These Horrifically Awkward Moments Made Our Stomachs Drop

April 21, 2020 | Scott Mazza

These Horrifically Awkward Moments Made Our Stomachs Drop

Everyone remembers that one extremely awkward moment where they wanted the ground to swallow them up and never spit them out again. But when it comes to “Well, this is awkward,” there are bashful slip-ups, and then there are full-on horror stories. There’s a big difference, and these Redditors have firsthand experience.

Awkward Moments

1. By Any Other Name

I asked a co-worker what his son's name was, and he answered Legolas. After two seconds of laughing, I realized he wasn't laughing. His son is actually named Legolas.

Awkward Moments FactsShutterstock

2. Tell Us How You Really Feel

I had a housewarming party and my fiancée and I invited friends over. One friend who is lesbian and had the hots for my fiancée got drunk and proceeded to tell me how worthless I am, and how I’m too fat and ugly for my fiancée in front of everybody.

Significant Other Was "The One FactsShutterstock

3. All in the Family

I once went to my girlfriend’s for Christmas in high school because my parents went on vacation. During dinner, her sister decides to announce she's pregnant. She's a 20-year-old single college student. But that’s not the worst part. Who's the dad? My 27-year-old cousin. They had met at one of our family functions.

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4. Marking His Territory

Way back in high school, my then-boyfriend was over visiting at my house. I decided to be nice and heat up some leftovers for him from the fridge. Right as I set down the plate, my dad walks in and says "That is our food." He takes the plate away from him and sits down to eat it at the opposite end of the table. I just stood there in painfully awkward silence until my dad finished and left.

Awkward Moments FactsShutterstock

5. Pregnant Pause

I saw a largely pregnant woman and made a stupid comment about "Bet you can't wait to get that out of you!" She said "Eh, not really. The baby doesn't have a heartbeat and I'm just waiting to have the still birth."

Awkward Moments FactsPeakpx

6. Not Playing Around

Playing Smash Brothers with some buddies at their house. One guy lost in a stupid way and he jokingly threw his controller away and pretended to throw a tantrum on the floor. We were all laughing at him, but then it kept going...and then his head shifted over to the fireplace and he started banging his head on the bricks and bleeding.

That's when we realized he was having a seizure and we all freaked out...

Scariest Moments factsShutterstock

7. Paging Dr. House

I was with a friend of mine and her sister in their truck. For whatever reason, we were talking about Harry Potter characters. I said "What's the name of the werewolf professor? Professor Lupus?" I was wrong, it's Lupin. Lupus, however, is the disease that killed their mother.

Bilingual Awkward FactsShutterstock

8. Too Late Now

The first time I took a bus in a new city, I pulled the stop request cord at the wrong stop. Instead of just being a normal person and telling the driver that I didn't mean to do that, I got off the bus and walked for an hour in the rain.

Awkward Moments FactsWallpaper Stare

9. You Can’t Sit With Us

When I was little, like 9-10 years old, I went over to my friend's house to chill and work on our science project. At about 5:00 just before the sun started to go down, my friend's dad called him and he told me, "One second, I'll be right back!" Jump forward 20 minutes, and my friend is still gone. Huh, that’s weird.

I go look for him, and his whole family is in the kitchen eating dinner. His dad asks me, "Oh hey, do you know your way home?" I had no idea how to respond, so I just grabbed my backpack and walked the two miles back home. I was so confused at the time as to what to do, but looking back, the whole situation was extremely awkward for everyone involved and, frankly, quite rude.

They never offered me a ride home, some dinner or anything, they just ignored me and then told me to get the heck out.

Awkward Moments FactsShutterstock

10. I Don’t See Color

I worked security at an aquatic theme park and was watching Jeopardy in the employee entrance. One of the veterinarians came through and watched it with me for a bit. He said he watches it religiously and he'd passed the test for the show and was hoping to get selected. He'd heard that they like to have a diverse group of contestants, and they hadn't had a black guy for a while, so he liked his chances.

