Sometimes it’s difficult to tell if someone is joking or being completely serious about something; especially of that person is usually the joking type. In this article, people share the most cringeworthy “Haha, oh wait, you’re serious?” moments.
[Source can be found at the end of the article]
A couple of months after I left my last job I heard that my ex-boss’s wife was divorcing him. He was a bit of a hot head when I worked for him, not very flexible and generally a bit mean towards me, but I didn’t hate him for it or anything. It was part of the reason I left though. I end up going for a drink with a group of my ex-colleagues and in his drunken state my ex-boss asked if I wanted to know what his ex-wife had written on the divorce papers. Obviously I said yes and he told me she’s filed for divorce because he was unreasonable. I laughed in his face as he’s literally the most unreasonable man I’ve met. The deadpan look he returned made me realise he was deadly serious. Felt pretty bad for that.
When I was in middle school there was a period of a few weeks when kids would fake seizures to get a laugh. It was the hip thing to do. So, I was at the mall toy store one day and I came around the corner of an aisle and saw a kid a little younger than me on the ground, absolutely killing it.
I delightfully shouted, “DUDE, YOU ARE GOOD!”
I’ll never forget his parent’s faces when I looked up and figured out what was really happening.
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 Scotland!
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). 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, 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.
I work in a deli and we had a new older lady start. I was showing her how to display the chicken breast and she turns to me and says “I’m going to have to work up to the chicken, my ex used to tie me up and hit me with raw chicken breast.” this was so shocking and out of the blue I assumed it was a joke. So I laughed. But nope, turns out she had just gotten out of an extremely abusive relationship. I just thought she was grossed out by raw chicken.
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.
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.
Oh well, he doesn’t remember me laughing at him.
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.
It was very well known in high school that I was gay. I can’t remember the details but my friend made a joke about it. My table of friends and I all laughed. The teacher walking by stopped and shouted “Matthew! You can’t call someone that. That’s disgusting!” We all just stared at her and you could see in her face the slow realisation. She never apologised.
Broke my arm real bad once. Went to Urgent Care… the doctor there said it was a ‘hairline fracture’ and didn’t even need a cast!
So I laughed. Considering my hand was stuck in a downward position, could barely move my fingers, and the bone was visibly pressing against the skin of my arm.
Turns out she just didn’t know anything. We went to an actual orthopedist and he freaked out and had us in for a surgery the very next morning.
Have not been to any Urgent Care since.
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.
When I was engaged to my husband, we were talking about baby names and he said if he had a daughter he wanted to name her Whitney. I laughed and said “Oh God, you mean as in Houston?!” and he sombrely said “No, as in my cousin who died of cancer at 16.” I felt really bad for joking about it because I totally knew about his cousin and it slipped my mind.
Thankfully we had boys.
I was at work, I work in retail, and me and my coworkers heard a loud BOOM, but we didn’t think anything of it.
5 minutes later, an older lady who is in the store almost everyday, maybe in her 50s-60s, came up to me and said “I just drove into your building.”
I looked at her, and right before I began to laugh out loud, I realized she actually did.
Meet and greet with my new police chief. I’d been law enforcement for a few years in another part of the country.
She introduces herself, and proceeds to tell us that our first goal, our highest priority in every call, every encounter, is to make her look good.
I laughed out loud, and then realized that she was mad-dogging me.
My quarterly evals for the entire first year were not encouraging.
On my 25th birthday, my new-ish boyfriend told me he was going to “surprise me” and do something special as a birthday dinner. He told me to get dressed up and wait for him around 7. I was super excited to wear a dress for once, got all dolled up and was eagerly waiting for him. When he showed up, he was wearing jeans and a T-shirt and just holding a grocery bag with store-bought sushi. I laughed, thinking this must be a pre-cursor to the actual ‘big night out’. Nope, we just ate store-bought sushi in my living room. It was actually a pretty nice time but he shouldn’t have hyped it up so much.
Part of my job is in-processing new employees. Well, we had this one new guy that just so happened to be in a wheelchair. So he comes in early in the day and I help him with some paperwork. Then he comes back in the afternoon and says “I think I got off on the wrong foot with you.” So thinking that he is making a self-depreciating joke to kind of address the fact that he’s in a wheelchair, I laugh and say “haha, good one.” Then he just looked at me blank faced and said “What do you mean?”
The guy really thought he had done something to make me angry earlier and was trying to apologize. So I did my best to awkwardly back pedal by saying “That’s funny you think I was mad.” I literally spent a week cringing every time the phone rang because I was sure I was getting called into HR.
This happened just yesterday. I take AP world and the AP euro teacher was walking by. I’m hanging out in the hall with some friends and they’re line “Hey, how’s the toe doing?” and he responds”I’m gonna find out tomorrow if I keep it.” I start laughing cause he’s normally a pretty funny guy and makes a lot of jokes. He just gave me this really weird look and walked back to his room. He actually got bit by a brown recluse and there was the serious possibility of losing his toe. I felt terrible afterwards.
I used to be a waiter and I’m pretty sure this guy was here with a prostitute but I ignore it and continue doing my job. Later on I go to the table and say, “would you like any desert?” To which the woman replies “No he’s going to eat me later.” I laughed and then they both weren’t laughing and I just walked off.
One of the students in my class got in a minor car accident and was in the hospital just in case to be checked. He missed 2 classes so the second class we asked the prof if he knew where he was and he replied “He’s dead.” The prof was known to make weird comments like that as a joke so about half the class thought it was a joke and laughed. Turned out the guy actually died after he got home from the hospital.
My best friend since kindergarten just announced that he’s changing genders.
When he told me, I thought he was making some elaborate joke with me like he does often. I didn’t buy it fully until he came over to my house and slept over. I woke up in the morning and he was in the bathroom. When he came out, he had full makeup and a dress on.
That was when I went “Oh, you’re serious…”
Still my best friend, I don’t care what she does, as long as she’s happy. She has nothing but my full support and I’ve been helping her every day get a little bit better with her transition.
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.
I was at a Kobe Steakhouse (Teppanyaki, like Benihana’s) 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. Then I realized she was serious. Now every time my friends and I go to Kobe Steakhouse, we bring it up.
I loved my Dad. I just feel the need to say that ahead of time. My Dad lived a very hard life, never learned to read, worked with his hands his whole life to provide for my mom and I.
One time when I was about 15 we were watching Jay Leno and he was doing Jay Walking. I was talking about how funny it was that people could be that stupid. I said “Can you believe there are really people in America who don’t know how many stars are on the American Flag?” My Dad kind of chuckled and then said “There are 52, right?” I cracked up, thinking it was a joke, and then I finally stopped to see the look on his face and realized he was serious.
I felt like an absolute jerk, because I knew he was hurt, but I just really never imagined he was serious. I learned a pretty important lesson that day about judging people and being careful what you say that might hurt someone.
Her: How do we even know that Dinosaurs were called Dinosaurs if they’re all dead now and we’ve never met one in real life?
Me: Hahaha that’s funny.
Her: What’s funny?
Me: Oh honey…
It took me literally half an hour to even get her slightly on board with the fact that things are called things because we decided on the name not because things inherently have a name we discover.
I wish I was joking.
Dated a girl for ~4 months a few years back. One day we’re chilling at my house, ask her if she wants to watch an episode of Brian Cox’s documentary Wonders of the Universe to which she told me she “doesn’t believe in space.”
She was 100% convinced that the sky was all there was and that space was a huge cover up by the government or something like that.
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 eachother after that.
Playing Smash with some buddies at their house. One guy lost a game 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…