I have a great T and we often talk about personal things. I often ask him "personal" questions, but always start with "I have a question for you, but if it's too personal or makes you uncomfortable answering, that's fine..."

He has yet to not answer one of my questions, but he is given a simple out if needed. Let's face it, even though you are in "professional" relationship with your T, it's also one of the most "Emotionally Intimate" relationships you'll ever have... It would only be natural for you to care about them, especially if you've been in long term therapy.

I would just take a deep breath and next time you see him, tell him that you missed seeing last time and hope everything is ok now...this gives him an opening to share with you (since you already know a little) or to pass it off (just don't take offense if he doesn't share, he's human too and it might be something too pain for him to talk about at this time)