These Awkward Reddit Stories Are Equal Parts Brutal And Hilarious

September 7, 2023 | Miles Brucker

These Awkward Reddit Stories Are Equal Parts Brutal And Hilarious

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. 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 passed on the previous year from an inoperable brain tumor, and their younger son had just moved out for university. Mum starts with, "Must be nice to have the house to yourself! More time for Church!"

The conversation just  devolves from there. Mum ignores all hints to drop the subject, including the mother stating they hadn't been back to the church since their son passed. The couple were obviously horrified. I couldn't end the conversation quick enough. Afterward, my mother told me I was just being immature and had no conception of what "polite adult conversation" was like. 


2. 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…

Mistaken Identity FactsShutterstock

3. 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!"

Worst Thing Done on a Date FactsShutterstock

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.

Speak to the Manager factsShutterstock

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.

Unromantic Moments factsShutterstock

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 bare chests on the show. My mum walks in to catch me licking the TV screen where the bare bosoms were.

Caught by Mom ExperienceShutterstock

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 completely undressed.

Facts About Adam LevinePIxabay

8. 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 profanities 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.

Horrible Bosses FactsGetty Images

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 lifeless little mice, doing taxidermy on them, and then dressing them up in tiny little metal battle armor and swords to stage historical battles...using deceased mice...that she bought online. She showed me lots of pictures before the date ended.

Animals’ Biggest Power Moves FactsShutterstock

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.

Seymour Fleming FactsShutterstock

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?"

I Still Cringe factsShutterstock

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. 

Insensitive Questions factsShutterstock

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.


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.

Romantic Backfired FactsPiqsels

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…

Embarrassing Things Toddlers Have Said factsPixabay

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.

Secondhand Embarrassment FactsShutterstock

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.

Wait, You're Serious FactsPxfuel

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.

What Is My Life FactsShutterstock

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.

Obvious Romantic Hints facts Piqsels

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.

I Still Cringe factsShutterstock

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.

Embarrassing Moments factsShutterstock

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.

Significant Other Was Shutterstock

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.

Disrespectful at Home FactsShutterstock

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.

Acts of Kindness FactsShutterstock

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: " I have to stop using my smartphone, to prevent my smartphone from getting the virus?"

Self-Diagnosing Patients FactsGetty Images

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…

Embarrassing Things Toddlers Have Said factsPixabay

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.

Kids Share the Most Humiliating Acts FactsShutterstock

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.

Wedding Objections factsPixabay

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.

Craziest Things Admirers Have Done To Impress factsPexels

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.

Embarrassing Moments factsShutterstock

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 a pizza.

Strangest Thing Caught Doing FactsShutterstock

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.

Strangest Thing Caught Doing FactsShutterstock

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).

Lacked Any Self-Awareness factsPixabay

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!"

Childish Behavior From Adults factsPxHere

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.

Strangest Thing Caught Doing FactsShutterstock

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.

Awful First Dates FactsShutterstock

37. 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.

Unfair Things Teachers Have Dona FactsShutterstock

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!

Married Men Dating FactsFlickr,Roxie Rampage

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, with no clothes on, 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.

Burst Out Laughing factsShutterstock

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.

Kids Share the Most Humiliating Acts FactsShutterstock

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.

Teacher Breakdowns FactsShutterstock

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.

Secondhand Embarrassment FactsWikipédia

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.

Weirdest Date FactsShutterstock

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.

Worst Thing a Guest did factsMax Pixel

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 [illicit substances]."

Awful First Dates FactsShutterstock

46. Tyrannosaurus Toddler

My three-year-old daughter, who is normally super sweet and very empathetic, was being a total jerk 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.

Embarrassing Things Toddlers Have Said factsPxHere

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 terrible 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…

Insensitive Questions factsShutterstock

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.

Strangest Thing Caught Doing FactsShutterstock

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 toot. 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 toot. Did not look them in the eyes as I left. It’s not the passing gas 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.

Weirdest Rule FactsShutterstock

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.

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.

Never Speak of Again factsGetty Images

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.

Really That Stupid factsWikipedia

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.

Buzz Aldrin FactsWikimedia Commons,Jax House

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 intercourse. 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.”

Secondhand Embarrassment FactsPixabay

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.

Online Friend FactsShutterstock

56. 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.”

Biggest Work Mistakes factsShutterstock

57. No Need to Be Catty

This was during my hot mess college phase. I got very tipsy 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.

Awkward Job Interviews ExperienceShutterstock

58. 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.

Weirdest Date FactsShutterstock

59. 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 done. ” 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?”

Strangest Date FactsShutterstock

60. 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!

Little girl making a terrified faceGetty Images

Sources:  1, 2, 3, 4, 5, 6, 7

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