It's already kind of weird to regularly get comments from or interact with geek 'celebrities' both big and small, (saurik, Alan Kay, etc.). Sometimes it bleeds over into the real world where I mention so and so said something to me about whatever topic we're on, and then I have to explain that it was a comment on a badly-styled website and try not to out myself at the same time.
But even weirder is how likely it is that many people that I used to know from various internet places (Massassi Temple, Something Awful, TTLG, IRC channels) are also active here. Not to mention that I know for sure that some techies I know are on here too.
I think what makes it feel weird is that HN is both relatively well-known and small at the same time. The places I frequented growing up were obscure enough that I wouldn't know anyone from 'somewhere else', whereas a site like Reddit is so pervasive that any comment I post gets lost in the noise (probably half of the thirty-something-and-under crowd I know is on Reddit).
EDIT: I think the weirdest 'celebrity' encounter I had was the time I had dinner guy who created CSS Zen Garden. That website was one of the resources that got me started on my web developer career.