The way I look at it, we're both human beings in the room. I know some schools of thought suggest that I shouldn't care about the therapist, that it's all about me. But realistically, for me, I'm sitting in a room with another person and I do care about them. I probably wouldn't pry, but I would express that I care. When my therapist's grandmother died recently, I told him that I was sorry, because I genuinely was. He shared a few sentences with me and that was that. If you feel something about her situation, I think it's okay to say something that indicates you care and are thinking about her.