiss on the lips when I was about eight years old. That night, I went home and decided since things were heating up in my newfound relationship, that I ought to get to practicing. I decide the wall is a safe bet and begin to make out with it. Then I start whispering to the wall, pretending it is my third-grade boyfriend. I hear a floorboard creak and look over to see my grandma standing in the doorway.

She backs away, looking down at the ground. This has haunted me for so long and so deeply that I think about it at least once a week.

mrschestnyspurplehat

49. Letting It Rip

In third grade, I went to the bathroom, and thinking I was alone, put my hands against the wall, leaned forward, and let out a long gigantic fart. Afterward, I let out a nice big sigh of relief and pleasure. I turn around that some other kids had come in as I was releasing that massive fart. Did not look them in the eyes as I left. It’s not the fart that was strange, no matter how long it may have been.

It’s the hands against the wall, prepping my body to let it rip, and moaning “uuuuunnggghhh” afterward.

TomberryServo

50. Having a Gas

It was around date three and me and this girl were grinding with clothes on in bed, running hands all over each other. I put my hand over her throat, which unfortunately triggered a panic attack for her. I, in turn, panicked a little and did the only thing I could think to do—the very thing I had been desperately clenching my butt cheeks to try not to do. So I blurted out “DISTRACTION” and passed gas.

Octoblerone

Kids Caught Experiences

51. Jabba the Hutt Would Be Proud

When I was like 10 or 12 years old, I was in my room after just having taken a shower, when for some reason I got the weird idea to use my belt and a couple of towels to make the Princess Leia slave outfit bottom (by the way, I’m a boy). As I stood there wearing it (the front flap slightly raised since I had been thinking about Princess Leia) my mom walked right on in.

For what seemed like an eternity I saw her confused face trying to figure out what was happening, and just as she was about to ask about it I jumped across the room and slammed the door in her face. With my face bright red, I hurriedly threw on my clothes and went downstairs as if nothing had happened. My mom tried to bring it up once, but I feigned ignorance, and not another word has been spoken of it since.

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52. An “F” for Effort

My dad came with on a field trip back in elementary school. We had an admittedly attractive substitute teacher that day, and she was introducing herself to all the parents. Sub: “Hello, I’m Miss Fine” Dad: “Why yes, you are.” She immediately just walked away.

MarcusBrazil

53. There’s Got to Be a Better Way to Say “Occupied!”

I was on a train going between London and Manchester (UK) and went to use the bathroom. The toilet at the end of the carriage was disabled-accessible, so it had a wide curved door that automatically opened at a steady and slow pace—about 20-30 seconds to complete, uninterruptible, retracting in a semi-circle to allow wheelchair access to the carriage.

If you’ve traveled on these trains before, you’ll know that to close the door you enter the stall, push a button to close the door, then when it’s finished closing, you press another to lock it. Someone had not told this to the lady in the loo. Just as I arrived, another person coming from the other direction pushed the outside button to open the door and it started its inevitable arc.

For at least 30 excruciating seconds, the button pusher, myself—and eventually everyone sitting in the packed commuter carriage beyond who was facing in our direction—got to see the woman bend up from the seat, reach and hop to the other side of the cubicle and desperately pummel the door-close/lock buttons inside. Pants around the ankles the whole time.

White bottom flashing. At a merciless pace, the door opened fully, contemplated its life and then closed on the pitiful image within. The button pusher and I looked at each other, said nothing and went back to our seats.

Taswegian

54. At Least They’re a Happy Family

Sleeping over my friend’s house in seventh grade. I was trying to sleep on the floor, however, his parents decided to have very loud, wall-rattling sex. I laid there trying to fall asleep for about 15 minutes, when a loud shriek hinted that it was over…I kinda laughed a little and my friend, who I thought was sleeping, just says “I am so sorry.”

LouRebel

55. 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, and 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.

