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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Womp Womp Wooooomp...

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Things Just Went From Dramatic to Cringe-Worthy in This Breakup

Via Coaz

Will You Be Mine, Savior?

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Created by Hellbilleh

Oh Nien He Didn't!

Awkward blonde hitler - 5797437952
Created by Unknown

The Founder of MegaUpload is Looking for Love

Via KimDotcom
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Mailman Fails Terribly, Leaves Package In the Worst Possible Place, But Pulls Through With Hilarious Note

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Phrasing is Important

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Neil deGrasse Tyson answers question on Twitter about taking shirt off, but it's very awkward taken out of context.

Neil deGrasse Tyson Has Hilarious Tweet Mishap, Reveals He Struggles With His Pants

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Happy Date and a Proud Dad

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Via Bro My God

Someone Doesn't Approve?

pregnancy Awkward texting - 4820890368
Created by Kaschews

Another Reason to Never Friend Your Grandparents on Facebook

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That Feeling When You Know You've Lost Her

Via Brown Cardigan

How to Weasel Your Way Up the Corporate Ladder

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Aaaaaaaand BLOCKED

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Via Acid Cow

Millenial Youtube Star Shane Dawson With Some... Questionable Youtube Commentary

twitter Awkward - 8426047232
Via Shanedawson
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