Would you give him a second chance?

I'd actually been cheated on by someone I'd chose to date regardless of the fact that they had cheated on two previous girlfriends. Imagine my surprise when I discovered that he'd cheated on me. He lost a good deal of my trust after that and what's more is that I'd told him in advance that if he cheated on me, he'd be better of confessing than letting me find out on my own. Since then he's admitted that he still likes me but I refuse to date him again because of it so instead, we're friends.

It depends if it was a "one nite stand" or an actual fling. I would consider it if it was a one nite thing, because everyone makes mistakes. If he keeps cheating, then it isn't worth it, because you are going to continue to be hurt each time he regains your trust.