I've met a few famous people, but never really got to speak with them much
On spring break in 86 or 87 I ran into Pierce Brosnan at the San Diego Zoo. He was there with his family and was talking to my buddy and I for a minute before we realized who he was.
My wife's uncle was good friends with Joe Pepitone of the Yankees and back in the 90's he got us into a few of the player dinners for the Old Timers game where I got to meet a lot of retired ballplayers; even Dimaggio and Rizzuto. One time I sat next to Mike Torrez who was mostly famous for Bucky Dent hitting a home run off of him. Super, super nice guy. I met a lot of famous players, but most seemed annoyed they had to meet and greet anyone.
When my cousin got married I got to briefly meet Red Auerbach and KC Jones. Apparently the bride's father was a big shot with the Celtics. They didn't stay long, but as Celtics fans it was nice surprise for my dad and I.
Almost played golf with Tom Lehman once at my father-in-laws club. The place was nearly empty and the starter was going to pair us up with him but he asked if he could go off ahead to play/practice alone promising not to hold us up. Never seen anyone hit a drive so far at that #1 hole and we barely saw him again. He was at some of the Easter brunches and Thanksgiving dinners I went to at the club as well and at a Masters party. Honestly glad I didn't play with him as he never seemed to be a very friendly guy.