A few days later, there are two black contestants, so when I see him leaving the next time I say, "Hey, did you catch Jeopardy last week?" "No, why?" he responds. "There were two black guys on it," I explain. He just stares at me blankly for a few seconds, and walks off. That's when I realized it was a different gentleman than I had the previous conversation with.

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11. Stranger Danger

I was watching a movie at the theater. I interlocked my fingers with the kid sitting beside me for a full minute. Turns out, he wasn't my kid.

Shia LaBeouf factsShutterstock

12. Don’t Bite the Hand That Feeds

Last year, I went to visit my friend Shirly after her brother had died. Her brother passed by suicide after running the car in the garage. When I got there, there was another girl at the house, Lisa, who was eating a plate of food that Shirly's mom had cooked. Before I got to the house, Lisa had apparently driven Shirly's dad somewhere down the street—the family didn’t want to use the car that had been in the garage with their son.

Before Lisa leaves, she asks Shirly if she can have gas money for driving Shirly's dad down the road. It was literally only a mile or two that she drove him, so it was mega stingy. But Shirly calls her dad into the room and says, “Lisa would like gas money for driving you today.” His response was just perfect.

Her dad looks at her plate of food and says. “OK, and I would like food money for the food you ate in MY HOUSE.” It was really awkward but I was proud of her dad.

Awkward Moments FactsShutterstock

13. What Happens in Vegas…

When I was 18, I went with my then-girlfriend to Las Vegas to meet her parents; we lived in Florida. I found out that her dad and mom lived in separate houses right across the street from one another for whatever reason, which was strange but definitely not the strangest thing that would happen that trip. Her dad came over to her mom's house to meet me, and I couldn't help but notice he was dressed in a suit.

I thought maybe he was just a fancy dresser. He kept asking me questions about my family and how I felt about his daughter. He seemed to like me, and we went through the trip on fairly pleasant terms. Once we get back home to Florida, my girlfriend told me the truth. She tells me that her dad thought we were coming out to Vegas to get married, and he dressed up because he was planning on taking us to get married that day.

She had to tell him that we had no intention of doing anything of the kind. Like, what?

Spencer Tracy FactsShutterstock

14. Make a Run for It

Back in primary school, I had a crush on a girl. Her younger brother was kind of a friend, so I'd hang out at their place every once in a while. But thinking it would be weird to ask if I could hang out, I'd go for a run past their place and hope they'd notice me and invite me in. It worked, but most times I had to turn back and run past at least 4 times before they'd invite me in.

I wonder how many times they actually saw me doing this.

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15. I’m Just the Driver

Once when I was 17-18, I drove a co-worker home after our shifts ended. I pulled up to her house to see her mom outside and looking up at the balcony…where my co-worker’s stepfather starts throwing entire closets of clothes out and onto a parked car. I would have assumed she would jump out and quickly say thanks for the ride to try to defuse the situation. Nope.

Instead, she stood next to my car, with the door open, essentially trapping me while she watched her parents’ screaming match ensue. I was there for 15 minutes until the authorities arrived and she finally let me go.

Awkward Moments FactsPxfuel

16. Dancing on My Own

I was talking to a friend of mine about our upcoming prom. She said that she couldn't wait to go and that she had just bought the most beautiful dress. I was a bit confused because I didn't know she was going and asked her who was bringing her. She said our mutual friend John. Now, this is where it gets really awkward.

I knew John had actually asked another girl we knew; I’d seen him ask. So I say to her, "Are you sure? I thought he was bringing X?" She looks at me with a confused expression and gets out her phone to text John. We then stand in awkward silence for what seems like an eternity until finally John replies, BUT TO MY PHONE.

He asks me to tell her he isn't going. I show her the text and she just says "Oh..." then looks at me and says, "I have to get back to my mom" and practically runs away, holding back tears. As it turns out, John asked our friend, then decided he didn't want to bring her anymore and just asked X instead, all without ever telling her!

I have never felt so awkward than when I was having that conversation, and have never been so furious at someone as I was at John.

