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Well... That Could Have Gone Better

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Wow, What a Deep Thinker

Screen capture of a dating fail exchange about how cold air doesn't make him shrink up.

Via Brown Cardigan

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Such a Shame

Funny exchange on Omegle in which the stranger indeed has boobs, but he is still a guy.

Created by anselmbe

That's the Best Message?

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Via Kitmhairi

Seems Reasonable to Me

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Via I Threw My Pie for You

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An Offer I Can Refuse...

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Created by Unknown

Some Wounds Run Deep

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Via Vausexual

Well, That's New

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Created by ryann.warlick

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Think of the Children

Dating fail of when you might be overthinking things just a bit.

Via Oh No She's Single

That's What Serious Relationship Means?

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Created by jenny01

Some People Just Can't Take "No"

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Via Grace ft. Hannah

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Sexiest Chat of All Time

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Real Smooth, Guy

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Your Fave What?!

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Via My Heart on the Floor

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Jimmy and His "Friend" Are Wicked Awkward

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Via Dogjpeg

Odds Are It Wasn't a Typo

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Via KiaMatthews

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