You've just got to jump in the water on this one. It's never easy to make yourself emotionally vulnerable like that, but if you never try you'll never know what it could've been.

So here's the key line for you to say:

"Do you ever think of me as more than a friend?"

Wait to ask this until you're both alone, having a nice quiet time together with no distractions (like other friends, family, loud music, etc.).

This line is perfect because it's:

A.) Honest
B.) Implying that you have thought that way, without having to actually say it
C.) An easy out for him

If he's really thought about you, it will be a "yes", and you can go from there and discuss "Well maybe we should try dating, what do you think?".

If he's never thought about it, but isn't turned off by the idea, then he might say "No", but could come back later and change his mind. This plants the seed in his head to "start lookin'".

If he's really not interested, he'll be able to tell you that he really only ever wants to be friends and that's it. And if that's the case, with this line, you shouldn't feel too awkward or terrible. He's being honest, and you should focus your swooning eyes on someone more worthy who will really notice you!
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How about if you go up to him and say, "A secret admirer wants to ask you if you're dating anyone, and if you'd be open to the idea of a date?"... and then see how he reacts.

If he's not already attached, and if he seems cool and casual, or even excited, by the idea of meeting someone new, then pop him with the statement, "Well, it's me!"

If he's worth his salt as a guy, he'll see the humour in that, and it means you'll be starting your relation with a laugh!
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I think you should ask her to go to dinner or lunch and try to ask her what she thinks about you and try to tell what you think of her in a fascinate manner to her.
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