Toxic Partners factsShutterstock

17. Open Mic Nightmare

I work at a dinner theater, and we usually do proposals where we set up a “random draw” where the “winner” comes up on the stage to win their prize, and are then surprised by their partner who proposes. It's usually sweet and makes everybody in the room all fuzzy and warm. This one guy wanted to take it further and requested to perform a song—he brought his own music and everything.

We're pretty easy going at this job, so we agree to let him do it. We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy.

It seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. Usually this gets a round of applause, encouraging the person to say yes, but not after that trainwreck of a performance. But it was about to get so, so much worse.

The poor woman was just holding her face the entire time and starts shaking her head and says "No, what's wrong with you?" She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on mic is "Well, that's that."

The guy ended up staying for the rest of the show and had many more drinks. That was years ago, and it still remains one of the cringiest things I've ever seen.

Awkward Moments FactsShutterstock

18. Trading Places

I dated a girl named Chrissy for a year back in college. Her parents were divorced and she lived with her mother and never spoke fondly of her dad. I got the impression that he had cheated and that's what led to the split. About nine months in, I finally meet Chrissy's dad while helping her twin sister move. It…did not go well.

I had dark, emo-ey hair, a lip ring, visible tattoos, and it was obvious that he didn't like me right off the bat. He acted like a jerk to me the entire day, enough to where Chrissy and him got into a huge fight over dinner over it, prompting us to leave midway through. He called her cell 10 minutes later and threatened to cut her off if she didn't break it off with me immediately. This is not the awkward part. This is the awkward part:

Eight years later, he's a client of mine and we get along incredibly well. He has no idea I'm the same guy who dated Chrissy.

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19. Slip of the Tongue

I got on an elevator with a woman, and she had on these really nice boots. So I complimented them by saying "Nice boots." She then cups her breasts and says "Well you're not shy, thank you, they're real." She immediately realized I said “boots,” and it was the longest elevator ride ever. To this day, whenever I say boots in any context, I do so with a very hard, deliberate “T.”

Awkward Moments FactsShutterstock

20. Joke’s on You

I was hanging out with a friend and we ran into someone he knew a from a while ago. My friend asked the guy, “How's Jerry doing?” The guy replies, “Oh he's dead.” Me? I just stood there in silence.

Awkward Moments FactsShutterstock

21. A Delicate Matter

I was getting a sonogram and they sent in a 60-year-old lady to do it. It was clear that she had retired from somewhere, then ɡone back to school so that she could be a sonogram tech and "look at bаbies" all day. She seemed so furious thаt she was going to have to sonogram ѕome 25-year-old dude's nether regions.

As ѕoon as she walked in the room she had a scowl on her face, and when she opened my chart to see what was going on, she was immediately upset. Ѕhe was trying to rub that petroleum conduction jelly between my thigh without actually touching or moving anything. Ѕo I politely moved my you-know-what out оf the way like any gentleman would dо. Bad move.

She got all flustered and ѕhouted, "Don't touch it!" I've never been so mad and embarrassed at the same time.

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22. VIP Dinner

I dated a girl for three years in college and lived with her for two of those years. Her father had never liked me and never really talked to me. I was a year older, and after graduating I stayed behind a year to live with her while we figured out our future. The week of her college graduation, her extended family was in town to celebrate.

They had two fancy dinner reservations two nights in a row. Work prevented me from going the first night, which I was invited to, but the second night I hadn't been invited. My girlfriend called her aunt, who had made the reservations, and was told it was an oversight and of course I could come. That…did not turn out to be the case.

The night of the dinner, my girlfriend’s mom and dad show up to pick her up. I walk out with her and we get in the car. Her parents were obviously whispering very quickly with each other as I walked to the car, then they say “Uh... so you're coming? We only had reservations for a set number.” My girlfriend explains how the aunt added one to the reservation, and we get in the car and start driving.

My girlfriend had brought along some picture albums to show from a trip, and they were too big for the back seat where we were, so we stopped a ways down the road and I got out and put them in the trunk. As I'm out of the car, I see that the father is talking very fast to my girlfriend and her mom. I get back in and the father starts driving super slow.

