'Oh, the embarrassment': 20+ Times people tried to be funny, only to have their jokes majorly backfire

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Oct 20, 2024 11:00 AM EDT

Sometimes you try your hardest to be kind and thoughtful, but you stick your foot in your mouth. It happens to everyone: to err is human! 

It's often a case of compliments gone wrong, as the 4,600+ people replying to this r/AskReddit question can tell you. The original poster of the question had their own embarrassing story weighing on them. Their coworker was wearing a Halloween costume, and this person thought they were a pumpkin. Turns out the coworker was actually dressed as a carrot! The coworker was just on the larger side… Well, that's an embarrassing mistake! Some people take these slights better than others. That person's coworker cried a bit about it, but the original poster reports that she "eventually forgave me." That's all you can do in some of these situations: beg forgiveness, act super embarrassed (you probably already are!) and try to move on with grace. 

Turns out it's not just the original poster who embarrassed themself. You can read some of the funniest stories below of people who made a fool of themselves in front of coworkers, family, or friends. 

Up next, this person took malicious compliance to the next level when they "used up every sheet of paper in our 14-story building," after their boss insisted they print 10,000+ pages! 

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  • 01
    Cheezburger Image 10416459008
    via Leire Cavia on Unsplash+

    This image is for illustration only, and the subjects are models; the image does not depict the actual subjects of the story.

