In the Year 2000...
The entire notion of someone meeting their boss after they've started their job is still a little Bizarro to me. Though I'm a mere 31, even when I was in University, TEH INTARWEB was fresh, and the concept of telecommuting was still, well, a concept - not unlike the Segway ("sure, I understand how it works, but is anyone really going to do it?").
Obviously things are different now. I enjoyed this description by The Sports Guy's Intern of meeting his boss for the first time, though he's "known" him for 7+ years:
I made eye contact, started walking away, turned around and made eye contact again, then decided to take a quick lap around the place just to see if I can find a closer match. After a lap around the bar, no luck. Here went nothing:
"Excuse me, is your name Bill?"
"I work for you."
"HEY! How's it going?"
"Hey, not bad! Sorry about giving you the staredown before!"
"No problem, I just thought you were gay."
So there you go. After seven years, at long last, a first impression.
The Sports Guy. Heh.