Finally, he stops at a stop sign, puts the car in park, and turns around to look at me. He says "This is a family dinner. You aren't family. You weren't supposed to be invited." I sit there in silence for what seems like forever but was probably 15 seconds. I say "Uhh…should I get out of the car?" he says "Yes."

I get out, and he speeds off. I then walk home. As it turned out, they never made it to dinner. My girlfiend stuck up for me, and her father hit her. He said she had to break up with me or he'd never speak to her again. And he was the kind of guy to follow through on that sort of thing; he had already cut ties with most of his family for stupid reasons.

The next day, she graduated from college, came home, and broke up with me.

Tipping Point in Relationship factsShutterstock

23. Daddy’s Little Girl

The most awkward thing to ever happen to me is still something I have a hard time thinking about. This girl called me "Daddy" during intimacy…all with a picture of her dead father staring at me on the wall.

Online Friend FactsShutterstock

24. Me-Ow

I was at a bar with the girl I'm dating and her roommate when I received a text from a good female friend of mine from high school: She was in town and wanted to meet up. I invited her to join the three of us for drinks. When she shows up, she gives me a big hug and starts talking to me intently. My date's roommate quickly misinterprets the nature of our friendship.

She looks at my high school friend and says right out, "I think it's pretty obvious you aren't wanted here, so you should probably leave." Now, my date and I looked at her in disbelief as if we couldn't believe that just came out of her mouth. My friend, however, was quick to respond. She downed her drink, stood up from the table and said, "Well you're fat and ugly, so I win," and walked away.

Awkward Moments FactsPxHere

25. When One Door Closes…

I went to my neighbor’s house on the Fourth of July with a big box of fireworks I had bought in Pennsylvania. We were drinking in his house for a bit before his mom showed up with his grandmother. They were outside on the porch, and I was on the other side of the glass sliding door preparing the fireworks to bring outside and downing a beer.

I finish my beer and grab the box to go outside…and step directly into the screen door, which I hadn't realized was still closed. I mean, I go completely through it and tear the door off the hinges, all while screaming obscenities in front of his mother and grandmother. They don't let me drink at their house anymore...

Awful First Dates FactsShutterstock

26. Toe-ing the Line

One time in college, I was standing in the elevator in my dorm and this girl just stares at my feet and says "You have really nice toes." Oh, but it didn’t end there. I saw her in the elevator a couple of weeks later, and she says to me, "Hey, you're the guy with nice toes."

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27. Privacy, Please

I'm a cam girl, and my dad walked in on me when I was doing a cam show.

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28. Putting on a Show

After having my second child, I went to the craft store to buy art supplies. As I lifted my youngest child into the cart at the front of the store in clear view of the street and the cash register with waiting customers, my three-sizes too big pants fell to the floor, revealing my granny panties. My two-year-old son let out a howl and pointed at me.

I quickly collected him and ran to hide at the back of the store. After a while, I made a mad dash, paid for my stuff, and got the heck out of there.

Worst Kids FactsShutterstock

29. Shake Hands With the Devil

I was at a job interview. I went to shake the hand of my interviewer, and somehow I managed to grip only his index and middle finger. Yup. Just think about that for a second. Try it on a friend some time and see how awkward it is. Then think about doing that in my situation. I absolutely hate thinking about that moment.

Instant Karma factsPxHere

30. Like Water for Melons

One time, I saw watermelons at the store in a big box labeled "19 cents." I (stupidly) thought this meant the watermelons were 19 cents each. I put eight in my cart. Imagine my surprise, then, when the cashier rang up my watermelons for thirty-some-odd dollars. Baffled, I just stared at him and realized it was nineteen cents PER POUND.

I was too awkward and embarrassed to tell the cashier I misunderstood or changed my mind, so I just accepted my watermelon-y fate. I ate watermelon for breakfast and lunch and dinner. I made watermelon margaritas and watermelon sorbet. There isn't a watermelon recipe on Pinterest I didn't consider.

