Search Results: get her without risk

This year I joined the drama club. During it, although it's over now, I got to talking to a friend's brother, him a couple years older than me, and developed feelings for him. With my shyness, two out of three times when I wanted to talk to him, I didn't even open my mouth, much less actually make words come out. There were many opportunities I missed, so I'm afraid I gave off the vibe that I wasn't interested in even being friends. He seems to be quite shy himself, which makes it worse.

Now, I haven't talked to him in awhile because the play is done, but we're both joining a club that is just starting for the year. I figure this will give me more opportunities to talk to him whereas I hadn't had any since the play finished.

I don't know if I should ask him out at all, if it would be a bad idea because of him being my friend's brother or maybe because of the age difference. I don't know him all that well and have no idea what he thinks of me. On one hand, I'd like to get to know him better without any pressure, but at the same time, I'd like him to know that I think of him romantically.

What should I do in this situation?

If I ask him out, and on the off chance he says yes, then there's already potentially expectations when we don't even know each other that well.

If I just ask him if he wants to hang out some time instead of specifying it as a date, pressure's off, but then I risk him not realizing my intentions.

I could always let it play out come what may as we get more chances to talk with the club, but I figure the longer I wait, the harder it'll be to actually ask him out. I've been known to push things like this off and then chicken out.