I worked in the music industry for years, including owning a music venue, so I have met and worked with/for tons of famous musicians - everyone from the Three Tenors to Prince to Counting Crows to Leo Kottke to Leann Rimes to…well. Years of that, plus knowing other people in peripheral industries and being invited to good parties means I’ve also met Malcolm Gladwell, Stephen King, Jon Stewart, others.
I did end up dating a few musicians, mostly against my better judgment.   But, while none were very serious, I do have a couple of Platinum Record/Top 10/Grammy/Juno notches on my belt.  
  I also had a long-term relationship with a very famous Canadian painter, although I don’t think you could call him a celebrity.  That word seems to be reserved for actors, musicians, socialites, and reality show stars.  :rolleyes:
Both my father and stepfather are politically oriented, and have organized and thrown many rallies, so I’ve met several Senators and Reps, Paul Simon being by far the most gracious, down-to-earth, and, in my opinion, brilliant. Also, John Malkovich’s parents and my grandparents were very close, and one of Jerry Sloan’s daughters is one of my best friends.
I dated a doper who is considered a big deal by many, and through him I met Dave Foley, Lou Diamond Phillips, Seann William Scott…I don’t know who all. And went to some premiers where I rubbed shoulders with the likes of Patrick Swayze and Drew Barrymore. He’s fairly easy to find if you search here, and a damn great guy.
My current boyfriend is a very recognizable local celebrity. While he probably wouldn’t be known nationally outside of certain circles, he’s recognized almost invariably in our major city.
I too often find famous people (I’m looking at you, actors and musicians) to be incredibly damaged, but it’s really effin’ cool to talk to someone who is immensely talented, but also incredibly smart, gracious, personable and (IMHO) deserving of all the kudos and perks they receive.