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OK, I'll be honest: I think it's a little creepy. Not majorly creepy-- as long as you're not picking your date up from junior varsity mathletes, it's not majorly creepy. But a little. When I see couples like that, I always wonder: his midlife crisis or her daddy issues?
That said, women mature much faster than men, and it is only natural that a girl of 20 might be fairly sick of dating the yutzes in her age cohort, and want to date upward. And I will certainly admit that, at 35, I still check out 20 year olds all the time, and-- were I not involved-- I might seriously consider my options did a 20something hottie put the moves on me. Still, I don't know if I could.
My general rule is that once the age difference passes the double-digit mark, you're starting to tread into weird area. My hard limit is usually set at 13 years: if a girl's a whole bar mitzvah age kid ahead or behind me in age, it's just too much. I think 15+ years, there is very little chance of it not being at least a little weird.
But again, on the spectrum of potentially creepy things, even a 20-year age difference is fairly mild, unless the difference ends out with someone being a teenager....
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Dull sublunary lovers love,
Whose soul is sense, cannot admit
Absence, because it doth remove
That thing which elemented it.
(From "A Valediction: Forbidding Mourning" by John Donne)
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