25 Attempts at Humor Gone Wrong

Oh, uh, may she rest in peace…
25 Attempts at Humor Gone Wrong

There’s an old adage that laughter is the best medicine. The thing about both medicine and comedy, though, is that it’s only effective when used properly and in the right dosage. An unfortunately-timed joke will not only kill the mood, but the cringey silence afterward will make everyone in the room mentally queue up the Curb Your Enthusiasm theme song. 

To that end, here are a few times Redditors tried to be funny but didn’t quite stick the landing… 

GroseJoy2theWorld . . 6y My newest boss at the time had accidentally brushed my butt with her hand and said sorry I didn't mean to. I didn't have my work-filter on so I naturally teased her a little with a wink and a sure. She got really flustered and uncomfortable. I don't think it had anything to do with me but a week later she quit. ... 3.3k
OctoSash . 6y I've only tried to use yo mama jokingly twice in my entire life. Both times, the person's mother had died unbeknownst to me. ... 1.6k
Satyrane 6y A girl had what looked like a little spot of bean dip on her upper lip, and I jokingly said that she kinda looked like Hitler. She started crying. Turns out it was a permanent scar that happened recently. Another time I saw a girl crying at a party, and I just said Hey, it's okay. Guys are dicks. It was kinda my go-to before this when I saw crying girls at parties, and it usually cheered them up. Turns out her boyfriend just died in a car crash. So anyway, that's why I never talk to people
el-toro-loco . 6y I was at a party, and a girl behind me was talking with a mouthful of food. I couldn't understand her so I said, I could have sworn I just heard one of the adults from Charlie Brown. A few people laughed, and I didn't think much about it. Later on, the host of the party told me that she has a speech impediment. ... 2.5k
Heinrich-The-Dork 6y During my first ever interview for a job, my would-be boss asked me: Have you ever been convicted of a crime?. At this point, all the questions had been straightforward and all my answers had been as well. I decided that it was necessary to show off my charismatic side by telling a joke, and decided that there was no better time then right there as a response to his question. I said: Well, I was once arrested for attempted murder. Interviewer: Wait... What? Me: Yeah, I had two crows and was trying to get a third. I
cecebeme . 6y This guy I work with showed us a picture of a buff shirtless dude on a motorcycle and said, this is what I want to be one day. So I said wow it's going to take you a long time to turn yourself into a motorcycle and he gave me the most evil look. It was around other coworkers as well and only a few people laughed about it. It was so awkward with how offensive he took the joke. ... 1.3k
mallardman57 . 6y It was early in the season and my coach didn't really know everyone's name and background. Us kids knew each other pretty well, however. We began practice and he noticed our motivation was low and we kinda moped through the drills even the fun ones. Half way through practice he finally said, come on guys what's wrong? You all look like your mothers just died. Well turns out a week ago ones of our teammate's mother had died of cancer leaving her devastated family behind. So yeah, that was pretty awkward. ... 2.2k
ChiefBigwilly 6y My ex girlfriend had made a new friend at university and wanted to go out to town with her, so I called up my mate and we all went out together. While we were in the pub, I made a joke about incest. I can't quite remember what the joke was, but it made sense with the story. My mate laughed, but my ex and her new friend were stone silent. My phone vibrates about a minute later, I check it to see a text from my then girlfriend. The text read her parents' are cousins you fucking
Fatcatattack94 . 6y I was at a suicide awareness function where there was a local band playing music. The lead singer almost dropped his guitar and said .. .. oh my guitar just tried to commit suicide.. yeah..... not many people laughed....... ... 294
Zeckamaniac 6y My pregnant wife and I were at a wedding reception and were talking to a friend of ours we hadn't seen in a few years. She was complimenting my wife on her baby bump and I jump in trying to be funny. You can have it if you want. I don't really want another one to deal with. Too much work. She awkwardly smiled and kept on talking to my wife. Little did I know that she had a miscarriage less than a month prior. Egg on my face. ... 349
nevergettingoutofbed . 6y At the ER where my 5 year old cousin had previously passed away. My whole family was there, crying about her sudden death. After a few hours my grandma announces we can all go to her house for sloppy joes. That was my favorite thing my grandma cooked and without thinking I screamed YES!! With a huge smile on my face. It was really uncomfortable after I realized what I had just done.. ... 139
GangsterGatsby 6y Some army recruiters were talking to my high school class about enlisting. They were describing how they don't take anyone and when coming up with examples of inappropriate tattoos, one of them pointed to our foreign exchange student and said, So if you go out and get a face tattoo of a swastika, you won't be able to join the army. Well the recruiter didn't know that this kid was from Germany. The whole class went quiet and then burst out laughing, while our teacher informed the recruiter that this student was German. The student took it pretty
