Posted on Jul 28, 2021

75 Of The Most Painfully Awkward Exchanges In All Of Human History

I keep scrolling and I keep cringing.

Dave Stopera

by Dave Stopera

BuzzFeed Staff

1. The café convo:

Tweet about a guy at a café who farts when he thinks the music is loud but realizes he's listening to music on his iPhone

2. The tortoise convo:

Tweet reading "My mum was too embarrassed to tell the vet our tortoise was called voldetort so she just said his name was Susan"

3. The grandma convo:

Tweet reading "When i was 12, i was signing a birthday card for my grandma and i wrote 'You're a great grandma' and she lost her shit because she thought i was telling her i was pregnant"

4. The bread convo:

Redditor responds to question "Servers of Reddit, what's the most awkward date you've seen unfold": "I once saw a guy shake his dates hand when she reached over to grab some bread"

5. The Gordon convo:

Tweet about someone sending a close-up of Gordon Ramsay's forehead instead of their cleavage, and laughing that someone is wanking over Ramsay's forehead

6. The grandpa convo:

Text conversations where someone says "i don't think my grandpa is going to make it" and someone responds "What is he making"

7. The gas convo:

Tweet about someone passing gas very loudly and a boyfriend taking the fall, and that's how they knew he loved them

8. The gas station convo:

Tweet about someone learning to mind their business after asking a guy in a car why he's letting a woman pump gas, and the guy points to his wheelchair in the backseat

9. The phone bill convo:

Tweet showing a text conversation with a Verizon worker who thinks they are being flirted with after asking for the customer's PIN and being told "CUTE"

10. The barber convo:

Tweet reading "trying to forget the moment this afternoon when my barber asked 'are you having fun?' and i said yes but he was talking to his daughter who was filling in a coloring. book"

11. The guitar convo:

Tweet about someone recalling how they unknowingly played guitar loudly on their patio while a neighbor was grieving a loved one

12. The eye contact convo:

Tweet about someone making eye contact and waving at the person giving them oral sex

13. The cowboy convo:

Tweet about someone wearing a cowboy hat in a public bathroom and saying "Howdy brother" and the person responding with "yeehaw"

14. The birthday convo:

Tweet about a dad asking their kid for their phone and passcode, and giving it back when told it's the kid's birthday

15. The crème convo:

Tweet reading "my bf told me when he was 17 he worked in a posh hotel and at breakfast some bloke asked him 'is this crème fraîche?' and he replied 'yeah we don’t serve out of date food' and I can’t stop thinking about it"

16. The bathroom convo:

Tweet about a woman opening a pad while in a bathroom stall in the men's bathroom by mistake and being told it sounds like she's eating snacks in there

17. The library convo:

Tweet about someone asking to add them on Facebook and then rejecting the request

18. The breakup convo:

Tweet reading "I broke up with my girlfriend at a restaurant and she started crying, everyone thought i had proposed so they started clapping"

19. The lab convo:

Tweet reading "my lab partner said 'hi i'm christian' and i said 'hi i'm muslim'; christian is his name"

20. The Poland convo:

After waving in response to someone who was waving at another woman, person pretended to be hailing a taxi, which drove them to the airport, and now they're in Poland starting a new life

21. The cropped convo:

YouTube comment about getting cropped out of a photo taken during a date

22. The dentist convo:

Tweet: "Screaming, just hugged my dentist thinking he was going in for one but really he was just taking off my dental bib; don't think i can ever recover from this"

23. The fist bump convo:

Tweet: "a cute guy i worked with wanted to give me a fist bump; i thought he was pretending to hold an invisible microphone so i leaned forward and said hello"

24. The surgery convo:

Surgeon asks during surgery if someone farted; when there's silence, surgeon says "I need to know because I may have perforated bowel"; med student says "I farted"

25. The hamster convo:

Tweet: "i saw a girl carrying a hamster so i asked if i could pet it but it was actually a muffin"

