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Well, IMO, there is NEVER a guarantee that someone won't cheat.
As for your friends, A should just go for it, and who cares what S thinks? S is still with her boyfriend, so whether she likes Jack or not doesn't matter. She's not with him. I think that S would be waaay out of line if she got mad at A for getting together with Jack.
I also don't think it's fair to hate on Jack for hooking up with S. S has a duty to her boyfriend -- Jack doesn't.
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A hiney bird is a bird that flies in perfectly executed, concentric circles until it eventually flies up its own behind and poof! disappears forever....
-Ken Harrelson
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