It was halfway through the watermelon fiasco, after complaining about the stupid watermelon for days, that I realized that even if they HAD been only 19 cents…it still would’ve been too many watermelons.

Eating Sins FactsShutterstock

31. I’m Not a Regular Grandma, I’m a Cool Grandma

I’m a girl. My grandparents, both in their late 80s, invited me to come down to Florida for spring break one year, and they said I could bring a friend. I was thrilled, and so was my friend Marie. She and I booked our tickets and were really excited for our trip. About a week beforehand, Gram called me to talk logistics.

What kind of food should they have for us? What kinds of things would we like to do? Would we be wanting to share a bed? She kind of slipped that last one in there, and I told her that Marie and I are not gay. I'm pretty sure she didn't believe me, because every morning at breakfast while we were there, she told us about how there were several gays at her church and they were wonderful.

It was the cutest thing, but so awkward—especially when my WWII vet grandpa, the strong and silent type, chimed in his acceptance.

Awkward Moments FactsPikrepo

32. Jiro Dreams of Service

So, my family and I have a trip to Japan. We hear about this amazing sushi restaurant so we, of course, decide to give it a try. We keep getting the directions mixed up because we're directionally challenged, but finally find our way there around 9 pm and get a seat and menus. My dad tries to place our order, but one waitress, in particular, keeps brushing us off each time we try to order.

We sit there for thirty minutes trying to order our food before my dad just blew up. He grabbed a waitress and started screaming at her in English. "We are customers; treat us like customers" or something like that. Everyone is staring at us by that point and my mom and I are trying to just melt into our seats.

The poor girl bursts into tears and the manager is called. Turns out, my dad grabbed the wrong waitress. We manage to place our orders with a different, trembling waitress, choke down our food—I think it was as good as they said—and get the heck out of there.

Awkward Moments FactsPxfuel

33. One Sick Puppy

I had a girl in high school tell me that no one would date me because I am too much like a puppy, and no one wants to sleep with a puppy. This would be hurtful but not that weird…except that she then followed it up with, "But I sleep with puppies…"

Memorable Overheard Comments FactsShutterstock

34. Let’s Play Ball

I was homeschooled and then put into a public school softball team at around 13 or so. I had never played games with other kids and wasn't allowed to watch TV, so I didn't know ANY rules or how the game worked. I just ran around when people yelled and tried to take the ball from people when I could from time to time.

I ran the bases when I was supposed to be at one. I stole home plate. I threw the ball to the outfield. Those poor kids probably thought I was disabled.

Awkward Moments FactsPixabay

35. Mother May I

I had been friends with this guy for nine years. We were both sophomores in college, and he was home for Christmas break staying with his parents. We had recently discovered that we had feelings for each other, but decided we didn't want to date long distance. But, while he was home, we wanted to spend time together.

We were with a group of friends but decided to go back to his house, just the two of us. He had asked his parents earlier in the day if he could have friends over. Well, his parents already disliked me. My brother had dated their daughter and broke her heart. Whoops. So I show up at their house, with them expecting a group of people, and it's already awkward.

Then, my friend and I spent a couple of hours in his basement making out. By this time, it was pretty late (around 1:30 am). He went upstairs to get his keys to drive me home, and when he came back downstairs his eyes were really wide, and he said, "I'm so so sorry!"

Apparently his mother was still awake and refused to let him drive me home that late. So, she decides it would be better if she drove me home. It was a 20-minute drive, and the car was completely silent.

Awkward Moments FactsShutterstock

36. Don’t Put a Ring on It

I worked in a resort hotel, high end, waiting tables in the fine dining restaurant. It was pretty common for people to propose there, so much so that I had a system for the whole thing. One guy came in and wanted to do the ring in the champagne thing, and I talked him into doing a dessert alternative that doesn't result in a sticky ring and champagne on the floor.

But when I bring the ring, the woman bursts out with: "Darn it, I've told you before I'm not marrying you." He flips, she's super calm about it and basically treats him like a child having a tantrum, which to his credit he was not screaming or anything, just very upset. He left, she ate the dessert, eventually, he came back and paid and they left together.

