The most important thing here is your reaction to these happenings. It definitely sounds like the boundaries have become looser, which does not have to be a bad thing (but it can be a bad thing). I think it's common for boundaries to change over the course of long-term therapy, as trust deepens on both sides. My T and I talk about this. One of my therapy goals is for our relationship to transition to more egalitarian over time, to balance the power as much as is possible/ethical. As a result of my goal and over 500 sessions, we have become more casual/familiar, and he brings more of himself into the session. When I ask him how he is at the start of each session, he will ask me if I want a "therapist" answer or a real answer (I want a real answer). This transition in how we relate is part of my therapy, is thoughtful and intentional, and relates to my presenting problems. It looks a bit like what is happening in your therapy, although with different examples. But what is critically important is that this is to MY benefit, not his, and it is transparent, discussed, and agreed-upon between us. It sounds like your T has slid into this. I know it's hard to talk about, but perhaps something along the lines of, "I've noticed that over time we've become more casual with each other, and I think that's impacting my therapy. Can we talk about that?"