Holy Crap, I Can’t Stop Laughing At These 39 Painfully Awkward And Embarrassing Conversations

Comment exchange on social media: A user tells another to "Log off boomer." The reply boasts about online longevity and dismisses the initial comment

1. This person who got dragged in the YouTube comments:

Comment exchange on social media: A user tells another to "Log off boomer." The reply boasts about online longevity and dismisses the initial comment

2. This person who tried to start a conversation about music:

Screenshot of a Reddit discussion where a user offers payment for a video involving feet and music, followed by a mod stating a one-week subreddit shutdown

3. These parents whose son couldn’t read the room:

Screenshot of a Reddit post about mistaking parents' argument for a rap battle and joining in with beatboxing

4. This dentist’s patient who was thrown off guard:

Reddit post reads: "Dentist asked about Slovenia after staring at teeth, then refused to explain. Confusion follows."

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5. This person who saw someone’s really weird photo of their eyes:

Close-up of two brown eyes with conversation about eye color and personal preferences beneath

6. This person who learned of a new playing card:

Screenshot of a humorous online comment thread about a playing card showing "161 of clubs."

Related: 19 True Crime Cases That Were So Wild And Upsetting, The Truth Was Almost Unguessable

7. These family members who were not in the mood for someone to lighten the mood during an emergency:

Reddit post from u/AmItheAsshole about connecting an AirPod to check if it played inside their niece after she swallowed it

8. These people who came across the dumbest message ever in their online group:

A Reddit post discussing a story about a man's loss of virginity near a women's prison, questioning the frequency of such events

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9. This person who got a wild response after posting a question:

Quora question about muscle pain post-anesthesia; response suggests possible mistreatment and advises seeking CCTV footage and legal help

10. The members of this group page who found a very specific inquiry:

Reddit post asking if McDonald's can detain someone until police arrive, seeking urgent answer

11. This person who tried to explain human anatomy:

A Reddit post asks about ribcage protection. A reply describes a scenario involving a spear and a lion in a cage

12. This grandma who was sent a meme:

Social media post with a cat image and added flame effect. Text below says, "Oh my he has a headache."

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13. This person who needed a new therapist:

Hand holding a drawing of a bird inside a cage with a caption saying, "my therapist gave me this and said, 'that's you'."

14. This person who was being a respectful neighbor:

A tweet humorously shares a story about asking a neighbor if mowing the lawn would disturb the baby, to which the neighbor replies humorously

Related: 38 Photos That Went From Totally Normal To Borderline Disturbing Given What We Know Now

15. This person who gave some hygiene advice:

Summary of a social media post: A user asks for advice on removing a smell from their gaming chair, mentions trying wet wipes, and receives a comment about hygiene

16. This delivery person who received important instructions:

Phone screen showing a delivery note to leave packages at the front door, with a humorous request not to look inside during drop-off

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17. This person who just wanted to get their car battery and go home:

Tweet about a car battery costing $220. A joke follows about buying 99 batteries, totaling $23,000. The person responds with, "okay."

18. This person whose mom was on edibles:

Text conversation: Mom says her uncle gave her a gummy, hasn't felt anything yet. Later texts "hamgurber." The recipient replies, acknowledging the effects

19. This person who was sent an egregious grammar error:

Text conversation: "What happened?" "Cheating." "Who chote."

20. This person who was put on probation by their Tinder match:

Tinder chat: Person asks if the other watches "Rick and Morty" and smokes pot. Responses: "No" and "Strike one."

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21. This person who had a wildly rude DoorDash driver:

Screenshot of a text conversation about a DoorDash order involving a McDonald's bag. A comment mentions listening to Skrillex

Related: Everyone Is Acting Like An A-Hole Lately, So Here Are 50 Photos Of Absolutely Infuriating People

22. This business owner who got a review:

Review: Never been to this place, wash my own car at home. Response: Awesome

23. This person who made a typo:

Chat conversation joke; starts with "Coo" and "Thanks," followed by "pigeons when you give them crumbs" as a humorous caption

24. This person who asked for more details about a barista’s bad day:

Reddit post by Tottapola asking if they'll get fired for biting a customer's hand. Responses express disbelief and query the action

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25. This person who was feeling under the weather:

A series of text messages with a typo correction followed by "forget it" and a harsh reply

26. This person who was messaged by a customer service rep:

Text exchange joke: Someone names their contact "Joe Mama" and is asked about interest in a Nissan Rogue Sport

27. This person who was given feedback on his flirting skills:

Text conversation: "I’ve never spoken to a woman before." Reply: "No, it’s fine. You’re doing great. Just maybe don’t start with ‘bounce on it crazy style’."

28. This person who got an unexpected request from their Uber Eats driver:

Text exchange between a customer and an Uber Eats driver about cookies smelling delicious; driver asks to have some

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29. This person who encountered the world’s biggest gatekeeper:

someone asks a person where they got their food and they respond that they're not going to tell them

30. This person who found something out they wish they never had:

my wife named our son after her first love and i had no idea

31. This person who received a DM from a stranger:

stranger having a convo and then saying, it's cause i cheated so i wanted to know if he was getting even with me

Related: “We All Watched In Horror”: Former Students Are Sharing How The “Cool Person” In School Made A Decision That Altered Their Life For The Worse

32. This person who Snapchatted someone they saw on a dating app:

person figures out they searched for their snapchat from their dating profile

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33. This person who opened their phone to this confession:

i know you've probably had guys message you a lot but you make my blood pump

34. This person who came across this Tinder profile:

name on tinder is cheating husband

35. This person who got caught trying to scam someone:

someone tries to say they've been beat up and sends a selfie and the person responds, that's strawberry jam

36. This person who accidentally insulted a friend:

friend sends their new song and other responds, okay you usually have great music taste but that song is pretty shit and friend says that's my song

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37. This person who was asked out by a very, uh, creative writer:

person messaging out their every gesture

38. This person who made a very wrong assumption:

person assuming a person is being inappropriate by wearing chinese garments and the person responds saying that they are chinese

39. And finally, this person who checked on someone’s well-being:

Comment exchange: A 17-year-old post reads, "the baby sneezed, mama scared." A recent reply asks, "are you still alive."

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Also in Internet Finds: “And That’s How A Christmas Party Dies”: People Are Sharing The Most Unhinged Things That Happened At A Family Dinner, And I Have Severe Secondhand Embarrassment

Also in Internet Finds: “We See You Finishing”: 46 Hilarious Images That Scream “This Was No Accident”

Also in Internet Finds: 16 People Who Were So Accidentally Hilarious I Literally Had To Stop What I Was Doing And Share Their Posts With Everyone

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