Dating Fails

Awkward

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James May of "Top Gear" in His Most Awkward Moment of Flirtation

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Cringeworthy couple that needs to get off of social media.

20 Cringeworthy Couples Who Need to Get Off Social Media

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It's Always Awkward Being The 3rd Wheel

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Created by Unknown
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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I Might Need To Move to Another Country

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Via ilovecharts
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bridezilla, wedding, wedding drama, fail, ridiculous, trashy

Pathological Liar Bridezilla Tries To Get Married In A Month, Berates Maid Of Honor, Has Terrible Wedding

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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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EVERY.SINGLE.TIME

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Via ebaumsworld
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I Don't Know What To Do With My Eyes

awkward, dating, image, anxiety
Via Humans of New York
Entertaining Tinder profiles and conversations from particularly humorous individuals into modern dating game.

Fresh Collection of 5-Star Tinder Profiles We Fell In Love With

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Desperate Dude Doesn't Care That This Girl Is Only Into Chicks, He Needs a First Date

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You Will NEVER Live This Down

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Created by Unknown
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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Awkward - 45822465

Blind Dates Don't Have to Be Agreed Upon

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Awkward running love dating - 80064001

Running in the Shape of a Heart Is the Perfect Pickup Line to Start an Awkward Conversation

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I Sprayed My Heart Out to You!

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Created by Unknown