I seem to be nostaglic as far as pop-culture. I listen to 60s-70s-80s-90s music...and watch shows like Seinfeld, Frasier, Married With Children, Full House, the original 90210, X-Files, Cheers, Who's The Boss, 90s Simpsons, and so on. I dress like someone from the 90s (kind of like Niles in Frasier) and like women that dress like Roz or Elaine (Business woman look.) I seem to have better conversations when I go on dates with 30 or 40 somethings than with women my own age.
The only thing I can talk to men my own age about is common friends, sports, or women. With women, I just listen to what they have to say about themselves.
I get the impression that if you gave me my same exact life, and made me this age in 1995ish, that I'd be "hip" back then.