Fridge_crisis

56. The Last Dance

On our first date, this guy played Dance Dance Revolution for a good 45 minutes while I just stood there. I left and played a couple arcade games by myself, then came back and he was still playing. But it got worse. On the car ride home, he asked how many children I wanted and started suggesting names for “our kids.” Then he tried to make out with me when I got home. Nope goodbyeeeee.

EmptyMoon22

57. 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 it was even more awkward than that. Darrell was the name of the friend who had just passed. This happened in 2002 and I still think about it all the time.

20XD6_1936

58. A Hair-Raising Level of Insensitivity

I used to be a redhead. One time, in the middle of a big family reunion, my creepy uncle got super drunk and decided to loudly ask me in front of everyone “Do the curtains match the carpet?” Being a young teenager, I had no idea what he meant by this. I told him that I didn’t understand, and he loudly replied, “What color is the hair on your privates?”

Vagina_Meatballs

59. Waterworks Won’t Make It Any More Original

Once in high school, we had an assignment to write an introduction for an imaginary movie/book/play or whatever you wanted. The teacher showed us a short text as an example. The weird girl in my class used that text and read from it at the end of the VERY SAME class and we were all like “You didn’t write it, it was the example the teacher showed us just now.”

She burst out CRYING and said that we were all mean to her and that she wrote it all by herself and that it was just a coincidence that it was identical with the example. Cringed so hard.

Ms_hartwick

60. A Question That’s Hard to Stomach

This one happened to my midwife. She was pregnant with her second child, and her three-year-old daughter asked why mommy’s belly was so big. It was then explained to her that mommy had a baby in there. So she turns to daddy and asks “Do you have a baby in your tummy too?” Dad gently replies “No, I’m just fat!” A few days later, the girl is waiting in the checkout line with her mom and a very large lady comes up behind them in the line. The little girl asks the lady “Do you have a baby in your tummy like my mommy does?” The lady is kind and just says no she doesn’t, to which the girl responds “Oh, just fat then?”

notmax

61. 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.

b8le

62. Say Yes to the Dress

I once had a girlfriend come to live with me after being in a not so great situation for nearly a year in another state. I had been planning for eight months to have a dress that she had been dying to buy waiting for her under the Christmas tree when she arrived. At that time, she didn’t have the cash for groceries, let alone a nice dress; so I knew she would appreciate the gesture.

When the big day finally arrived, she got super excited as soon as she saw the box and she opened it right away. Turns out I bought the wrong dress…

N4g4rok

63. Stranger, You’re Not From Around Here!

I live in small town Iowa, where everyone is polite and reserved. One time, I took my then three-year-old nephew out to a restaurant to eat while he was in town to visit me. The man in the next booth looked very frail and had a portable oxygen tank with him. He had a coughing fit, and my nephew said, “Auntie, that doesn’t sound too good.” That part in and of itself wasn’t so bad. But then the coughing fit continued, so my nephew turned to the man and said in his thick New York accent “’Scuse me, we’re trying to eat here! Can you go die somewhere else?”

rhymeswithfondle

64. Bound in Holy Awkwardness

Recently went to a wedding where the groom had five or six different groomsmen, and they all gave a speech. First few were pretty good and funny. The last guy that went tried way too hard to make it funny. He started off with some lame cliché joke about how the bachelor party was crazy and that they’d never talk about it again.

He actually paused and waited for laughter and not a single person laughed out of over 150. Then his hands started shaking, and he kept losing his place. I think he eventually gave up after about two minutes of torture and just said, “To the bride and groom!” It was horrific.

