Ask him if he's seen a certain film or band, and then if he'd like to go along with you. If you can't afford to go anywhere, ask him if he knows something about computers - make up a prob - then ask if he could come round and help you. You'll know by his attitude whether he's interested or not. If he agrees to something on the above lines, don't be too pushy. Thank him afterwards and say you'd like to do it again sometime/maybe he could show you how to fix...whatever. His reaction'll tell you if things are going well or not, without having to feel stupid or rejected. Good luck!