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15 Haunted Twitter Users Confess Their Most Awfully Awkward Conversations

This collection of cringe-packed conversations was inspired by Jimmy Fallon asking Twitter what their most awkward texts were. The results are filled with regret and fails and even innocent laughs. 

wrong number FAIL cringe Awkward phone conversation ridiculous texting funny - 7947269
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Man Takes Awesome Revenge On Abrasive Freeloader Trying To Purchase His Leaf Blower

In this wonderfully irrational display of a choosing beggar ultimately coming to terms with the fact that people don't enjoy getting bossed around, amidst negotiation. Bring a spicy, unreasonable, and arguably emotionally abusive stance into a talk about buying something; good luck, my dude. Sounds like the jerk in this scenario, ultimately gets what's coming to him, and that is nothing. 

freeloader cringe conversation ridiculous texting cheap funny choosing beggar - 7697669
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Women's Texting Conversation With Mom Looking To Buy A Car Takes Wonderfully Wholesome Twist

It ain't all irrational, choosing beggars out there, folks! Every now and again, we'll stumble across a couple humans managing to navigate the ins and outs of polite conversation, without giving themselves over to fits of cheap disagreeableness. 

wholesome conversation viral texting mom win - 7704069
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Angry Pregnant Woman Loses It When She Fails To Scam Artist Out Of Painting For Free

This angry pregnant woman melted down into a puddle of unwarranted rage, when she learned that pretty paintings from artists trying to make a living, AREN'T FREE. Who'duh thunk it. She tries and fails to get a rise out of the artist, with petty texts that serve as personal attacks on the artist's skills. I wonder if she's busy painting that picture she wanted so bad, herself, instead! Good luck...

cringe freakout parenting Meltdown ridiculous pregnant texting choosing beggar - 7600901
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Aggressively Impatient KitchenAid Buyer Gets A Slice Of Justice After Sending Rude Messages

When the choosing beggar meets your sanely delayed text responses with a blatant and blind disregard for all the sh*t you have going on in your life....let them eat CAKE. This is pure and sweet-tasting justice. Warms the heart really. 

cringe ridiculous food texting cheap funny - 7596037
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Girl Photoshop Trolls Wrong Number Text From Scientologist

When a random scientologist reaches out to you, with a wrong number, it is your duty to take advantage of that with some kind of devious trolling. In this case, the silly photoshop trolling gives way to a rather ridiculous, ALL CAPS, meeting invitation. Definitely surprised over that outcome. 

scientology wrong number trolling photoshop texting funny - 7596549
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Monosyllabic Mouthbreather Gets Called Out For Being A Crude Choosing Beggar

This seller encountered a rowdy, rude-mannered choosing beggar out in the wild, and seized the moment, to call them out for their selfish stupidity. The ensuing conversation has a little bit of a fail and win, mixed in, and we are all about it. 

choosing beggar trying to buy a laptop for half the price
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Horrible Dog Trainer Gets Caught Up In His Sickening BS Scam When Beautiful Dog Goes Missing

Hunter Nelson is the villain in this stomach-turning tale, centered on the disappearance and potential passing of a beautiful dog named, Ollie, who never had a say in the matter. What happened here, and the shadow tactics at play to hide from the truth, is humanity at its very worst. The texts from the "dog trainer" show every sign of one twisted scam. 

terrible dogs evil dog trainer scam texting animals - 7501061
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Conversation With Choosing Beggar Goes From Annoying To Scary Real Quick

This has to be someone trolling. Please, by the grace of all that is good, let this be someone trolling. If not, the woman selling the bike did the right thing. People like this should be reported to the police. I honestly don't know what that choosing beggar was thinking - how dim can you be? She really thought that would work? 

choosing beggar goes from annoying to scary
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Choosing Beggar Lowballs Guy And Ridiculous Trolling Ensues

The best way to deal with those lowballing choosy beggars is to waste their time as much as you can, before they realize what's going on. That, that right there is priceless. So. Behold, all that in action right here. Good job to the seller for putting his whole heart into his trolling, if it's the only way we can get back at choosing beggars, I support it wholeheartedly. Troll away my generous friends. 

choosing beggar gets trolled
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Women Text Their Crushes About Valentine's Day Dates And Tweet Their Resulting Screenshots

Lust is alive and well in these text messages between interested women and willing men, in regards to Valentine's Day dates. Twitter User, @Oloni, kickstarted a Valentine's Day challenge for women to text their crushes about having had a crush on them for some time; and to share the results in a screenshot on Twitter, from there! The results we've seen are particularly successful. They'll either give you hope, or make you feel that much more content in your forever alone life. 

conversation relationships ridiculous texting funny holidays dating Valentines day - 7736837
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14 Cringe-Packed Texting Fails To Make You Feel Better About Your Darkest Hour

The standard, "oops I didn't mean to" isn't going to begin to cover these anger-inspired moments of impulsiveness. 

FAIL cringe Awkward ridiculous texting funny - 7399173
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Upset Jolly Rancher Customer Encounters Sweet Enough Customer Service To Give You A Toothache

Sweet, could be a stretch here, but the point is that this customer service rep. stepped up in a helpful way, when they encountered a dissatisfied customer, who didn't get that good 'ol watermelon rancher they were looking for. And helpfulness is a whole different kind of sweet. Good on them. 

customer service customers jolly rancher awesome conversation texting win - 7685381
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13 Cringey Neckbeards Who Mask Rudeness Behind Bloated Vocab Banks

We have here a finely assembled lot of cringelords who fancy themselves modern gents, with deep pockets filled with unnecessarily long words; and beneath all that, wild insecurities and genuine rudeness. Just cause you write something out in a way that sounds pretty, doesn't mean you're off the hook, for lashing out seconds later with a fiery round of profanity-laced verbal assault. Of this lot, I think that Phil's the MVP. "Is that clear?" 

wtf cringe Awkward conversation neckbeards ridiculous texting funny - 7683077
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