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Please write back to me and let me know how this goes. That means setting boundaries and minding their own business.
Also, when and if your daughter and her boyfriend break up please tell your son that he does not have to pick sides and that he should let his sister and friend know that the middle is not a comfortable place for him. I had this happen to me except it was a case of me being miffed at my sister & friend mind you.
I never spoke to my sister for a year after that (laugh) and still don't socialize much since. It wasn't because of getting together, its because knowing them both, I know my sister was just using my friend.
My son recently found out that his sister and friend are having sex and he as the protective big brother is furious at his friend for touching his sister and mad at his sister for "stealing" his best friend. A Baffled Dad Dear Dad, You and your wife seem like two lovely parents with your kids' best interest at heart. But it's nice to know that if you did start dating your best friend, they'll just slide right into family gatherings and skip right past the awkward "meet my family" stage. You've thought about dating them before, then they thought of dating you, but things never lined up right. You have all the same hobbies and interests, and when you're both single, you basically use each other for dates as it is.3. Your family knows your best friend so well and they already approve (they even make sure to tell you that not so subtly). If you just went out with whoever your mom approved of, you'd be married to her old sorority sister's kid.Plus, some girls are very protective of their brothers and don’t want their friends dating them. But if you can’t stop thinking about this guy, maybe you should give it a shot anyway.