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“I decided to see if I could fit my entire hand into my vagina.”

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“I was in my grandmother’s bathroom. My girlfriend at the time was uncontrollably sexting me, and she sent me a video of herself that I knew was meant to be watched in private…”

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When we got back up on the bed, I was lying on my stomach and Jake was on top of me, inside me, as we enjoyed our drunken sex.

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How many of these embarrassing, late-90s mistakes did you make?

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Sure, putting yourself out there or taking a huge risk can result in a major face-palm moment, but I think not even trying to be different, to experience new things, or to open yourself up to possible humiliation — well, that just seems so much worse than actually being embarrassed for a few seconds.