Awkward

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Oooooo This is Awkward...

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

Ten guys that are forever banished to the status of being in the friendzone with their crushes.

10 Dudes Forever Banished to the Blue-Ball Confines of Friendzone Hell

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Too Many People Lose at This Point in the Game

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Could You, Uhhhh, Do That Somewhere Else?

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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Hit That One On The Nose

Date flips out when she realizes that she has to pay for her own food | Hey, wann go out tonight? After did last time expect go out with again? Wow have done??9 made pay my own food and drink while paid only yours wtf

Date Has To Pay For Her Own Food, Flips Out

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

cringey awkward texts from exes

10 Awkward Texts From Exes That Should've Stayed In The Drafts Folder

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Awwwwkward

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This Walk Isn't for the Faint of Heart

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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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...Thanks a Lot

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Maximum Hover-Hand