Thanks for sharing all that and I'll certainly consider a follow-up piece. I think the short version is, does the person use their time with you holding space to process and try to move through what they are feeling, or are they just stuck on rehashing the same things over and over again (which is almost a form of addiction to pain). This is not to say that everything should be released or cleaned up in one episode, but there does need to be some effort toward coming to terms with whatever is going on, making a plan for different choices, or otherwise attempting to get back to some sort of equilibrium.

This doesn't sound like what your brother was doing AT ALL, nor does it sound like he has any respect for your feelings or boundaries. That doesn't mean it isn't still hard to have him go out of your life again. My condolences on the loss of your grandmother as well.