Hello again,
I think I understand your worry, compounded by the fact that you can't seem to find the right time to have a complicated dialogue with your son. I've been in that situation many, many times, perhaps most of the time these last few years. I think that with complicated conversations, picking the right moment--when you're alone together, face to face, free of emotional distractions, in the right mindset--is extremely important. Actually, I find that face-to-face isn't ideal for me, because it feels too intense; I prefer doing something in parallel, like walking or performing a household task, such as making a cup of tea. You see, if he's not "ready," the conversation will likely not go very well. I get the sense that you understand that.
In practice, I find I have to be very patient to find the right moment to broach a sensitive topic. Sometimes I have to wait months for the right moment. I'd say that's true for my adult BPD stepdaughter, as well as for her dad. There's probably never a "perfect" moment, but I suspect you know what I mean. I guess I'd counsel patience and restraint. Wait for the moment your son mentions a relevant topic, such as stress at work, and you can find a thread to pull. Sometimes I think I'm allowed a dozen words and as many seconds of air time, before a wall will go back up.
Maybe with the new year, you could ask your son what the highlight(s) of the year were for him. I like this question because it's positive, open-ended, and the answers can be revealing. Whatever he says his highlight is, you could underscore how he has a lot of positive things happening in his life, and that you're proud of him for making them happen. That might set you up for a deeper conversation.


