Having the guy not shave hurts more, at least for me, after a fresh shave. At the very least be trimmed, because super-hairy is irritating and scratchy on my bare skin, heh
I dunno, it depends a lot on whether or not I'm seeing someone. If I am, and we're at the pants-off stage or close to it, I usually shave the day before I see him, or the day of. With my last guy, that was once a week. Otherwise... once every week or two, since no one is gonna be seeing it anyways.
oh, I don't shave completely either... I leave a path near the top so it at least looks like I've hit puberty