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65. Fish Match-Maker

I was having lunch with my wife and her grandmother for the first time. We had recently gotten two fish, a black one and an orange one, and my wife was telling her grandmother about the fish. Her Grandmother lowered her voice and muttered, “You got interracial fish?” I laughed because I thought it was a funny joke. Then I realized her grandmother wasn’t laughing. She was serious, and offended.

sharkwithlaser

66. Got off on the Wrong Foot

Part of my job is processing new employees. We had this one new guy that just so happened to be in a wheelchair. He came in early on his first day, and I helped him with some paperwork. Then, he came back to my office in the afternoon and said, “I think I got off on the wrong foot with you.” Thinking that he was making a self-deprecating joke to kind of address the fact that he was in a wheelchair, I laughed and said “Good one!”

He just looked at me, blank-faced, and said, “What do you mean?” The dude really thought he had done something to make me angry earlier and was trying to apologize! I did my best to awkwardly back-pedal by saying, “That’s funny you think I was mad. I wasn’t at all!” He was still looking at me funny when he left the office.

I literally spent a week cringing every time the phone rang because I was sure I was getting called into HR.

gogogidget

67. Lost In Translation

When I was, maybe 14 years old, my family and I went on vacation to the Dominican Republic. First, let it be known that place is awesome. Such a good time. What I was unaware of though, was that it was also a huge European vacation destination. Well a day or two goes by and I’m pretty bored. All I’ve done is spend time with my family, and of course, normal 14-year-old me knows vacations aren’t meant to be spent with the family!

Finally, I see a group of English children who look to be about my age playing soccer (football) on this field within the resort. Well, genius me decides these kids are not going to like me unless I’m English. So what do I do? I decide, by god, I’m going to become English and hang out with these guys. So I approach them and it actually goes a lot better than I thought.

I end up spending most of my time hanging out playing football with these chaps. It was awesome, I legit had these kids thinking I was English, they introduced me to their (topless) sisters and mums, and I genuinely liked these people. Unfortunately, I held a dark secret that finally surfaced on the second to last day.

Pretty normal day, we’re all hanging out playing ping pong, everybody’s shouting having a good time, I’m shouting, of course in my English accent, when all of a sudden my WHOLE American family shows up behind me asking what I was doing…in front of all my new friends…..and their topless mums and sisters. Ugh, I have never felt more shame EVER…

Just seeing ALL those looks of confusion and disappointment (and of course pure laughter from my dad and sister). To this day I still haven’t lived that incident down. Eight years and they still give me heck…Make sure your American family isn’t standing behind you while you lie to a bunch of English people…about being English…

iAMtheBelvedere

68. Thanks, But No Thanks

When my girlfriend broke up with me, I was completely caught off guard. As a result, I stupidly blurted out “Okay, thank you.” It has made many things very awkward ever since.

Inesophet

69. On the Fence

In eighth grade, I tried to hop over a little miniature fence by the gym area to impress the boy I liked. Needless to say, I did not make it, and instead ripped the whole back of my pants apart, exposing my prepubescent behind to my fellow peers. I also fell forward and smacked my face into the concrete below the fence.

Needless to say, when the boy expressed his lack of interest in me to his friends, I was not surprised.

LousyMinibus

70. Monkey See, Monkey Poo

When I was about four or five a few of my cousins were over visiting and we were swimming in the pool. I always really looked up to them because they’re 8-12 years older than me and of course I wanted to emulate them. So, we’re swimming in the pool when my cousin Jonathan decides to rip a massive fart underwater.

Obviously, being the kids we are, this is hilarious and Nathaniel (other cousin) and I try to out-fart Jonathan. Nathaniel farts a few times and we busted a gut laughing and now it’s my turn to save face and become “one of the guys.” I strain and strain and a few little toots blossom forth but nothing great. The guys are really egging me on now and I start to push harder than ever in an attempt to be cool.

“At last!” I thought, as my sphincter stretches apart for what I’m sure is about to be the most epic fart ever seen by my cousins. It was poop. In the pool. I just remember laughing so hard even though my swimming shorts were housing a log of brown polonium. My cousins were in absolute hysterics. I got out of the pool, still laughing, and proceeded to tell my mother what happened.

