25 Painfully Awkward Moments From Your Dating History

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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:

Entry by YepThar

CRACKEDc Date took me to a fast food place. He told me I was allowed to order from the dollar menu only. He ordered a $6 burger. I turned around and l

Entry by jimclass

At my sister's wedding, I hooked up with one of the bridesmaids, who had been her college roommate. thank you for being my BRIDESMAID Icouldn't say I
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