Dating Fails

Awkward

Girl tweets her boyfriend's terribly misspelled text message thread and it goes viral instantly.

Girl Tweets Her Boyfriend's Hilariously Misspelled Text Message Thread and It Goes Viral Instantly

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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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It's an Awkward Age for Everyone

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By Unknown

Fail fail fail fail and fail

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Via LucLucian

This Date Got Awkward

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Via See Mike Draw
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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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Well That's Going To Make Any One-on-One Meetings Awkward and Hard(er)

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Via The Sun
dudes trying way to hard to get the girl

20 Dudes Who Are Trying Way Too Hard

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Let the Gentle Caress of a Stranger's Hand Make Your Escalator Ride Uncomfortable as Hell

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Awkward Date Moment

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By Ivanna Cumalot
couples getting divorced

14 Times Married Couples Failed To Get Divorces Due To Unforeseen Circumstances

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

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True Romance Under a Full Moon

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Via Laughing Squid

Jimmy and His "Friend" Are Wicked Awkward

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Via Dogjpeg
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Blind Dates Don't Have to Be Agreed Upon

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cringe text conversations

Guy Texts Ex Trying to Set Up Threesome for Girlfriend, Girlfriend Realizes It and Pulls Brutal Power Move

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