Our expert says:
It actually has nothing at all to do with the way you look, in the sense that what's cool today will be very uncool next week, and what was so cool 20 years ago, looks bizarre these days.
I agree with Delene that something like wit is more timelessly cool --- their are good Roman jokes that are still funny.
Had to smile at Dude's definition ! That's cool. Don't sit on any Holly
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