Couple...uncomfortable ones.

I used to play soccer on a team with Martin Gore of Depeche Mode. We were at the bar who sponsored our team and I was playing doubles pool with a friend against Martin and someone else from the team probably. A song came on and I was like "Oh man I haven't heard Yaz in years" but realized after Martin kind of gave me a look like I was an idiot that it was Vince Clark era Depeche Mode. OOF!

Not unpleasant so much as awkward. When I was a checker at Vons in Santa Barbara Tom Villard (prolific character actor in the 80s-90s, something like 30 films in 15 years) came through my line. He could tell by the way I was looking at him that I recognized him but could not recall his name. At least that's what I got out of the look. We both kind of smiled awkwardly. It was funny.

The only truly unpleasant one: Anderson, Bruford, Wakeman, & Howe show at the Greek Theatre, 1989. I met some dude, who invited me back to his place in Woodland Hills or some other Valley 'hood, probably to drug and sex me, told me that if we waited at a certain spot we'd meet the band as they left. So we go there and wait. I was wearing an "In the Court of the Crimson King" t-shirt and Bill Bruford saw it and said "Oh Christ." I imagine due to my age (I was 17). Let's see your "In the Court of the Crimson King" t-shirt, cocksocket!