The funniest encounter I've had: Riding along in town with a friend on my Xtra's snapdeck. She's snapping shots with her camera and we're making a good time of it. I had checked my rear a few minutes ago and noticed a rider - a roadie - headed up along us in the bike lane. (It's a 35mph road with plenty of traffic, so we use the bike lane.)
Relevant aside: I volunteer with my school's bike team and will, with all luck, be riding with them come fall (cyclocross) and spring (road). I'd just been out a couple days before to help flag our collegiate race, hitched a ride with a couple of guys from the team.
And riding past me was one of said guys in full kit. He glanced over, realized it was me, then just looked confused for a second before striking up conversation.