  • 02
    One Halloween, I complimented an overweight co-worker on her pumpkin costume. It was a carrot costume. Reddit, when have you said/done something that you meant to be nice but made you look like a terrible person?
    via u/[deleted]
  • 03
    She was an awesome person that everyone liked, and I'm pretty sure I made her cry. She eventually forgave me, but I cringe at my own lack of decorum every time I think about that.
    via u/[deleted]
  • 04
    [deleted] Once I worked in a pizza place, had to walk through the restaurant to get to the delivery car. On my way through I saw two people I know, never spoken to them but we were part of the same crowd. As I walked past I planned on saying "gidday" (I'm from New Zealand) as I said it my brain decide to throw a spanner in the works and let me know
    via u/[deleted]
  • 05
    without warning that saying "hey" would be a better option. So basically I walk past them, look right in there faces, say "Gay!" at them and waltz out the place.
    via u/[deleted]
  • 06
    yuppitsalex In high school I worked at a place that had bowling, laser tag, arcades, etc. and in the arcade part we had this virtual reality ride that I just so happened to be scheduled at on the day this story takes place. - Anyway people got on, the ride finishes, and I go to let them out. I start to walk them to the exit, but trip as
    via u/yuppitsalex
  • 07
    I'm opening up the gate and it flies open; almost hitting the guy standing directly beside it. I'm looking down at the floor at this point, picking myself up when I say to him "Oh, sorry man. Almost took your arm off there" and as I look up I notice he's a amputee from the elbow down..... Thankfully he could tell that I was extremely
    via u/yuppitsalex
  • 08
    embarrassed (not sure if it. was the instantaneous sweat downpour, the beginnings of a nervous stuttering apology, or my face turning redder than the devil's that gave it away) and replied with "No worries, looks like someone already beat you to it!". TLDR: made an amputee joke to an amputee without realizing he was an amputee.
    via u/yuppitsalex
  • 09
    [deleted] About a week ago I was at a party and this girl I met had a large, protruding mole sticking off of her upper lip. I told her, "hey there's a bug. on your face!" and tried to brush it off. Realizing it was a mole, I apologized profusely but surprisingly she found it hilarious
    via u/[deleted]
  • 10
    njh219 I complimented a friends brother on his photo- bombing face at a Christmas party. Turns out he was autistic and he wasn't making a face. My soul hurt after that one.
    via u/njh219
  • 11
    [deleted] Oh god. Once when I was a hostess at a chain restaurant, I sat this family at a booth. I pretty much always tried to sit people at booths, because if you sat them at a table they would complain and ask for a booth anyways. So the family just stands there, and finally the obese mother turns to me and says "I can't
    via u/[deleted]
  • 12
    fit in this booth. We'd like a table, please." Afterwards one of my coworkers kindly pulled me aside and explained that we always sit obese people at tables unless they specifically ask for a booth. There's a lesson they won't teach you in the company training booklets...
    via u/[deleted]
  • 13
    MissMyCookie I once asked one of my closest friends how her mom was. Her mom had passed away about seven months earlier, but I had been away for more than a year and it somehow slipped my mind. I felt, and still feel, absolutely horrible. :(
    via u/MissMyCookie
  • 14
    Zellric I complimented my roommate for making the week's worth of lunches ahead of time. It was her supper.
    via u/Zellric
  • 15
    hardtoremember I'll just say that you never, ever ask any woman when she's due. met that day. and a fan
    via u/hardtoremember
  • 16
    xSleyah In school during Spirit Week we had different themed dress days. On "Tacky Day" my friend showed up in these loud purple jeans tucked into bright pink boots with hearts on them. I said "Oh, I thought you said you weren't doing Tacky Day!" She wasn't.
    via u/xSleyah
  • 17
    с I said 'thanks ma'am' to a guy one time.. I immediately apologized but he just laughed and said 'I thought you said "Thanks, Dude".
    via u/OperatorMike
  • 18
    chickenbowl I was at a restaurant with my family a few years ago. Our waitress comes up to us and we all notice that she was fairly average in terms of weight, but had a slight belly. Not knowing any better my mom asked, "When are you due?" Her reply was her shaking her head and quietly saying "...no." Ohh, the embarrassment!
    via u/chickenbowl
  • 19
    j. First of all, I'm Deaf. Second, this was unintentional, but I still feel like a complete It was at the ending of spring semester of college, therefore, it was almost time for summer. I decided to stop by this girl's room because she doesn't have many friends (she is a loner and overweight), so I wanted
    via u/jaxpica
  • 20
    to chime by to say hello and to wish her a good summer. She was thrilled to have my company and was talking up a storm. It was hard to follow, but I'm not too bad at lip reading. She turned around while talking and I "heard" her say, "I'm dieting for summer". So, I excitingly told her how I was proud of her for caring about her health. She was confused and I had to repeat what she said, and she looked so
    via u/jaxpica
  • 21
    uneasy and said, "no, no, I said I'm dying for the summer!" Then there was this long horrific silence, I excused myself and went and hid.
    via u/jaxpica
  • 22
    Made_In_Arlen My sister was out trick or treating with her friends. one* year. There was this woman walking down the street. She was overweight, and wearing blue jeans and a red sweatshirt. I bet you can see where this is going. Well my sister yells "Oh, it's Fat Albert!" at the top of her lungs...
    via u/Made_In_Arlen
  • 23
    My sister: Tries to compliment a woman's "costume," and ends up calling her Fat Albert unjustly. She still gets red when I bring it up. EDIT: I suppose it would be good to mention that this poor woman was just walking with her children, and was not intending to look like Fat Albert...
    via u/Made_In_Arlen
  • 24
    Lily_May This needs context: My friend is Korean and was adopted by white parents. During a college break, I was staying at his house because we were planning to leave on a trip together. I noticed a picture in his room of himself as a little Korean baby. It was kind of a derpy photo, so I picked it up, walked out, and said,
    via u/Lily_May
  • 25
    "DUUUDE, you were an UGLY baby!" Turns out his parents had adopted a child before him who died of SIDS. I just called his dead brother ugly.
    via u/Lily_May
  • 26
    n When I was maybe 7 years old I went to play at a friend's house. I tried out a new accent and said, 'This is a nice lil' ole' house you have here.' The next time I went over, despite my best, seven-year-old efforts to explain, her mother told me my friend was off limits. because I had called her house both 'little' and 'old'.
