You know that awkward moment when someone says something stupid and you laugh… and then you realize they were being 100% serious? Here are the internet’s most awkward “shouldn’t have laughed” moments.
This piece is based on an AskReddit thread. Link on the last page.
I met a guy who’s studying engineering with me and he mentioned to me he’s part of the flat earth society.
I laughed at first but he didn’t laugh with me. We ended up having an hour long debate. No matter what I said, he wouldn’t believe me and I learned he believed in almost every conspiracy theory out there.
2. A helping handout.
An old roommate wanted me to start paying more in rent because he was trying to save up to buy himself a house.
3. They’re taking the hobbits to Isengard.
I asked a coworker 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.
4. MK Ultra creepy.
I went on a date with a dude in high school and he told me that he had astral projected himself into my dreams for the past few weeks to “groom” me sexually for him.
I dont know man.
5. What’s in a name?
My friend told me that she was naming her daughter Bunny Petunia.
I just laughed and said “Can you even imagine how much she would hate you if you did that?!”
I felt bad but I decided to go all in with the honesty and tell her that Petunia sounds like a reasonable name (even though it reminds me of the awful aunt in Harry Potter) but that a 35-year-old woman named Bunny might have a hard time being taken seriously by her peers in a professional setting.
6. Seize the day.
Playing video games 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 wall.
That’s when we realized he was having a seizure and we all freaked out.
7. Twice bitten.
When my daughter said she had been stung by a bee and it went all of the way through her. It turned out she had been stung on the chest and back at the same time.
8. Now THAT’S a product placement.
A girl I was seeing told me she didn’t believe in dinosaurs.
Her issue with dinosaurs wasn’t so much creationist denial as much as it was a belief that they were a marketing scheme companies invented to sell dinosaur toys. Also the toy companies must’ve planted fossils, because how else did they get there?
A couple weeks later I got her a dinosaur doll. She got really mad and was like… “That’s what they want!”
9. I don’t think, therefore I am not.
I dated a girl a few years back. One day we’re chilling at my house, and I ask her if she wants to watch a space documentary. Her response blew me away.
She said she “doesn’t believe in space.”
She was 100% convinced that the sky was all their was and that space was a huge cover up by the government or something.
At first I laughed, then we argued and I couldn’t win because I haven’t been to space to prove it exists.
We didn’t see much of each other after that.
10. I consider myself a North American.
Someone once said to me, “Wait you’re Chinese? I always thought you were Asian.”
11. Dead silence.
Was hanging out with a friend and we ran into someone he knew from a while ago. He asked how another friend was doing.
My friend: How’s Jerry doing?
His Friend: Oh he’s dead.
Me: Hahahahaahahaaah! Ohnothatwasntajoke
12. The rain in Spain.
On Wednesday, a customer asked me why our produce section was so empty, especially in terms of stuff like lettuce. I told him that it was because of extreme weather in Spain, where we source most of our stuff from. He cut off my explanation with, “Why does it matter what’s going on in Spain. We’re in America?
13. Trigger incident.
I used to teach drama camp (ugh). I would take suggestions from the kids on Monday, write a half-hour play based on those suggestions that night, and then they would perform it on Friday.
I once had a parent come to see me after reading the script. Turns out she had found a whole new way of being offended.
She asked if there was a way to do a play with no conflict in it. I laughed, assuming that she was poking fun at the other overly sensitive parents I had to deal with.
But no, she meant it. She wanted us to tell a story without any obstacles or confrontations. I then carefully explained to her that a story without conflict would not be a story, but just a series of occurrences.
Man wants pizza. Man goes to fridge. There is pizza in fridge. Man eats pizza. Theatre!
14. Shoulda gone to the flea market.
Worked at a pet food store. A woman came in and asked where to put topical flea medicine on her kids. I laughed way too hard. She complained to my manager, who also laughed.
15. Bleach blond.
My uncle asked my brother if he thought our other brother bleached his butt.
My brother, telling me the story:
“I kept waiting for him to start laughing or smile or anything, but he just stared at me with such a straight face. I was like ‘oh you’re serious? I don’t know dude. What was I supposed to say?”
