I am 26 years old. My best friend's older brother got my contact information and has made comments about a possible "us" in the future. We are getting to know each other. I like him too, but we have yet to become official.
He has been generous, buying me things every opportunity he gets. My friend learned about some things he bought me – or has talked about getting for me – and she was hurt because she felt he did not offer the same kindness to her. Do you advise me to stop telling her things concerning her brother? I don't want to ruin my relationship with her or him. It's special for me because when I fall for a guy, I fall pretty hard and get so obsessed with him I literally have to catch myself. I can say what I feel for him is gradually evolving into love.
Your friend doesn't need updates about gifts and romantic gestures. All she needs to understand is that you're pursing a romantic relationship with her older brother, and that you'll do your best to maintain boundaries so nothing gets in the way of your friendship with her. If you want to talk about all of the cute things this man is doing, call another friend. Anyone who isn't related to him.
It also sounds like you need to talk to her brother about what the two of you are doing. You say he's talking about the future but that you've yet to make it official. Is this some sort of early courtship phase? Are you both hoping for more? You don't need to define the relationship before you're ready, but you can let him know that getting to know him has become a priority. You want to find out what happens next. You can tell him to do more than hint.
Also tell him about the boundaries you're setting with his sister. That might clear up some confusion about who knows what.
Readers? What boundaries would you maintain? Also, what would you ask the brother at this point? (Also, no Jenga in this letter.)