She grabbed the garden hose, turned it on full blast, and roared, “If you’re gonna behave like an animal then you’re gonna be cleaned like an animal!” I was then blasted with 55F water. I’m 22 now and I still haven’t lived this down and I swear that this story is told at least once at every family get-together we’ve ever had since. It’s not so embarrassing now because I was so young, but I still cannot believe that I did it.

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71. That’s What I Call Smooth Steering

Driving my car through traffic. Have little trial sized hand lotion in my center console and my hands are dry-ish, so I dispense the recommended amount and start rubbing it in. Traffic moves and I have to steer, accidentally get some lotion on my steering wheel. Which is leather. Now the part I touched is shiny and the rest isn’t.

Don’t like the way that looks so I dispense more lotion and start working it into the leather. Now, this makes the rest of the leather bits look dull and pretty soon I am all in with this, lotioning whatever I can reach. Casually glance to my left, and there is a car full of people staring directly at me, eyes wide, as I thoroughly massage the interior of my vehicle like some sort of Buffalo Bill-esqe auto enthusiast.

7sundays7times

72. Too Soon

The most insensitive question that I’ve ever been asked was, “You’re lucky! Now that your father is gone, you can finally have a life of your own. Are you going to have kids?” This was asked of me by an older cousin at my dad’s wake. His newly deceased body was lying just a few feet away from us in a casket.

Wackydetective

73. 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.

Footpeter

74. Orange You Gonna Say “Woof”?

I wanted to try to drink like a dog. I put a bowl on the floor and filled it with Fanta. My dad walked into my room where I was kneeling on the floor with my tongue in the bowl. He has never mentioned it since.

fashionablypunctual

75. Are We Not Doing Phrasing Anymore?

So, I was delivering booze to a friend’s place. He was having a drunken party and I thought I’d be nice. Anyway, his buddy spills a half a tumbler of scotch down my shirt. I had to get to work so I take off and hit one of those drinking and driving stops. Of course, the officer is like, “Whew, and how much have you had to drink?”

Me: “Nothing, my friend spilled scotch on me.” Officer: “Uh-huh.” ME: “Fine, Blow me. You’ll find the truth.” Officer: “Excuse me!?” Me, thinking: “Annnd, this is how I go to the slammer.” Me: “OH! Nononono. I mean, blow me, the thing, the straw you blow into.” Officer proceeds to laugh, gives me a breath test and I blow 0.0. On with my day. Hah.

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76. The Crown Jewel of the Aisle

I was working nights at this liquor store. I step outside to smoke then I go back in and I get to stocking shelves. Well, for a reason I still do not understand, I got Jewel’s “You Were Meant for Me” stuck in my head. I have no idea why…this was in like 2004, long after Jewel’s career had peaked and faded. Anyway, I’m all high and singing Jewel…loudly…while stocking the cooler when I decide to have fun with it and sing it almost as though it was a YouTube apology video.

So now I’m cry-singing Jewel’s “You Were Meant for Me ” at the top of my lungs, when a customer pops their head around the corner and says, “Um…are you open…and are…are you OK?” Apparently, our door beeper had gone on the fritz…I tried to explain I was just stoned and fooling around…but they were having none of it and continued to look at me as though I’d lost my damn mind, not just for the remainder of that transaction, but since they were a regular for years after.

AntifaInformationist

77. Get the Scoop on Friendship

I was obsessed with the Anne of Green Gables movies when I was growing up. Anne had an imaginary friend called Katie Maurice, who was actually just her reflection. I decided to copy Anne by talking to my own reflection in a spoon. My mother walked in on me mid-conversation one day and asked me what the heck I was doing.

I told her I was speaking to my new friend. I overheard her on the phone to my dad saying, “…She thinks the spoon is her friend, Brian. Should we be worried?” I was 8/9 at the time, so definitely old enough to know that spoons are not friends.

