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

25 Painfully Awkward Moments From Your Dating History

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Entry by burritomouth

25 Painfully Awkward Moments From Your Dating History

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Entry by burritomouth

25 Painfully Awkward Moments From Your Dating History

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Entry by YepThar

25 Painfully Awkward Moments From Your Dating History

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Entry by LilySprite

25 Painfully Awkward Moments From Your Dating History

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25 Painfully Awkward Moments From Your Dating History

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Entry by JadeCampbell

25 Painfully Awkward Moments From Your Dating History

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Entry by LilySprite

25 Painfully Awkward Moments From Your Dating History

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Entry by Chan Teik Onn

25 Painfully Awkward Moments From Your Dating History

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Entry by Buttersnix

25 Painfully Awkward Moments From Your Dating History

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Entry by Chan Teik Onn

25 Painfully Awkward Moments From Your Dating History

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Entry by PollyDarton

25 Painfully Awkward Moments From Your Dating History

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Entry by ChevySpoons

25 Painfully Awkward Moments From Your Dating History

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Entry by Wyrmologist

25 Painfully Awkward Moments From Your Dating History

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Entry by ERRiley

25 Painfully Awkward Moments From Your Dating History

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Entry by CornishPlasty

25 Painfully Awkward Moments From Your Dating History

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Entry by boffredi

25 Painfully Awkward Moments From Your Dating History

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Entry by masta_X

25 Painfully Awkward Moments From Your Dating History

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Entry by YepThar

25 Painfully Awkward Moments From Your Dating History

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Entry by LilySprite

25 Painfully Awkward Moments From Your Dating History

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Entry by munagam07

25 Painfully Awkward Moments From Your Dating History

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Entry by TaiGin

25 Painfully Awkward Moments From Your Dating History

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Entry by burritomouth

25 Painfully Awkward Moments From Your Dating History

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Entry by Scott Laffey

25 Painfully Awkward Moments From Your Dating History

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And the winner is ...

Congrats, jimclass. You win money.

25 Painfully Awkward Moments From Your Dating History

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