saintraywood 6y I met a German guy who said he was raised in Lancaster. I joked, You know, you've got the handsome looks of a German. You have a jaw like a Nazi propaganda poster. Karl was not amused... nor were his friends ... 141
SteveHeaves . 6y I was leaving a bar one night and the door guy was kind of air dj'ing to the music, which I thought was kinda funny, so I went along with it. I said, Ah cool! Air DJ!, and mimicked scratching turntables. This caught him off guard, and he turned and said, Uh, what? It was at that point it became painfully obvious that he had some kind of muscular disorder and couldn't help it. I said, Oh, nothing! and quickly noped the fuck out of there. ... 23
AsaEx . . 6y A few days ago my boss told me I could go home early because we were slow that day. I said something along the lines of okay, as long as this didn't happen again. The next day he calls a meeting and everyone's hours are cut back. 40
 6y ... I witnessed SUCH an awkward moment at my last place of work. I worked with an Indian lady who came in one day complaining that her wrist was hurting. We were all offering our sympathies when suddenly another work colleague stood up, in front of about 70 people and shouted, 'It must be all of that curry you're always stirring'. Then after about 30 seconds of really awkward silence we just heard her whisper under her breath... 'I probably shouldn't have said that, should l'? Nothing like a little bit of casual office racism on a Monday
 6y ... My brother, cousins, and I used to pretend curse because we weren't allowed to actually curse around our parents. We would say things like, Suck my dic (long pause) tionary. Our parents would complain and we would say, I was just saying dictionary. That's not a curse. Obviously, the only way for it to work is to end the sentence with the curse word. My cousins were joking around during Christmas dinner. One of them said, Shut up and put your dick in my mouth. Не meant to end his sentence with the curse word so he
theunluckychild . 6y I broke my back ~12 weeks prior and was still pretty sick and wheelchair bound. So I was out with a group of friends whom I hadn't seen since the accident. They asked Where do you want to sit? I simply deadpanned and went I can sit wherever. I thought it was funny but a few of them went white as the wall.
mypubertyhurts . 6y It was me. I used to work at a cinema and for a couple weeks some newbies from another branch came along so we could train them up and whatnot. I'd been training 3 or 4 of them before going on lunch, where I went to Nando's. While waiting for my order I noticed that the staff were training some newbies too. Always one to try and not be awkward, I quipped up some small talk with the waitress by saying So, I see you've got some slaves too?. She stared at me in shock, and that's
Novah11 . 1y In genetics class the prof was putting a funnel full of fruit flies to sleep with gas, and as the Drosophila started falling to the bottom, I said They're dropping like flies! The room went silent. A classmate said the word groan. Не got a chuckle. ... 41
hansentj . 1y When my wife was giving birth and in the middle of a big push she peed all over the doctor camping out between her legs. I was scared out of my mind at the time and uncomfortably blurted out hey, some people pay good money for that. My wife didn't laugh. The doctor didn't laugh. The nurses didn't laugh. I'm still ashamed 12 years later. ... 11
wookiepubes23 . . 4y One time, while working at a doggie day care, during our morning meeting the boss said I've never talked so much about humping and pooping and my reply was we had very different experiences in high school..... The whole staff just stared at me like I just dropped a baby ... 3
MonstersAbound 6y Was woken up at 2am by the doorbell. Took a little while to become conscious and actually realise it was the doorbell by which time my wife was awake as well. I go down to see who it is. It's a neighbour, as soon as I open the door he tells me there is a fire next door. Next door is a building site and a small digger was currently ablaze. Slightly concerning as gas canisters were stored on the site. I rush back upstairs and my wife has looked out the window and could see the fire
JJGerms 6y A few months after the space shuttle exploded in 1986, we had an assembly at our school from the folks at NASA or somesuch. We knew there was gonna be a Q&A after and we started goading our pal into raising his hand and telling one of the many space shuttle jokes that had been going around for months. Specifically, this one: How many astronauts can fit in a Volkswagen? Two in front, two in back, and seven in the ashtray. Q&A comes up and we are needling buddy. Come on, man, raise your hand. Well he finally
Rocketmax 6y Had just got seated for dinner with my wife when the teenage waiter stopped at the table next to us to ask the older couple if they needed anything else. The woman asked for a to go box and then got up to go to the bathroom. When the waiter came back he said something along the lines of here is your box the husband says naw her box is so much tighter and tastier than this one. It was like time stood still, the waiter had no idea what to do, the old man thought it was
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