I'm interested in dating the brother of arguably the biggest celebrity in the world.
Any ideas on how to go about this without seeming like a climber? I am a big fan of the celebrity in question, but that has nothing to do with my feelings for her brother. He's a really great person from what I can tell, and I like him a lot.

How do I convince him of this? Apparently he has dated freaks in the past who are just interested in him because he's related to this person.
And how do I approach him in the first place?

jolie?

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That's the whole trouble. You can't ever find a place that's nice and peaceful, because there isn't any. You may think there is, but once you get there, when you're not looking, somebody'll sneak up and write "Fuck you" right under your nose.” - J. D. Salinger

a spiritual being having a human experience

gross, no.
it's madonna. i guess there's no harm in revealing that.

how the crap do you go about even meeting madonnas brother??

Um, you mean you don't know him personally already? I wouldn't try it.