25 Painfully Awkward Moments From Your Dating History

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Relationships are hard, and we all make dumb mistakes along the way. Misery loves company, so we asked our readers to tell us about their most awkward, embarrassing, and generally unfortunate romantic encounters.

The most painfully awkward is below, but first, the runners-up:

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Entry by sonoftime

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Entry by burritomouth

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Entry by burritomouth

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Entry by YepThar

Entry 22

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Entry by LilySprite

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Entry by JadeCampbell

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Entry by LilySprite

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Entry by Chan Teik Onn

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Entry by Buttersnix

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Entry by Chan Teik Onn

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Entry by PollyDarton

Entry 14

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Entry by ChevySpoons

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Entry by Wyrmologist

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Entry by ERRiley

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Entry by CornishPlasty

Entry 10

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Entry by boffredi

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Entry by masta_X

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Entry by YepThar

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Entry by LilySprite

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Entry by munagam07

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Entry by TaiGin

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Entry by burritomouth

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Entry by Scott Laffey

Entry 2

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And the winner is ...

Congrats, jimclass. You win money.

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