Q: Hi, what are the pros and cons of dating your best friend’s brother? Particularly when you have struggled with infidelity in the past, your best friend knows basically all your dirty secrets, and you value the best-friend friendship.

—Amy

A:Dear Amy,

Well, I mean, you COULD.

But realize, you’re dramatically altering your best-friendship no matter how this potential relationship works out. If this relationship tanks, yes, obviously there’s the possibility that your friend will side with her brother and hold some sort of grudge. Or maybe, as you seem to worry, your friend will confide in her brother about these long past secrets of infidelity, causing damage to both relationships. But even if this relationship goes super well, your friendship will change. You won’t be able to confide in her about the bad or good times in this relationship. She won’t want to hear about that steamy night, and she won’t be able to offer objective support on your argument or listen to complaints about his flaws.

Also, be realistic here. These folks were both raised in the same family, so there’s likely to be a lot of overlap in all the things that you super love about your friend. That could be appealing! Dating all of the best parts of your best friend, only plus attraction. But sometimes kids raised within the very same household can be whoa, very different.

So, sure! You can date this guy. But realize you’re trading in this friendship, at least for the duration of the relationship (if not longer). Is it worth it to you?

—Liz Moorhead

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