Dating Fails

Awkward

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Guy Proposes to Girlfriend on Kiss Cam, Gets Interrupted at the Worst Time Possible

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Girl Live-Tweets Her Suspenseful Attempt at Hooking Up With Uber Driver

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Ten guys that are forever banished to the status of being in the friendzone with their crushes.

10 Dudes Forever Banished to the Blue-Ball Confines of Friendzone Hell

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Woman who is trying to break up with a guy peacefully, ends up getting rushed by a freakout texting rant.

Woman Trying to Let Guy Down Easy Gets Stormed By Crazy Text Rant

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Traumatized daughter is somehow in her mom's group chat.

Traumatized Daughter Was Caught In Her Mom's Cringeworthy Sexting Crossfire

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Ten hilarious tinder conversations full of cringeworthy funniness.

10 Glorious Awkward Tinder Moments That Deserve Places in Hall of Cringe Fame

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cringeworthy tinder conversations

15 Inescapably Cringeworthy Tinder Conversation Moments

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cringe text conversations

Guy Texts Ex Trying to Set Up Threesome for Girlfriend, Girlfriend Realizes It and Pulls Brutal Power Move

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This Date Got Awkward

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Via See Mike Draw

It's an Awkward Age for Everyone

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MILFs share the cringiest and saddest stories of advances they've received from younger men.

31 MILFs Share Stories of Saddest and Cringiest Advances They've Received From Younger Men

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Guy gets rejected in terribly brutal manner, and goes viral after the conversation is shared on Twitter.

Guy Goes Viral After Getting Rejected In Most Savage Way Possible

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When You Get Caught Staring at Your Crush

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Via Awesome_Bro_Hug

This Is How We Flirt

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Via 321hammer
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Girl live-tweets extremely entertaining and awkward date with old man she meets through OkCupid Dating Service.

Girl Live Tweets Cringe-Soaked Date With Old Man She Met On OkCupid

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the saddest loneliest cringe photos you'll ever experience while sitting crying on the floor

12 Shameless Moments Of Sad Cringe To Make You Feel Better About Your Worst Days

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