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78. Downward-Devil

I recently started going to Church again. In January, I went to a college-aged member’s event, and while I was standing in line to get in, I started chatting with the people around me. We were talking about New Year’s resolutions and working out. One girl suddenly piped up, “But be careful of yoga! Some of the positions are for worshiping the Devil!” My reaction couldn’t have been worse.

I howled with laughter and then cracked a joke about downward dog being suggestive of a bedroom act. Unfortunately, it turned out she was very serious. She looked absolutely horrified. She stepped away from me like I was going to contaminate her, and then quoted some scripture that apparently connected to yoga.

mollsballsss

79. Inside Jokes Are Not Outside Jokes

At work (on my personal email) I was emailing my best friend who was Polish, and we often used “polak” as a joke. Me being part Italian, I also referred to “greasy Italians.” Sent the email to my friend. Then I looked again, and my stomach dropped. I realized I had typed it up in the wrong email window and had sent it to a client.

Xcopa

80. A Dead Woman Walking

My son once somberly announced to his daycare class that I had passed away over the weekend. If I remember correctly, I think he even cried too just to underscore the point. The staff were very distraught, so he must have been pretty convincing somehow. It was a severe shock to everyone there when I showed up later that day to pick him up.

AngryZen_Ingress

81. You Kiss Yours With That Mouth?

I was at a college basketball game years ago when there was a bad call on the ref’s part, and the guy like two rows ahead of me and my friends yelled out something like, “You screw your mother with that mouth?!” Like it was really weird and inappropriate and not something you’d yell at the ref because it makes no sense…and then like everyone around him just got quiet and turned around to get a look at the guy who just yelled that with a “What the heck is wrong with this guy” look on their faces.

-Words-Words-Words-

82. It’s a Big Poop After All

I took my three-year-old son to Disney World for a vacation. Of course, after about an hour in the park, both I and the offspring have to go to use the bathroom. So, we head off to one of the main bathrooms right next to the big castle. I let the boy go first. He performed a nice quick dump, complete with the customary “Good Job!” compliment from me, as we were still reinforcing the potty training mantras.

Then, I of course sit down and perform my own glorious number two, complete with a nice long “squeaky door” fart which had the offspring in hysterics. At this point, the child starts screaming out in a voice that can only be described as booming “GOOD JOB DADDY! YOU’RE THE BEST POOPER I KNOW!” This, of course, led to various chuckles from within the long line of stalls populated by other fathers. The chuckles ended up turning into outright boisterous laughter. I was so proud of my pooping abilities and so glad to finally be getting some widespread recognition for this special talent of mine.

Well, I’m a somewhat shameless person, so I clean up and go wash my hands to find that I’m now getting many nods of approval from everyone in the can who had heard the interchange. I was the best pooper at Disney World that day and was somehow both internally embarrassed and outwardly entertained at the same time. And no one can ever take that away from me.

Explodo86

83. Table Talk

Large breasts run in my family. I wear a size 30 G bra. If I’m wearing anything remotely form-fitting, I can’t hide them. I don’t like them and am actually on a waiting list for a reduction. Nevertheless, at a dinner party I threw a few months ago, the wife of a friend asked me whether they were implants. She asked me this as I was serving her food. In front of the whole table. There’s no good way to answer that…

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84. A Super Screwup

Back in high school, I had a job as a web designer at a small webshop servicing non-profit organizations. My bosses didn’t let on that I was as young as I was, and they handled all the face-to-face client meetings. My job basically entailed designing and preparing the website for our clients. One of our big clients was Christopher Reeve Paralysis Foundation.

I sliced up the site and put in filler text, knowing full well that only people coming from our internal IP would be able to see the development. I should mention that my company was small, close-knit, and had a great (albeit vulgar) sense of humor. Rather than going the standard lorem ipsum route, I did what ended up being the worst thing imaginable.