Super awkward.

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37. When Nature Calls

When I was 14, I had a boyfriend named George. Being 14, all we ever did was make out and watch movies together, and his dad was cool enough that sometimes we would have some of George's friends over too. One day, George and I were chilling out with our mutual friend Steven, watching TV and whatnot, when his dad walks in and says, “You guys just watching TV then? Well, George, I think I'm going to call Old Mary.”

So, about 10 minutes passes and someone comes to the door and they go upstairs. George then turns around and says casually, “Old Mary's a sex worker, by the way.” The look on our faces must have been rather special. I think we sat through about five minutes of the dodgiest sounding bedroom noises before making excuses to leave... what a messed up father-son relationship. Old Mary.

Online Friends FactsShutterstock

38. There’s No Accounting for Taste

I dated a woman for about a month. One day, we are sitting on my couch making out. Suddenly, she just stops, turns to me, and says, "I am not attracted to you. I'm sorry." Then leaves. That one was hard to get over.

Change Life FactsShutterstock

39. Netflix and Not Chill

My brother and a lady friend came inside our house. I asked him where his girlfriend was because her bras were still in the laundry room. He then informed me that they had broken up a month before and that this lady was his new girlfriend. Well, you see…I had already invited his ex over to watch movies with me that night.

When she arrived, everyone stood there in awkward silence for about a full minute. Everyone left pretty quickly. I am a female and didn't know they'd broken up. But why did she say yes??

Henry VIII FactsShutterstock

40. Food for Fought

I was working at a wine bar when a married couple sat down on a pretty slow night. I went over the specials and they ordered. Once appetizers came out, the man thought it would be a good idea to serve his wife divorce papers. I did my best to avoid that side of the bar for the rest of the night, but I did bring out tissues for the wife, who was breaking down.

The guy paid, but I do not envy that ride home.

Janet Leigh factsShutterstock

41. Taking One for the Team

I tooted once while going to eat with my girlfriend's family. It was silent, but the smell was animal, mixed with rotten eggs and a pinch of kimchi. Anyway, I just knew I was busted. However, when her dad said, "Oh dear lord, who did that?" I remained silent and then, inexplicably, the girl says, "I did it." I think that's when I finally understood what love was.

Catherine Howard FactsPickPik

42. Welcome to the Family

My parents invite my boyfriend to the house for Thanksgiving dinner. This is a BIG. DEAL. for me, because I'm male, my coming out wasn't exactly the easiest thing in the world, and I had been with this guy for three years by that point and it was really serious. I was so proud of my parents that I could burst.

Parents were on the couch watching TV. I bring him in, make the introductions and...nothing. They say hello. They ask how the drive was. But that's it. Nothing. They don't even get up. They just keep watching TV. I understand that they might've been uncomfortable or whatever, but my Dad—one of the most generous and friendly people ever—doesn't even get up to shake his hand.

Dinner the next night was equally awkward. Almost complete silence, and when they did talk, it was to my sister and I. Neither of them made an effort to engage him in the conversation at all. Last summer, I brought him home to help me and my mom pack up the house, and she was much friendlier and talked and got to know him. But that first time...not only was it awkward for him, but I was also painfully embarrassed and peeved at my parents.

Awkward Moments FactsShutterstock

43. You’re Not You When You’re Hungry

I was standing in line at my college cafeteria checkout, waiting until it was my turn to pay. The guy in front of me in line looks to be purchasing only a Snickers ice cream bar. He makes eye contact with me and smiles slyly. From there, he raises an eyebrow, lightly tosses his Snickers in the air so that it flips twice, catches it, and gives me a knowing wink. This was the end of the interaction.

To this day, I have no idea what that display was about or how I was supposed to feel.

