Lurkette, thank you for this thread. I have a lot of thoughts about this subject, and I hope you don't mind if I indulge myself. By the way, congratulations on your awesome fan experience!
First of all, I think all humans, no matter how cynical or methodical, have an urge to connect to some "magic." We need that feeling of electricity in our lives, and celebrities are perfect for that. Realistically, John Lennon was just a white guy who played guitar, sang some songs, and wrote some songs. Millions of people can do that, right? What's the big deal? However, anyone who was ever around Lennon in person usually remarks on the electricity surrounding him. Magic. Charisma. Immortality. All of those things. Through some quirk of fate and karma, Lennon transcended all those other boring singer-songwriters and soared, and you couldn't NOT notice it in his presence. I believe that all celebrities share that same quality, and their irresistability lifts our lives in some way we can't explain.
Having said that, I've been blessed to know and spend time with some celebrities (music, acting, sports, etc.) and I've seen them as "normal" people. My relationships with them always causes me to re-think my "fan" attitude towards other celebrities, and I try to relate my experiences with my idols back to my relationships with other celebrities. Just like you, I want to ask them the one question that will cause them to remember me. I want to make such a cool impression on them that they will want to maintain correspondence with me. I want my own private tap-line into that magic.
What I have come to believe is that celebrities are more apt to remember your interaction with them if you ask them something that relates to them being a "normal" person. Trust me, whatever brilliant question you think you've conjured about their career or art, thousands of other people have beat you to the question, and they've probably settled back into giving rehearsed, meaningless answers. Ask them something that makes them snap out of monotony and actually makes them think.
My favorite question is, "What all did you get to do today?"
If you are lucky enough to get a follow-up, THEN ask that brilliant question about their career and art. You might actually get a sincere answer from that angle.
Now, after having typed all that psycho-nonsense, I have no doubt that if I found myself face to face with Sir Paul McCartney, I would be reduced to a useless, babbling idiot, and I would totally blow whatever miraculous chance I had.
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Living is easy with eyes closed.
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