I don't think you can know what she's thinking unless you ask her. Looks on people's faces can't be read reliably as you can't know the thoughts behind then. Even if she looked disapproving you don't know of what, she could be thinking of something she did that she disapproves of or it could be a look meaning something else and just looks disapproving to you.

I would tell her how uncomforable you are telling her these things (maybe print the post and take it in) and how you feel like she might be judging you and then see what she has to say? I spent a long time with a married man who was 20 years older than I was, such relationships probably won't get you anywhere/anything you want in life. I don't know that your T is judging you, she's probably is just thinking it is too bad you pursue such relationships.

I don't know many men who wear wedding rings; that's not a way to find out if they're married and/or persuing men that much older than you are probably isn't going to work out anyway.