Worst Thing Done on a Date FactsShutterstock

44. I Scream, You Scream

I worked at an ice cream parlor that was kind of old-timey. Not much seating. Anyway, the guy comes in with a girl, they pay for their own cones and take a seat at two of the seven stools. Dude is talking and the girl is laughing and into it. TWO HOURS LATER, DUDE IS STILL TALKING and the girl looks like she wants to cry or punch him in the face.

They withstood the gale-force trauma of at least seven families with screaming kids, adults who "just love that these tiny places still exist," and several rounds of me sweeping around their feet and pointedly scrubbing the counter around them. The guy never asked her a question. Never let her say more than a few words before he stomped out her "rude interruptions."

I was all, "Hey guys, we close soon. I hope you have a nice day, but I need to mop." Watched them walk down the street and he was STILL TALKING. Like, get a room with yourself, guy. You're obviously the man of your dreams.

Weirdest Date FactsShutterstock

45. Funny Meeting You Here

I was at a club, and the room we were at was lame, so I walked over to what seemed like another room in the club. I am walking with these three girls behind me, and as I am crossing over to the room, this other guy is walking opposite to me. We kind of do that stupid dance when you run into someone in the hallway or whatever.

I laughed, so did he, then I thought "Why the heck isn't he out of my way yet?" Then I noticed he was wearing the same shirt as me. It was a freaking mirror.

Shouldn’t Have Done That FactsShutterstock

46. Open Bar

I went to a really swanky Mardi Gras event in Louisiana as a guest and didn't know that the buckets of drinks were ordered per table because people were up and dancing. So I grabbed a drink from a table and was sitting nearby. Suddenly my wife nudges me and says, "That dude at the drink table is seriously peeved looking at you." I just froze up for some reason, like do I face him or just awkwardly stare in every direction but his for the rest of the night?

I chose the latter. I felt bad and just left the drink where I sat, unopened after like 30 minutes. If I had just gotten up, apologized, and given it back while explaining the mistake, it would have been no big deal. But as each minute passed, it just got worse and worse. I still think about it while I try to go to sleep sometimes and the cringe keeps me awake...

Awkward Moments FactsPeakpx

47. Do You Really Want to Hurt Me?

One day when I was in kindergarten, there was a girl who I had a little crush on. At least as much of a crush that a five-year-old can have, I suppose. The teacher summoned us to the floor area, where she sat on a chair to read to us. I wanted to sit next to said crush, but she wanted to sit next to her friend. What did my rational five-year-old mind do?

Cry. Yep, I bawled my eyes out because she didn't want to sit next to me. Naturally, the teacher stopped and asked me what was wrong. After my blubbering story about her rejecting me in front of the whole class, she forced the girl to let me sit next to her.

Parenting Lessons BackfireShutterstock

48. Always Destroy the Evidence

One of my best friends had a radio show on our university's station. I liked a guy in one of our classes, and my friend and I thought it would be clever for him to interview me off-air about my interest in that guy. We then put the interview on a disc and gave it to him. Well, the feeling was not mutual. I graduated five years ago and I'm married now, but this still makes me cringe so hard.

Wendy Williams factsShutterstock

49. Who’s the Jerk Now?

When I was a young kid, my family was sitting around talking about a relative and how humorous she was. They always kept saying how she was always "Goofing off." I suddenly got the bright idea to contribute. So I entered the conversation by saying: "Or jerking off!" I somehow got the notion that jerking off meant being a jerk—I had no idea what it really meant and I had probably never heard the phrase before.

So when my family looked at me with the biggest eyes I had ever seen, I tried to back it up by saying, "You know? Being a jerk?" Eventually, my aunt realized that I didn't know what it really meant and said, "Uh, yeah." Then the silence arrived. I still cringe to this day.

Kid's Home Life FactsShutterstock

50. So You Think You Can Dance

A friend wanted me to find a date for the formal our fraternity was having. I asked a few girls and they had other things to do. So I called the girl who I usually danced with at a few dances. She picks up the phone, I reply who I am and ask if she wanted to go to the winter formal that was coming up. I overhear her say to her roommate, "It's that stupid boy who always asks me to dance." She agreed.

