Since everyone else seems to be doing it, I thought I'd give you all you non-hitchhikers a brief intro into the fantabulous world of Zaphod Beeblebrox. To do a full history would be downright impossible, but I can give you a few facts relevant to FH.
Zaphod's priorities are, in the following order:
1. Zaphod Beeblebrox
2. The coolness of Zaphod Beeblebrox
3. Getting Zaphod Beeblebrox drunk
4. Getting Zaphod Beeblebrox laid
5. Having a generally good time
This makes it sound like there isn't much in him, but nothing could be further from the truth. I think. Zaphod Beeblebrox in one of the smartest sentient beings in the entire galaxy.... At least, we think so. Zaphod's genius is (paraphrasing here) that you can't tell if he’s pretending not to know what’s going on, or if he really has no clue. For example, he can operate complicated ships with little or no training. But he might just be pushing random buttons. That's pretty much a metaphor for his entire life. If he wanted to, he could take over the universe (he almost did), but he'd just as soon have a drink.
As far as relationships go, Zaphod doesn't really do them. It isn't that Zaphod doesn't care about other people; he just cares about himself more. But he did care very much for a woman named Trillian. He did some very un-Zaphod like things for her, the most shocking of which was plan someone else into his life. We are given the sense that he didn't do the best job of it, but he did try. This is a shipper speaking, but his relationship with Trillian was one of the few things that he put effort into. She didn't factor into his plans, but he made a place for her anyway. He didn't give away that he was trying, because that's just not what he does.
This should give you a decent idea of what Zaphod looks for in a relationship. He may screw anything that walks, but it takes one hell of a woman to get him to settle down. Hence, the crush on Principal Conner. It’s not just my fangirlness that led me to write in the crush, though that of course factors in. It’s the fact that, canonically, there’s no other woman in the school Zaphod would give the time of day to.
As far as Zaphod in continuity, we don’t see him appear in the published books after Life, the Universe, and Everything. We hear that he and Trillian were together for a time (we actually hear that they had kids, but then reality is screwed with or something), and then we see that Trillian has left Zaphod and is quite bitter about the whole thing. So I’m playing Zaphod a year or two after the breakup. He’s as cool as ever, but probably missing Trillian a bit.
As far as Zaphod’s attitude towards life here at Fandom High...he’s operating on the assumption that the world is due for demolition, so it doesn’t much matter who runs the world, who’s eaten by the giant squid, and who passes class in between. When the Vogons come, he’s going to get happily fly away, and he heartily suggests you get in ship and do the same, because you aren’t catching a ride with him.
Also…head’s aren’t the only thing he has two of. Just so you know.