1) I would always be worried that he ex would show up with a demon in tow and I'd end up getting possessed. Or that a vampire would kill me. Or ... well, being a Watcher who lives on a Hellmouth has distinct drawbacks.

2) Buffy would radiate waves of disapproval every time we met, especially since I'm only a year older than her. I imagine that would be wearing after a while.

3) He watched Passions with the vampire he kept tied up in his bathtub and disapproves of computers. Much as I love reading, somehow I'm not sure our tastes in entertainment are compatible.