Fast forward a few months later, and I got introduced to her roommate. As soon as I can, I tell her, "I was the stupid boy who kept asking your roommate to dance."

School Trips FactsShutterstock

51. It Runs in the Family

Back when we were 17 or 18, my boyfriend and I were in his room one day, just watching movies and chilling. His mom walks in and asks to talk to him, they both go out into the living room, and she proceeds to rant at him about how it's not normal for us to spend so much time together, and how she didn't like that we had been in his room all day.

Meanwhile, I'm alone in his room, and can clearly hear the whole conversation. I gather my nerves and all my stuff, walk out to them, and say, "Matt, I'm going home, would you like to come over to my house?" The mom interrupts with, "We're actually having a conversation here," so I just say goodbye and walk out the door.

His sister, who thought the conflict had somehow been initiated by me, then made it ten times worse. She chases me out of the door screaming, "YOU WITCH, YOU RUINED MY FAMILY!" I was pretty shocked by this and didn't respond; I just got in my car and drove home. A few minutes later, my boyfriend shows up to apologize for his family.

It didn’t end there. A few minutes after that, there's another knock on the door. Yep, his mom had followed us to my house and asked to talk to him outside. He told her to go home. This all happened a few months before we both moved away to university, so I just didn't go to their house again. We're now in our 20s and still together. His family is still crazy and he agrees.

Luckily, we now live five hours from them.

Caution to the Wind factsShutterstock

52. Adventures in Babysitting

I used to babysit a three-year-old when I was in high school. It was her birthday and her dad invited me. I bought her a stuffed snake, since she was into snakes, and some helium balloons, and showed up a few minutes early in case the parents needed some free babysitting while they set up. I get there, and nobody is there except the mom and the three-year-old.

So I play with her and supervise while the Mom ignores I exist, which is cool; she scares me anyways. About an hour goes by, things are getting a bit awkward, nobody is showing up. I'm in their house being in the way, but leaving now would be rude, so I wait around. Finally, kids and family show up, the kids are upstairs, all these adults are sitting around the living room.

And nobody acknowledges I am there. I smile and try to say hi but people just look away. So I stand in a corner by the stairs waiting to be thanked so I can leave. And about another hour goes by, me just standing right there in the corner of the room, about five feet away from everyone, awkward as heck.

The dad shows up and he stands right next to me, staring into space, sipping a beer. I try to chat with him, but he just nods and stares off into space, ignored by the rest of the people as well. Finally, I'm thinking "screw this, so I announce I have to go, everyone just stares for a second, then turns away. So I just walk out of their house. No thank you, no bye, no hello, no offer of food or drink, no offer to sit down.

Never forgot it.

Dumbest FactsShutterstock

53. Fairy Tale Wedding: Ruined

My husband and I paid for our own wedding. We got married at Disney, with very few people invited, since we could only afford something small. That suited us both fine, as neither of us are very close to our extended families. Well, my husband's family decided to rent a house and throw us a party a couple of days after the wedding, which is a very nice gesture.

The not-so-nice part was when they explicitly stated that my family was not invited. I just assumed they were and mentioned that they might come, which was when I learned how wrong I was. Needless to say, I didn't want to go to the party. I'm a bit asocial to start with, and rejecting my family was a pretty big no-no on their parts, so why would I want to?

I'm sure some people will understand why they chose to not invite my family, but when you get right down to it, it was just plain rude. I had to beg my brother to go with me, as I wasn't comfortable walking into that without some sort of support. My husband loves me and supports me, but it's not fair for me to put him between his family and myself.

Online Friends FactsShutterstock

54. Are You Negging Me?

On a very awkward date, the guy asked me: "So, at what age did you start wearing tampons?"

Twins FactsShutterstock

55. Special Day

I was eating at a restaurant and heard the hostess ask a couple she was seating if they were out for anything special. The husband replied, “No, it’s just our anniversary.” It has inspired my father-in-law to drop that line almost any time he goes out to eat now.

Valentine’s Day Disasters FactsShutterstock

Sources: Reddit, , , , , , ,

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