26. The elevator convo:

Tweet: "The elevator doors opened up and a guy walked in the elevator. It was just me and him in there and he said 'I love you," and I’m not rude so I said 'I love you too" — he gave me a weird look and pointed at his Bluetooth"

27. The Subway convo:

Tweet: "i once walked into Subway, asked for a 'mootball feetlong,' said shit, then walked out; I can never go back"

28. The customer convo:

Tweet: "Meant to say 'hold on for a second' and 'give me a minute' to a customer and it came out as 'hold me for a second'; what a Monday"

29. The soup convo:

Tweet: "One time i went to hand someone a bowl of hot soup and my brain tried to say 'careful it's hot' and 'here's your soup' so instead i blurted out 'careful, it's soup'"

30. The surprise convo:

Tweet: "I surprised my girlfriend at work this morning, came up behind her and kissed her neck; she laughed and said 'Mike stop you know we're at work'; my name is Brandon"

31. The hugging convo:

Tweet: "tonight i walked past a couple fighting on a street corner and my tipsy ass yelled 'just hug it out' and the girl replied 'you wouldn't if your sister was due with your bf's baby now would you becky"

32. The networking convo:

Adam Karpiak @Adam_Karpiak

I hate networking

03:14 PM - 30 Sep 2020
Reply Retweet Favorite

33. The dating convo:

Text of someone texting 20 people at once to scam them

34. The hamster convo, part two:

Tweet: "Accidentally just replied to a boy I fancy off my hamster's instagram account"

35. The receipt convo:

Tweet: "yesterday at target the cashier said 'your receipt is in the bag' and i responded with 'you too' so i've been dealing with that for the past 18 hours"

36. The server convo:

Person tweets that they need a job where they don't interact with people after they brought a bday table decoration to a table celebrating their dead dad's bday

37. The number convo:

Tweet: "Dude asked for my number while I was cashing out and I said I'm not interested, and the guy says 'I meant for the rewards program'"

38. The cheese convo:

Tumblr post: "Apparently my mom is not even home and the person i hear puttering around the house is the carpet cleaning service; I've been yelling 'Grill me a cheese' at them for 20 minutes"

39. The driving convo:

Tumblr post: "My friend was driving and we were almost past our turnoff so i tried to say 'quick' and 'fast' at the same time and ended up screaming 'quack'"

40. The airplane convo:

Person who was bored at the airport started swiping through Tinder and hears the guy behind them go "ouch hard no for that one?" and it's the man they just swiped no on

41. The bank convo:

A person who works at a bank says to a lady who comes in with a $150,000 check that they'd like one of those, and the woman says "it's a life insurance check; I would rather have the person"

42. The dating convo:

Person who told a date they had to leave to catch the last subway runs into the person 15 minutes later while walking out of McDonald's eating a Big Mac

43. The deer convo:

A person's 5-year-old nice says the blue deer on their shirt is a boy deer, and after the person says it could be a girl deer, the niece says, "I said it's a boy because it has antlers"

44. The sneeze convo:

Person who tries to avoid sneezing in the store ends up farting, peeing, and coughing violently

45. The Dick's convo:

Tweet from a worker at Dick's: "Today a woman came up to the register with 2 kayaks to buy; after ringing them up, i looked her dead in the eye and said 'would you like these in a bag?'”

