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Article created by: Ilona Baliūnaitė

The world would be one hell of a boring place without the endless amount of awkward conversations people endure on a daily basis. When you’re in the middle of it, it’s very little fun indeed. We get it. Blushing, sweating and wanting to disappear are some of the very well known adverse effects that come with it. But that’s the price to pay for one heck of a story you gotta tell months and even years later. So in perspective, it’s relatively cheap, right?

So today, we are going on a cringeworthy trip into hilariously painful and embarrassingly awkward exchanges between individuals that have been shared by people online. Scroll down through the collection of priceless convos below, upvote your favorite ones and be sure to share your own awkward convo experiences. And if it feels like you’ve heard similarly cringey dialogues in the first seasons of The Office, it’s likely because only reality can be stranger than fiction.

#1

Screenshot of an awkward online exchange about networking etiquette and unprofessional use of smiley faces.

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Bacon Tentacles
Community Member
5 months ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

My response: In case you didn't know, "your opinion" isn't considered valid.

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    #2

    Tweet showing an awkward exchange between a writer and a barber leading to silence during a haircut shared online.

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    #3

    Tweet showing an awkward exchange at the airport where a person misunderstood TSA’s instructions and placed their face on the scanner.

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    Tweet showing an awkward exchange between a surgeon and med student about a possible perforated bowel shared online for humor.

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    #5

    Screenshot of an awkward exchange where someone’s attempt to cover a fart by dropping a textbook fails embarrassingly.

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    #6

    Awkward exchange in elevator where a man misunderstood "I love you" due to Bluetooth earphone mix-up shared online.

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    #7

    Tweet screenshot of a user sharing an awkward exchange involving mistaken identity and ice cream in a park.

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    #8

    Tweet showing an awkward exchange where a man in a cowboy hat greeted "howdy brother" and got a panicked "yee haw" reply.

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    #9

    Screenshot of a tweet showing an awkward exchange misunderstanding the name Christian as a religious identity shared online.

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    #10

    Tweet showing a humorous and awkward exchange about free beers shared during a holiday in Corfu.

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    #11

    Tweet by Hannah Durant sharing an awkward exchange about mistaking a muffin for a hamster online.

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    #12

    Tweet text about awkward exchanges when a waitress suggests wine by the litre to American customers in Canada.

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    #13

    Text post about awkward exchanges where someone accidentally screams quack while trying to say quick and fast during a missed turn.

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    #14

    Tweet sharing an awkward exchange about mistaking a mailbox with a red hat for a crossing guard, highlighting visual confusion.

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    #15

    Social media post sharing an awkward exchange at Tesco checkout that sparked online reactions about awkward exchanges.

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    #16

    Tweet describing an awkward exchange where a woman accidentally joined a wedding party in Greece, highlighting awkward exchanges.

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    #17

    Screenshot of an awkward exchange on social media where a woman forgets to bring her dog to the vet, shared online for pain relief.

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    #18

    Tweet showing an awkward exchange where a woman blew a kiss and then accidentally crashed into a taxi.

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    #19

    Tweet about awkward exchanges during a delayed flight, involving Tinder swiping and an unexpected encounter behind the user.

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    #20

    Tweet showing an awkward exchange where a therapist misunderstood a client’s childhood story, shared online for awkward moments.

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    #21

    Screenshot of a tweet sharing an awkward exchange about trying on shoes and a funny misunderstanding while shopping.

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    #22

    Tweet showing an awkward exchange where a customer replies "You too" to a cashier’s comment, sharing awkward exchanges online pain.

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    #23

    Screenshot of an awkward exchange shared online about waving at a neighbor who was actually washing her window.

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    #24

    Tweet showing an awkward exchange where a breakup at a restaurant causes people to mistakenly start clapping.

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    #25

    Text post sharing an awkward exchange involving confusing the words fee, fine, and pee at a library payment counter.

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    #26

    Screenshot of an awkward text exchange showing autocorrect mistakes shared online as part of awkward exchanges.

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    #27

    Screenshot of a Twitter post sharing an awkward exchange where a coworker misunderstood a fist bump as holding an invisible microphone.

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    #28

    Tweet showing an awkward exchange about misidentifying a friend named Trevor during a school walk, shared online for awkward moments.

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    #29

    Screenshot of an awkward exchange where someone yells at carpet cleaners, capturing awkward moments shared online.

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    #30

    Screenshot of a tweet sharing a story about an awkward exchange involving mistaken family relation during a phone call.

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    #31

    Tweet showing an awkward exchange where a child mistakes the milkman for their dad in a humorous online story.

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    #32

    Screenshot of a tweet sharing an awkward exchange about handing someone hot soup with a funny misstatement.

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    #33

    Tweet showing an awkward work email exchange where a client named Stan was mistakenly called Satan in a reply.

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    #34

    Tweet about an awkward exchange at a posh hotel involving a humorous misunderstanding about crème fraîche.

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    #35

    Tweet screenshot showing an awkward exchange about mistaking sugar crystals for glass shards on a muffin shared online.

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    #36

    Screenshot of an awkward Twitter exchange where someone misunderstands a coffee shop situation, sharing their embarrassment online.

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