I instead filled in something along the lines of “Herp derp I’m Christopher Reeve, I drive myself with a straw. Weaknesses include kryptonite and falling off horses.” It got worse, but I’ll let your imaginations fill in the blanks. There were about four paragraphs of filler text. I came into work after school one day and all three of my company’s owners/my bosses were waiting for me.

I thought they were pulling some prank, but they asked me to come into their office. At this point, I knew something was definitely up. My boss: “Chris and Dana saw the site.” Me: “What? Who?” Him: “CRPF. Chris and Dana Reeve. The director wanted to show them the progress. Apparently he didn’t check before he showed it to him in person.”

At this point I think my stomach hit the floor and kept going straight on to the Earth’s core. My boss told me he’d let me know what the next steps were, but just to know that I was in deep, deep trouble. Anyway, I didn’t get fired (despite how adamant Dana Reeve was about that fact) and I had to write an apology to the Reeves.

I found out later that Chris actually had a pretty solid sense of humor and thought it was funny. RIP, Mr. and Mrs. Reeve.

heyitsgarrett

85. Gettin’ Freaky

I interviewed a job candidate who came in and immediately said how hot my administrative assistant was—but then, it somehow got worse. He asked if she was single or “Open to freaky Fridays.”

gmabarrett

86. A Black and White Issue

I was officiating a soccer game of 15-year-old boys. The teams’ respective colors were RED and WHITE. There was one African American boy on the Red team. As the game progressed, it got more dangerous and out of hand. At half-time, I informed both benches that I would be calling the game tight, and that the next flagrant foul would not go unpunished.

30 seconds into the 2nd half, the African American boy had a hard foul. I blew my whistle very aggressively and yelled, “TAKE A REST BLACK!” After realizing what I had said, I immediately tried to correct myself. I stumbled over every word. The damage was already done. One player on the other team said to me, “Not cool dude.”

NARLynick

87. Double Double, Toil and Trouble

When my kid was very young and just learning how to tell men from women, he liked to yell out his verdict whenever he decided which one someone was. One day, we were in a public cafe and he decided to practice. “Mama, you’re a woman!” he said. “That’s right, honey!” I replied. “And Papa is a man!” he continued.

He was pointing and talking loudly enough that a lot of people in the shop noticed and started watching. Not a problem for me, it was very cute! He began to label a couple of strangers next, talking very loudly because he was enjoying the attention. But then he pointed to an old woman across the room. “And she’s a WITCH!” he proclaimed out of nowhere.

In his defense, she was in fact dressed like some kind of an old hippie, with the kind of long flowing scarves you might expect a stereotypical witch to be wearing in some children’s book. I don’t know if she heard him say this, since I shushed him REAL fast. However, there was no question that a LOT of other people around us definitely heard and tried their best to hide their laughter and shock.

DevonianAge

88. You Crack Me Up, Old Man

First class of summer semester in grad school, we were going around introducing ourselves. Professor wanted a typical “what do you do for fun” kind of answer, and this 50-year-old IT guy just deadpan says, “I love smoking crack cocaine.” Clearly it was a joke, but it did NOT land, everyone else in the room just stared at him until he said he was kidding.

I_Febreze_Dogs

89. Director’s Cut Commentary

My mom went through this phase where she would talk out loud during movies, specifically about whatever is going on in the movie. She was also terrible at paying attention to what was going on, so often times what she was explaining was totally incorrect. In addition, she would try to talk over the movie. Mom would occasionally have to yell to make sure that she was being heard over the action scenes.

Imagine, if you will, watching the aftermath of the stampede scene from The Lion King and the person next to you in the theater yelling out “SIMBA IS SAD BECAUSE HER DAD DIED!”

BW_Bird

90. Change the Channel

You know those PA systems at car dealerships that you can hear several blocks away? The sales manager used to use them to yell at us, like even when we were inside the showroom. I’ve never seen a grown man cry at work other than at this dealership, and it would happen fairly regularly. The worst is that he would call his wife and scream the most awful obscenities at her in the middle of the showroom.

