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Meet the Wise Guy. He’s got advice to give and questions to answer, so send in any and all problems concerning the opposite sex. What makes him so qualified? He’s been a boy his whole life, so he knows exactly what’s going through your crush, boyfriend, or best-guy-friend’s dumbhead. Ask him!


Last week, my best friend (“Anne”) told me she had cheated on her boyfriend of five months (“Doug”) with this guy from our high school. I promised I’d keep her secret, but Doug has been a friend of mine almost as long as Anne has, and I feel like I’m betraying him by staying silent. On top of that, my parents split up because my dad cheated on my mom in the past, so I really want to tell Doug what happened. Should I?

Sure — if you’re prepared to lose your best friend. Anne trusted you enough to give you information that she didn’t feel safe sharing with anyone else. If you betray her confidence, there’s a good chance she’ll never trust you again, especially if she loses her boyfriend over it (which she will, by the way).


If you really want to help your friends, tell Anne she should break up with Doug. If she cheated on him, her heart’s definitely not in the relationship and she should end it before someone gets hurt. I know you feel loyal to Doug, but he doesn’t need to know he was cheated on. I’m all about honesty, but I think that full disclosure would do more harm than good in this case. Doug would be devastated, and he might even have problems trusting girls in the future.


And look: what your father did to your mother is absolutely inexcusable, but this is a completely different situation. Anne cheated on a high school BF that she’s been with for five months. High school relationships just aren’t made to last. It’s a time when you’re learning how to relate to a boyfriend or girlfriend, how to give and receive affection, how to deal with temptation and jealousy — and everyone makes mistakes along the way. So cut Anne some slack, especially if you genuinely value her friendship. Best friends can never really be replaced, and I hope you don’t find that out the hard way.

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