Dating Fails
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Awkward

people share their worst date stories

17 People Share The Absolute Weirdest Dates They've Been On

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cringe Awkward prom Video dating - 70344193

Things Get Awkward Fast When This Guy Attempts an Elaborate Promposal

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Girl gets creepy texts from her ex-boyfriend who thinks he saw her current boyfriend out in public.

Girl Gets Creepy Texts From Thirsty Ex-Boyfriend and Instant Cringe Ensues

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funny dating fails

Dude Texts Wrong Number Thinking It's a Girl, Finds Out It's a Guy, Proceeds With Lusty Persistence Anyways

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People share stories of the cringiest things they did to try and get their crushes to like them back.

53 People Share the Cringiest Things They've Done to Try and Get Their Crushes to Like Them Back

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dudes trying way to hard to get the girl

20 Dudes Who Are Trying Way Too Hard

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Awkward prank sexy times funny Video - 54133761

What Happens if You Ask a Stranger for a 3some?

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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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Aggressive texter bombards guy's phones with paragraphs | Oh shoot. So sorry did not mean send s little embarrassing My old phone didn't allow send videos and since just got this one on Thursday still trying see can do and dunno pressed scrolling through my gallery but total accident and now really embarrassed so 's best don't talk anymore ?

Woman Bombards Man's Phone With Storm Of Texts

Yikes.
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Well This is Awkward

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Mike Rowe Knows Awkward Sex When He Sees It

that's a tough shaft to work
Via m0rris0n_hotel
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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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Cringeworthy stories of the worst sex that people have ever had will make you shudder terribly. | Preacher's daughter kept telling Hurt pagan boy over and over again while she laid there and refused do anything.

These 40 NSFW Cringeworthy Stories of the Worst Sex People Have Had Will Make You Shudder Uncontrollably

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sex-ed class cringe questions

People Share the Most Cringe-Worthy and Hilarious Questions That Were Asked During Their Sex-Ed Classes

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Marry Me

pickup lines, awkward, so close, nervous
Via Reddit
20 stories from people about moments in their lives when nothing good went their way.

Feel Better About Your Monday With These 20 Painful FML Stories

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