    via u/no_talent_a**_clown
  • 27
    The unfairness still rankles, several decades later. EDIT: I said it to my friend, who then repeated it to her mom once I left. So it was secondhand to the mother. Not sure if that makes a difference. I remember feeling awkward around my friend later on... I think that was my first experience feeling betrayed and narc'd on. Also, I remember the
    via u/no_talent_a**_clown
  • 28
    mother said something disparaging about my family living in an apartment and making me feel not only unfairly interpreted and sad but also like there was something wrong with us.
    via u/no_talent_a**_clown
  • 29
    I_are_God I called my teacher mommy.
    via u/I_are_God
  • 30
    [deleted] A family friend's wife had just died and we were at the funeral and a group of us decided to go to red robin's after with the widower. The waitress thought it was his birthday and brought out a little cake...
    via u/[deleted]
  • 31
    Duggur A friend once told me his grandma was probably dying, so he would be out of town for a few days without any cell reseption. I thought it would be a nice gesture to say "condolances in advance". Eh.
    via u/Duggur
  • 32
    I. I got this one, my mother recently called me to tell me my brother and his wife were pregnant and my first response was, "I'm not sure whether to be happy or sad." See they have been trying for a while and were ecstatic about the news. I literally had just woken up and thought as a single mom,
    via u/InterstellarMom
  • 33
    and sometimes it's a curse I wouldn't wish on my worst enemy. Well, my mom told them what I said and now they won't speak to me. Edit: Yes, it was an assholeish thing to say, mind you I had literally just opened my eyes to answer my mother's fifth call to me. Yes, I have tried to apologize yet, to no avail.
    via u/InterstellarMom
  • 34
    Edit 2: It has not been a long and hard strenuous road for them to conceive a child. She merely stopped taking birth control two months ago.
    via u/InterstellarMom
  • 35
    Abztekh I decided to try and be outgoing one day, as I am a generally soft spoken and awkward sort of individual, and wave at people I saw around town. I live in a pretty smallish, friendly city so it was going alright, people would wave and smile and give me "How are you"s. I should point out that people ride bikes here like it's going out of style,
    via u/Abztekh
  • 36
    and I didn't really think anything of waving at this guy riding past. Only when he didn't wave back, and instead gave me a really dirty look, did I realize he only had one arm. ONE ARM. O_o
    via u/Abztekh
  • 37
    HereForTheKit... My best friend has an older cousin who lives with her. He's always been a goofy guy, and the three of us have always said mean comments to each other in a way that means we are obviously joking. One day while I was over he comes up to me wearing a sky blue track suit that looks like it was stolen from the early 90s. It was that fuzzy velvet
    via u/HereForTheKittens
  • 38
    material, and looked absolutely ridiculous. He gave me his goofy grin and asked what I think of his duds, and I replied with extreme sarcasm "Wow, that looks great on you man," and laugh, expecting him to laugh along, but he just kinda half chuckles and walks off. Later my friend came in and asked what I said to him, because he was really down. Apparently he
    via u/HereForTheKittens
  • 39
    really liked his new outfit that he just bought, and was legitimately showing it off. I felt really bad for hurting his feelings... but man, that thing was awful.
    via u/HereForTheKittens
  • 40
    CityLetterCarri... Me(was delivering a handful of multi-colored envelopes to a customer): Good morning! Is your birthday coming up soon? Customer(somewhat elderly woman): No, my husband. just passed away, those are sympathy cards.
    via u/CityLetterCarrierAMA
  • 41
    Me: Oh....I'm sorry. She was really, really sweet about it and said that it was ok, but I still felt like a
    via u/CityLetterCarrierAMA
  • 42
    throwawaythe... I was in math class and we were all suddenly making fun of each other's clothes, just poking fun. This class was sooo boring. Anyway, this kid who is usually a big joker has this shirt on and I can't make out whats on the front. It's a small round yellow and brownish picture with small black writing under it. He had just made a crack about my tight shirt
    via u/throwawaythekey969
  • 43
    (i'm a girl) so I said "What about your shirt? I can't see whats on it? Is that a lion? It looks like a lion. Why the do you have a lion on your shirt?" I start laughing but he gets really quiet. The his friend just calmly walks over and says "DO I have to ?" I still think kick your he's joking. I have terrible far-away vision but I don't wear glasses. I laugh and say "I just want to know why he has a lion on his shirt, is it
    via u/throwawaythekey969
  • 44
    like, from Bushe gardens or something?" Nobody's laughing. I am very, very confused. His friend just looks furious. Now I think he's just trolling me (these were the biggest pranksters I've ever known) so I get up and say "Just let me see the writing, it must be from the zoo or something..." I scoot over a few seats, squint, and see it's not a lion. It's a watercolor of his (blond) cousin that was lost at sea a
    via u/throwawaythekey969
  • 45
    few months ago. It was a t- shirt from a benefit they held in her honor. At this point the room is painfully silent, and I feel like the biggest that ever lived. I just calmly say "Oh it's not a lion, it's Jenny! Sorry I have terrible eyesight." Doesn't help my case, he just goes very quiet and goes back to work. So does everybody else. I awkwardly scoot back to my chair and continue my work,
    via u/throwawaythekey969
  • 46
    feeling like I should get an of the year award. I apologized the next day very sincerely, and he forgave me, but wow that was painful.
    via u/throwawaythekey969
  • 47
    skid100 I didn't say this but my aunt did. She was a bank teller in a small town, which means they know everything. There was a new family that moved to town that she knew of because her husband worked with this ladies husband in a neighboring town. Long story short, her husband (my uncle) had shared with my aunt that the new family had adopted a
    via u/skid100
  • 48
    child years ago. The girl was now 10, and walking into the bank with her mom. My aunt, attempting to be really nice says, "for you being adopted it is such a blessing that you look so much like your mom." Girl responds, "I'm not adopted." Mom responds, "she is not adopted." Yep, she was adopted and the parents. then had to explain to their daughter the story shortly
    via u/skid100
  • 49
    after. My aunt still feels like to this day and doesn't talk about it... my mom told me when we were laughing. about how I always stick my foot in my mouth. Yeah, I don't feel so bad about mine.
    via u/skid100

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