16. Keep on rocking in the free world.
I work as a server in a restaurant. We use little wooden trays as check presenters and since it is an open air restaurant we weigh down the receipts with decorative stones (shiny ones like for the bottoms of fish tanks). I dropped a check for an older couple and when I got back the man said, “You should warn people that those rocks aren’t chocolates! I could have broken a tooth!” I get a lot of older people who like to josh around with me so I definitely thought he was kidding.
He was not. He was actually mad at me because he had tried to eat the rock and it was obviously my fault.
17. Punch and Judy.
I was at work one day with a couple of other people and we had a shift manager that liked to fake fight and punch people for fun.
One day, one of our coworkers came to work and announced that she was pregnant. He thought it was a funny joke, ran up to her and punched her right in the stomach. She was furious! Thankfully the baby turned out perfectly fine.
18. There are two kinds of drunk…
A man was regaling his fellow party-goers with his drunken jokes. He described being found as a newborn in a field, after his teenage mother hid her pregnancy and gave birth at home. All he knew about her was she was a Waffle House waitress. We sat there, enthralled, waiting for the punchline, until we realized he’d moved from “life of the party” onto the “in vino veritas” stage of drunkenness.
19. The watered-down version.
A co-worker mentioned that she thought milk was too rich, so she poured herself a glass of water, and added two of those little cups of non-dairy creamer.
This was almost two years ago, and I still don’t know what to think.
20. It was an inside job, man.
This one girl asked me if 9/11 really happened on 9/11 or did the news and others SAY it happened on 9/11 because it sounded more legit than any other day. Ive never heard a 9/11 conspiracy quite like that one.
21. Better call the toe truck.
I was taking a long leg cast off a kid about 2.5-3 years old. After I get the cast split open and pull it off, mother says, “Oh, his toe fell off.” I’m like, “heh, nice one.”
The kid was in the cast because his small toe had been nearly amputated and reattached; the doc was hoping what tissue was still connected would be enough to vascularize the distal portion. It wasn’t and the kid’s toe had indeed fallen off.
22. High steaks.
I was at a steakhouse and as always, it was the birthday for a girl across the table. She was there with her mom and probably a good friend. Anyway, once the table realized it was her birthday and we all wished her a good day, she asked me how old I thought she was. If I were putting money on it I would have said 13, but I figured she’d feel good if I said I thought she was a bit older, so I guessed 16. She got mad”and said “No! I’m 20!!” I laughed. She didn’t.
23. Can we get a doggie bag?
I was a waiter and guy said his wife wanted to go home with me. I had never heard of anything like that before.
24. I’m a triangle-earther myself.
I met a guy who’s studying engineering with me and he mentioned to me he’s part of the flat earth society.
I laughed at first but he didn’t laugh with me, we ended up having an hour long debate. No matter what I said, he wouldn’t believe me and I learned he believed in almost every conspiracy theory out there.
We’re still friends but we don’t mention politics or anything like that anymore, he’s also a Trump supporter despite the fact that we live in South Africa.
25. When God closes a window…
First day on a new job, my boss was discussing standard office policies. He said, “And I’d like to point out we have an open door policy here.”
I said, “Oh, great! So if I have a problem I can come to you?”
He said, “No, I mean keep your office door open at all times.”
26. Definitely a miscommunication somewhere…
When I was 18, I went with my then girlfriend to Las Vegas to meet her parents (we were in Florida where she lived with her aunt and uncle). 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, but nothing else happened of any note.
Once we get back home to Florida, my girlfriend decides to tell 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 getting married in Vegas.
27. Just looking out for her phone’s health.
I used to have an elderly patient I just loved because she was just a jolly, sweet old lady (and she might have brought me some food, from time to time). She was the type of lady who just barely understood technology, so she got a smartphone and tried to stay up to date with everything that was going on.
One day, she comes by the clinic saying she’s sick. I examine her, just mild symptoms of a common cold, nothing too serious. I tell her that she has an infection and this type of infection is treated without antibiotics because it’s not a bacterial infection but a viral infection. She understands that part, but then she asks me:
Her: “So, I have a virus?”
