I hate to say it, but I'm dumb enough that I kind of like being in touch in some way with everyone who's paraded through my life, and I'm centered enough that it doesn't particularly f--- me up. So, thought the guy sounds like a dick and doesn't deserve whatever emotional satisfaction he might get from talking to you again, do whatever you feel comfortable with. If you're just going to obsess just because they guy has exchanged a few emails with you, then screw it, but if it would amuse and not upset you to hear more about his shitty life now, then answer him. Just don't be too nice.