Most Helpful Guy
why not go up to him and start conversaton, take advantage of his shyness...you know its not always the guy taht has to do everything. When girls come up to me, its extremely attractive, it shows confidence and its really attractive. Just like you girls like, we like the same kind of thing, its 2011, the guy doesn't have to be the first every time...
if you start to make conversation he'll feel less weird or awkward around you, make him feel comfortable, do things together, socially, in groups. That way there's no awkward silence or feeling pressured to impress you.
i wouldn't suggest a movie or anything, the first couple of dates should be getting to know one another better...a movie is just silent and sitting next to one another can feel awkward esp if you have never done it before...just do something fun and social and interactive...go karts, putt putt, water park, anything where you two can talk but still have fun and joke.
take things slow! hope this helps, gl