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I think he's totally covering his bases. If she was just a friend, I would say swallow the jealousy and move on. But clearly both of them have had romantic feelings that have never um...blossomed, for whatever reason, into a real relationship. I hate "her or me" ultimatums - they seem so insecure and who wants to be on the losing end of that - so I think instead you might want to go back on a break with each other. The whole "if you love something set it free" thing...sounds like right now he has the best of both worlds - a kind, understanding, putting-out girlfriend, and a slutty attention-giving ego-boosting "umfriend". Don't "make" him choose, but don't put your life on hold waiting for him to make up his mind while it's making you miserable.
In a way, you've already done this - while you were broken up, you gave him permission to date her, and he chose you. If you still don't trust him, maybe he's not the guy for you.
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"If ten million people believe a foolish thing, it is still a foolish thing."
- Anatole France
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