What is Free Five?
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When in a relationship, both partners agree on five people (generally celebrities) that one would allow the other to mess around with if they were given the chance. Celebrities are the norm because the chances of actually meeting a celebrity and subsequently getting the chance to have sex with them is highly unlikely.
"Last night I met Justin Timberlake at a club and we fucked back at his hotel."
"Isn't your boyfriend going to flip out?"
"No way, it's cool. Justin's on my Free Five!"
See
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Eloquent Nerd-speak for "sucked" or "gay" (but not in an 1880s way).
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