I guess the headphones would be okay. I frequently play with one of my friends I grew up with, it is great to get to chat over the mic. It is almost like being in the same room, though I'd much rather actually have him in the room with me. But if it is someone like your dad who you see often anyway, I guess it would still be spending quality time together.
Can you use the mic through LAN? I suppose you ought to be able to. If you were actually playing over LIVE through the internet you'd have to have a second account, which is another $50 a year.