This sort of thing never worked for me in my freewheeling days (now in a monogamous relationship) because usually if I hadn't slept with a guy, it was because I simply wasn't attracted to him. So if he was just a friend and we had never dated, there was a reason! Whenever I had "friends" try to break out of that mold with me it was never successful. But maybe that's something peculiar to me because I always preferred men with mystery when it came to meaningless flings, and good friends just didn't have that, obviously.
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