It’s hard to sell a Camry when there’s a man screaming at his wife 10 feet away.

t_vex

91. Uno, Dos…Oops

In college, I was applying for a co-op internship at some big corporate company. Of course, like all applicants, I wanted to make myself sound as appealing as possible. I decided to change “Familiar with basic Spanish” to “Proficient Spanish Speaker” on my resume. The job didn’t have anything to do with speaking Spanish as far as I knew, so I figured it was a harmless fudge.

I thought they’d never find out the extent of my Spanish knowledge was the three years I’d taken in high school. Well, I get to the interview. Everything starts out seemingly going well. Until she says, “Oh, you speak Spanish! That’s great!” She said, “We’ve been hoping to find someone to help in our South American division. Let me grab my colleague.”

Before I could respond she leaves the room and quickly returns with a woman who is clearly of Latin descent. The original interviewer says to her “This is him; he says he speaks Spanish well.” I’m sweating at this point—but it was about to get so much worse. The Latina lady looks at me and immediately starts going off in full-speed Spanish.

I could tell she was asking me questions, but have almost no idea what she’s saying. I tried desperately to remember anything left in my brain from high school, but think I just stammered, “Si” a bunch of times while smiling and nodding like an idiot. Eventually, I just said, “Sorry I’m a little rusty, it’s been a while.” She just gave me an annoyed look and left the room.

Needless to say, the rest of the interview was pretty awkward. A decade later, and that remains the only job interview in my life that I didn’t get an offer from. Valuable LPT learned that day: Don’t put anything on your resume you’re not prepared to potentially get called out on. Too bad I had to learn that the very hard way.

Inthedarkend

92. All in All, He’s Just Another Brick in the Wall

In middle school, a kid decided to don his karate wear and break a brick for the talent show. This intense music starts playing, and he comes out. Bows his head and…HIYAA! Hits the brick. It doesn’t break. Tries a couple more times. It remains unperturbed. He stomps off the stage in tears. I’m sure to console him people told him, “No one will remember this in 10 years!” It’s been more than 10 years. I still remember him as the kid who couldn’t break the brick.

pharmaSEEE

93. No Need to Be Catty

This was during my hot mess college phase. I got very drunk on a date, blacked out completely, and then puked all over my then-boyfriend (now husband)—as well as the washroom and bedroom. I woke up wearing fresh clothes. He explained everything that had happened after me begging him to tell me. When he finally did tell me, it was so embarrassing that my face went bone white.

Apparently, I started trying to exorcise demons out of him and just projectile vomited everywhere. He managed to get me to drink some water, bathe me, get me to bed, and then deep clean the room and washroom. I was so embarrassed after. The only memory I have of that night is his cat looking at me with concern and judgment.

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94. Save Some Cringe for the Rest of Us

A female friend of mine–to whom I was admittedly attracted–had been expressing her reservations about an upcoming vacation with her family. Though it wasn’t being overtly presented as such, the trip was meant as a way of re-solidifying her parents’ marriage, which had been more than a touch rocky at the time.

They would all be driving from San Francisco to a small town in Northern California, where they’d stay at a bed-and-breakfast inn for a weekend before continuing northward for some unknown destination. In keeping with the alleged purpose of this so-called vacation, two rooms had been booked at the inn in question.

To her dismay, though, my friend discovered that her mother would be occupying one room, her father would have the other, and that she and her sister would each have to bunk with one of their parents. This was worthy of lament on its own, but it was made unforgivably worse by the verbal diarrhea that I offered in an attempt at providing comfort:

“Aw, it won’t be so bad!” I told my friend. “Your father will probably enjoy sleeping with you.” A moment passed before I realized what I had said. Then, with a feeling of growing horror, I tried to explain myself. Suddenly, I made it 10 times more awkward. “Wait, I didn’t mean it like that!” I hurriedly said. “I mean, like, he’s probably sick of sleeping with your mom.”

