I'm not going to say who it is... and you probably wouldn't know who it is anyway, but I managed to sort of do this with a musician, haha. It all started out with me just being a huge fan (I expressed my love back when he was a nobody, and from then on, I was just known as his favorite fan), and then after meeting him at one of his shows, to accidentally coming across him at another, we eventually started talking a bit. I oftentimes forget who he is and no longer even view him as being even moderately 'famous,' and I just picture him as an average joe who just happens to make some of my favorite music on the side!
I didn't really get my charm across the first few times that I hung out with him (it's a bit hard to fully get to know someone at a club when alcohol is involved...), but it helped me get my foot through the door and move onto texting/phoning. We live in different states, and it's definitely just a playful little relationship that we have at the moment (ie, we're not like... being serious or dating or anything of that sort @@), but I've already got the okay to come visit him/stay at his place whenever I want! Let's just say that I'm planning a trip verrrrryyyy soon. ;)