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I recently received an email from a completely overeducated blonde girl friend of mine, who boldly declared the following:
"Were this the sixties, I like to imagine you'd be fucking JFK.  And I, hopefully, would be banging Arthur Schlesinger."
Of course I love the sentiment, but I would totally not be fucking JFK, probably because Jessica Cutler would get to him first.

Also, I never date the hot guy that everyone else wants, mainly because I'm highly contrarian and the whole idea of everyone else wanting someone (or something) turns me off.   And, although I love gorgeous, smart men, I do not like to compete for them, because I am lazy and not particularly a fan of "rejection."  Thus, it's much more likely I would be fucking JFK's head speech writer, because that is how I roll.

Or, to use a modern day example:  Aaron Sorkin.

Although, actually, the man has lots of ladies now, so probably more like Aaron Sorkin in high school.  Mmmm ... yum.

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