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Yeah, the initial contact is usually the hardest part I find.
I had a bit of the same problem with my girlfriend. She was a lot hotter than any of the girls I had dated recently and I wasn't quite sure if she liked me, so I was especially nervous.
I managed to make my move the geekiest way possible... Showing her how to play Halo. She had never really played any games like that before, so she was a bit lost on everything and couldn't even really get the whole movement thing down. So, after a whole bunch laughing and telling her what to do, I pulled the whole "Guide her hands" move, and it worked. I did it as kind of a half joke, half "break the initial contact". From there on, smooth sailing.
That being said, to make the initial contact, try to find a reason to touch her hand that goes along with the conversation you're having. Go on a date a bit less passive than a movie. While you're talking to her, you'll find it easier to gauge how much she likes you, which will help you decide when to make your "move"
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