Awkward

Thirsty Dude's Shameless Attempts at Getting Nudes From Girl Go About as Well as You'd Expect

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Kid Asks Mom Too Many Questions About Her Divorce, Learns They Played Instrumental Role In Separation

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

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These Cringe-Inducing Conversations Are Guaranteed to Leave Your Skin Crawling After Reading Them

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Straight White Boys Texting is a Thing of Beauty

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19 Cringeworthy Pics From People You Never Want To Meet

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

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Crazy Ex-Girlfriend Tries and FAILs Miserably to Ruin Newly Married Man's Relationship

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Awkward Picture Shows Donald Trump's Tie Is Held Together by Scotch Tape

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J-Pop Star Meets One of Her Crazed Fans

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Kids Of Karens Describe Their Experiences

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20 Times The Pizza Delivery Guy Had to Deal With A Supreme Combo of Cringe and Stupidity From Customers

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Unsuccessful Handshake

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Pro League of Legends Player Goes in for a Hug From His Ex-Teammate, Gets Denied Hard

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Awkwardness? At QuakeCon? No Way!

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This Five Is Too Damn High!

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