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.

– Meredith

Readers? What boundaries would you maintain? Also, what would you ask the brother at this point? (Also, no Jenga in this letter.)