- show him a completely novel world that's a bit zany
- pick up on the little things he does, as he speaks less, does a whole lot more, and be original in your response to show that you 'got it' (by catering to his particulars, that are unique to him...like remember something he mentioned offhand he really liked)
- don't back away from going toe-to-toe in your views, and listen openly to his
- appreciate the oddball sarcasm and throw a few back
- you may not know it, but once he, in his mind, has gotten signs that you guys can have serious potential....he's off dreaming ("planning") of how you guys will be down the road, years later.....if he lets some of these visions slip, almost casually (to test how it's received), don't shy away from it, if you're ready and willing to go there. If he sees you retreating, he'll be once bitten, twice shy
- be spontaneous, adventurous...he's secretly wanting you to drag him out of his shell a bit