46. The pizza convo:

Facebook conversation in which a guy opens his pizza upside down and thinks it doesn't have any toppings because he was high AF

47. The other library convo:

Text: "I had to go to the library to pay a fee and I was practicing in the car between 'I have to pay a fine' and 'I have to pay a fee' and I walked in and firmly stated 'I have to pee'"

48. The cone convo:

Tumblr post: "I MEANT to say 'oh crap, I left my phone in my car,' but what I ACTUALLY said was “Ah, my fart cone"

49. The dressing room convo:

Tumblr post: "today at work i let someone into a dressing room and they said thanks and half of me tried to say 'you're welcome' and 'no problem' and i ended up saying 'your problem'"

50. The Transportation Security Administration convo:

Tweet: "I was at the airport and the TSA agent said 'scan your license face down,' so i put my face on the scanner and waited"

51. The password convo:

Tweet of a mom asking her son who he lost his virginity to because it's his security question

52. The family convo:

Tweet: "My bf met my family for the first time and we were playing catch phrase and his word was boner; instead of skipping it, he said 'something that Bridget gives me' right in front of my father"

53. The "crisps" convo:

Tweet from someone who got a sandwich and chips at a store, and the guy at checkout asked if they want to go for a drink, and after responding that they're flattered but have a fella, the guy says "no, it's part of the meal deal"

54. The divorce convo:

Tweet: "in college i went to a therapist for the first time and he asked me to tell him about my childhood; i got to 'and then my parents got a divorce' and he echoed 'your parents got you a horse'"

55. The red wine convo:

Tweet: "When my sister in-law was a waitress in Canada, she was taking drink orders from a group of Americans who each ordered a glass of red wine; she suggested they choose a LITRE instead, so one man raised his hand and said 'I’ll be the leader'”

56. The Starbucks convo:

Tweet: "I blanked when i got to the counter at Starbucks and said 'vodka soda' and she said 'huh' and i said 'huh' until I remember I was there for coffee"

57. The hours convo:

Tweet of a person who screenshot their response to their boss's request that they work a shift tomorrow — "will someone tell this bitch to shut up?" — and accidentally sent it to them

58. The craft store convo:

Tweet about a girl's boyfriend confusing the store Michael's with an actual person and getting jealous

59. The professor convo:

Tweet: "I emailed my professor and meant to say 'I am worried I don't understand some material on our next test,' but I accidentally sent just 'I am worried'"

60. The fart convo:

Facebook post: "Today in class I had the urge to fart, so I had the bright idea to drop my textbook at the same time, but i dropped my textbook, everyone looked at me, then i farted loudly"

61. The food truck convo:

Tweet reading I am at a food truck and this guy walks up and says ”I'll have my usual” and the guy working says “I don't know who the hell you are"

62. The Maribel convo:

Tweet of someone thinking the text "I'm making you come at 12 on Friday" is from a hookup and not their boss

63. The tripping convo:

Facebook post: "Accidentally tripped an old lady, meant to say 'i'm so fucking sorry' and 'are you ok?' What came out was 'Are you fucking sorry?"

64. The hospital convo:

Text from a wrong number about a man named Jake setting his butthole on fire

65. The cancer convo:

Someone tweets "I'm cancer freee!!!!!!!" and someone asks "How tf do you change a zodiac sign?' and then apologizes

66. The innocent mother convo:

Tweet of a mom who thinking ass eating season means it's icy out

67. The NCAA convo:

Tweet from someone who just finished a drug test and "asked Mr pee pee watcher what's the largest penis he's seen on the job; he looked me up and down and said 'a lot bigger than that'"

68. The psychiatrist convo:

Tweet of a person replying "peepee poo poo" to what they think is an automated text but is actually from a behavioral health doctor

69. The freshman convo:

Tweet about someone being in the wrong school on orientation day

70. The vet convo:

Tweet about a lady forgetting to bring her dog to the vet

71. The toothbrush convo:

reddit story about a person drinking out of a glass of water grandma used for her teeth

72. The grapes convo:

Text of someone sending a picture of grapes and then "Consider this a fucking warning; oops, sorry, wrong person"

73. The exam convo:

Snapchat of someone who thought their teacher wrote "salsa" on their exam but they wrote "59/59"

74. The app convo:

Tweets about someone confusing phone apps with appetizers in a question about recommendations

75. And the Helen convo:

Wrong-number text from a woman named Helen freaking out about a someone's child's behavior at a barbecue

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