Torn Between Risk and Safety

So here's how it is: either I risk it all - his friendship and my current circle of friends - on the slim chance that he might like me back, or I play it safe and remain silent.

But god, it's so hard when people are always asking me, "Are you going out with him?" and I'm forced to hold back the despairing sigh and reply "No, we're just friends."

It's so hard when the more intuitive of those people say, "But you wish you were" and I'm forced to either tell the truth and nod, or lie to their face - and to myself.

And god, it freaking sucks when that person then says "You know, I always seem to be the matchmaking fairy godmother. Okay, here's what you do..." and gives me some advice. And why does it suck? Because even though their advice is absolutely wonderful, even though it's completely perfect, it's flawed in one major way: I'm not bold enough to do half of what they say. People always tell me, "Well, just tell him" - can't, I'm a wimp and I don't want to ruin our friendship. They say, "Okay then, see if he'll see a movie/study/go shopping/etc. with you" - again, I can't, because again, I'm a wimp, and I doubt he'd want to do anything with me anyways. Usually their third bit of advice either involves them telling him for me, or some complex and completely unrealistic situation in which he somehow miraculously realizes he loves me to, and blah blah blah - basically your standard Disney story.

One of the only really practical bits of advice I've heard was something a friend brought up yesterday - or rather, two ideas she had.

1 - "Well, see if he'll go to the Winter Ball with you and some of your friends." My only complaint against this is that I'd have to ask, and I'd inevitably screw it up somehow, and my only real argument against it is that most of my friends already have boyfriends...so it would be kind of awkward.

2 - "OH! He should go see Twilight with us!" Again, I'm not about to ask; last time we talked about it, he seemed really reluctant, so I doubt he'd want to go with my friend and I. Unfortunately...

So I'm going to go on being a wimp and saying nothing, playing it safe, even though he keeps telling me that the greatest risk brings the greatest reward (yeah, he actually said that today, although it was about offering my opinion on a history worksheet we were doing), and looking for the for dummies book on love and relationships.