Do you think this will work?

Well, this morning I curled my hair and planned on asking this guy who I think likes me to go on a walk. And then walk past this local bowling alley and be like, hey let's go bowling! Except that now it's raining. I want to tell him somehow that I like him too, but subtly. Should I ask him if he's planning anything with his girlfriend next monday (Vday) to get him to tell me he doesn't have one and ask me if I have a boyfriend? I just don't know how to get the ball rolling. Please help me!