Dating Fails

Awkward

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The Sexual Tension Is Stifling As Couples Describe the First and Last Time They Had Sex

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Collection of awkward times people blurted out cringeworthy things to their crushes.

43 Terribly Embarrassed People Share the Most Cringeworthy Things They've Ever Said to Their Crushes

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

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cringey comment threads and cringe-worthy DMs

14 Cringe-Packed Texting Fails To Make You Feel Better About Your Darkest Hour

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Probably Happens More Often Than You Think

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By Unknown
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Turning For Romance

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Via See Bang Now
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Good Guy Benny

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By anselmbe
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FAIL cringe Awkward relationships dating - 80276993

Chinese Couple Floods the Street with Awkwardness as a Dude Begs for Second Chance

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Bill Murray Needs to Work On Technique

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So. This is Awkward.

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Via There are Clouds in the Sky
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Awwwwkward

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By Unknown
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Well. This is Awkward.

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By Unknown
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Girl Live-Tweets Stranger's Catastrophic Date Next to Her, and It's Mortifying

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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

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Pre-Date Strategy Planning

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Guy gets friendzoned again during texting conversation and has a terrible cringe reaction to it.

Dude Gets Friendzoned (Again) and Has Shamefully Cringe-Packed Reaction

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