Me: “Yes, ma’am. What you have is a virus infection”.
Her: “So… do I have to stop using my smartphone, to prevent my smartphone from getting the virus?”
At first, I smiled because I thought it was a joke and I found it cute but she was dead serious. Like, she was concerned that she couldn’t get her smartphone close to her mouth because her viral infection might spread to her smartphone and get hacked. I told her it was a different kind of virus, that her smartphone was going to be fine.
28. Maybe he should, erm, read a book?
I worked at a bookstore and a customer asked why the hardcover and paperback versions of the same book didn’t cost the same amount.
I chuckled and said, “I guess I’ll have to look into that.” He came back to me 5 minutes later and asked if I had found out yet.
Met a guy, and I told him my name. He said “I’ll probably not remember it; I have memory problems.” I said, “Haha yeah, I’m bad with names too.”
Met him again two days later, and I remembered his name. He, on the other hand, didn’t remember meeting me. And when I realized it wasn’t a joke, and was told by his mother that he actually does have memory problems, I felt like a jerk.
30. He was definitely in the dog house…
Mine was a Facebook message. One of my animal shelter buddies messaged me some text and two pics. I didn’t scroll up to the text. I only saw the one pic, which was a very funny looking dog. It was a chubby chihuahua that had a very bewildered look on it’s face.
I replied “LMFAO”.
A couple hours later, I looked again and scrolled up and saw the text. It was about this guy who died and she was trying to re-home his 2 dogs and included 2 pics. To which I replied LMFAO. So, I’m a jerk. I tried to explain and apologize but I still think she’s a bit upset about that.
31. The hands-free joystick.
I was hanging out with a couple of friends one day. We were just talking and we ended up on the subject of our first time pleasuring ourselves.
One of my friend begins his story. First thing he told us was that for the first two months after he started, he did not use his hands. We thought he was joking until he gave us a dead serious look. All of us immediately asked how did he get off with no hands. He described that he would sit down and use his thighs to stimulate himself until he would finish.
To this day the saying “look mom! no hands” has a completely different meaning to us.
32. Paul, Simon, Paul Simon…they’re all the same.
I was at an engagement party two weeks ago. An old friend from home I haven’t seen in a long time. School friends I haven’t seen in years.
Was mingling a bit and spotted my old friend Simon. Now I moved away four years ago so I decided to go up to Simon and say hello “it’s been a long time” etc.
Walked right up, extended my hand, “Well Simon man, it’s been ages, good to see you!”
“I’m not Simon.”
“What? Of course you are.”
“I’m not Simon.”
“You’re messing with me?”
At this stage I turned to the other two old friends standing beside us. “No that’s not Simon. That’s Paul.”
“Nah, you’re messing with me.”
“We thought you were joking, man. That’s Paul.”
It turns out that in our rural area of five or six villages there are two people, completely unrelated who are basically doppelgngers Simon and Paul.
I could see his face slowly start to tense up as I kept forcing the issue. I was adamant this was Simon and this guy gets this a lot apparently.
It finally clicked and the cringe flooded over me. I still replay the exchange in my head weeks later and groan.
33. The math checks out.
I own a small electronics design business (30 employees). A part-time intern working 20 hrs a week and making about $15 an hour came to me and said, “I have to cut my hours back to 10 a week – so I’ll need for you to double my salary.”
Yeah, no. Have a nice life.
34. Ouch, that’s tough.
My dad telling me he didn’t like gay people. I was gearing up to come out to him, and was testing the waters, so to speak, by raising the topic in conversation. I did not expect him to be against it, because he’s pretty dang liberal on almost all other issues.
35. Honesty is the best policy.
My now boyfriend and I were on our fifth date. We were out to lunch, and some toddler started throwing a screaming fit. Boyfriend and I looked at each other and I said something along the lines of, “Kids are the best, aren’t they?” Which is when he said, “Oh, I’ve been meaning to tell you, I have a daughter.”
We have similar humor styles so I started giggling thinking he was teasing. He was not. So that was interesting.
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