Before you take any of the advice that you get here, I would make entirely sure that this boy actually does like you in return. If he doesn't have the feelings for you that he think he does, everything you do in pursuit of this kid will be for nothing. That being said, the best advice I can give is to take the whole "first step" thing upon yourself. In the modern world, girls are very critical of guys and he is probably just afraid of getting turned down or made fun of for the same action... If you still want it to be a "classic" get-together, make sure that there is NO WAY he is not aware of your feelings for him. Make it so he KNOWS you'll say yes and the world is yours.
Good luck!
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Quote for Truth, betches... Out.