How to make him fall for you? Let him know or let him guess?

I have a crush on my drama-cl-mate and I don't want to screw it all up. I've screwed so many things up by doing so stupid things I didn't even realize I was doing, or maybe because I've always tried too hard. I truly want it to work this time but I'm facing a small dilemma. Should I let him know subtly that I'm interested in him through my actions, words, tones.. Or should I "play the game" by trying to make him trust me as a true friend, confide in me, so that gradually he might develop a stronger feeling towards me?? I don't want to fail this because I can actually imagine us having a long term relationship, something I was never fond of. I guess I have grown to the point when a long term commitment sounds rather like a desired change rather than a plain fear, and this is the one I want to make the change with.