Awkward

Girl finds most coldhearted way to break up with four guys all at once.

Coldhearted Chick Breaks Up With 4 Guys At Once In Most Savage Way Possible

Guy tries to make another girl jealous through texting conversation by pretending that he has a girlfriend and it backfires.

Idiot Pretends to Have Girlfriend to Make Another Chick Jealous and It Backfires Horribly

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

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This is Awkward...

cringe dating

Coffee Shop Creeper Texts Barely Legal Barista and It's an Awkward Exchange

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

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

People share the silliest reasons they stopped having sex halfway through.

51 People Share the Silliest Reasons They Stopped In the Middle of Having Sex

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This Guy Wants Jennifer Lawrence to Go to His Senior Formal With Him, so He Wrote Her a Creepy Song

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

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Every Damn Time

Cringeworthy couple that needs to get off of social media.

20 Cringeworthy Couples Who Need to Get Off Social Media

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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STAHP

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This Guy Makes PDAs Way More Awkward

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