Most Helpful Guy
just go hangout with him, do something fun, eat good food, maybe dance a bit, play some games, then go home together and watch a nice movie or something, pour out the wine or whatever, see what transpires.
Most Helpful Girl
tell him whatever it is that you wanna do. I usually suggest going downtown to dinner and a bar.
I like to suggest public dates first just to make sure he isn't the lazy type whos only after me to "come over and chill"