My sister and her ex boyfriend broke up over five years ago and since then, he and I have remained friends. Once or twice he has alluded to liking me, but nothing ever happened between us. The subject has come up again, and he asked me to dinner tomorrow night. I adore him as a friend and could see that friendship growing into something more, so should I say something to my sister or just wait to see what comes of this date? — Going on a Date Deborah
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Dear Going on a Date Deborah,
Without knowing any of the details about your sister's breakup or where she is in her life now, I would advise you to be honest with her about your feelings for this guy. Even if things are up in the air, I'm sure she'd appreciate your candor — wouldn't you want her to be forthright if the roles were reversed?
You don't have to go into too much detail, especially since nothing has happened yet, but the more honest you are, the easier this situation will be for everyone involved. Good luck; I hope she takes the news well.