First you need to decide what you want--romance or just a friend. If it is romance that is dangerious and have to endure much worst in terms of gossip--even if the boss can be fair about managing things, still others regardless will say that it is because he's sweet on you.

Better to find another place to work before going down that road. If you leave letting him know that you wouldn't mind him calling you from time to time after you leave--well the ball is in his court. If he bites and calls, alls well--but if not and he's not interested better that you findout now then be hurt latter.