“No, wait, I mean… I just mean that he wants to spend some quality time with his daughter.” If I had stopped there, I might have been able to salvage the situation, but as it happened, I decided that the best course of action would be to keep talking. “I can’t say that I blame him, really. I’d love to sleep with you.” She and I don’t talk much these days.

RamsesThePidgeon

95. The “G” Is Silent

I once sent a direct mail piece out quoting an Angus Reid poll. Left the “g” out, so of course, the spell-check didn’t catch it. Based on the feedback I received, virtually all those who noticed thought it was an improvement.

moirende

96. We Fell Hard…

This was early in my dating days, so I can claim awkwardness beyond human reason. It was my first date with a guy who’d I’d known and crushed on for a while before we mutually agreed we should give dating a go. So, naturally, the whole hanging-out-with-the-intent-of-romance didn’t exactly go smoothly. It went horribly, actually.

When the “moment of magic” came at the end of the date, he bobbed left, I swooped right, and he managed to fall down some steps and I fell in a bush. We called it at that and there were no more dates.

Tzulmakh

97. Automatic Responses

I can’t tell you how many times this has happened to me as I go through the checkout line. I regret it every single time. Cashier: “The receipt is in the bag.” Me: “You too.”

HeyyImAlek

98. It’s Not Technically Cheating

I had just moved to London and met this guy on a dating website. He was generally not my type, but still, I was trying to meet new people so we go on a date. As we settle into the restaurant, he takes a call from a girl and says to her, “Oh, I’m just in the pub with—male roommates name.” I can hear her on the other end getting worked up about something and him telling her to calm down.

Alarm bells are already ringing. He hangs up the phone and says, “That was my fiancé, but not a real one, just one I’m with for her visa.” At this point, I’m already thinking “bloody hell.” He continued on with his excuse, “She also lives with me,” in his two-bedroom apartment with this other roommate—cozy. “Oh yeah, I should probably tell you I’m getting married in three weeks.”

At this exact point, I just said, “Well, I’m going home,” and start pulling on my coat. His reply was even more classic: “Do you want to help me buy groceries first?”

claireinthesnow

99. 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.

HappinessIsAPotato

100. Non-Traditional Gender Roles

A few years ago, my two-year-old daughter and I were waiting in line at Nordstrom. She was being really quiet and really patient, so I decided to reward her by purchasing a Melissa and Doug stamp set as a gift. As soon as we got up to the checkout counter, she randomly blurted out to the girl who was scanning our things, “Did you know that my mommy has a [insert male genitalia here]?”

I was in utter shock and had no idea where that had come from or what she was talking about. I just stood there for a moment, expressionless, wondering what in the world had just happened, before I finally managed to awkwardly say, “Umm yeah, I don’t.” The lady just stared at me, forced a smile and simply replied, “Have a nice day.”

The only explanation I can think of as to why this could have happened is that we had been talking to her a lot about my pregnancy and discussing what gender the baby might be. We have spent a lot of time wondering whether the baby is going to be a boy or a girl, so my guess is that she was trying to innocently tell the cashier something about the baby in my belly, but just worded it very poorly.

On top of all that, all the talk about this baby’s gender must have raised some questions in my daughter’s head, because she also decided to announce to her daycare class that “My daddy decided that he wants to be a girl, so he is going to become a girl.” The daycare staff never mentioned anything about it until our daughter casually informed us of her announcement during dinner one night—and we just about died when we heard about it.

I asked her teacher the next day if she had really said this, and the teacher, in fact, stated, “Yes, she did say that. But it seemed like a very private and sensitive topic, so obviously, we didn’t want to bring anything up about it to you.” For the record, my husband is NOT transitioning and we have no idea what my daughter was trying to actually say. Ahh, kids. You gotta love them!

wickedcreative

Sources: 1, 2, 3, 4, 5, 6, 7


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