To me, that's a weird boundary. First, if it's a boundary then she should NEVER discuss her rl with you. Second, she should take more precaution not to run into you (i.e. drive herself somewhere where she wants to walk/run instead of leaving her workplace on foot).

I'm opposite of you, sort of. I NEVER want to see my T outside her building. I like looking at FB pictures, but that's it. I don't care to know what she does. I don't even want to know what kind of car she drives! (I would panic if I saw the model/color of her car on the road). I don't even like it when I see her run to the bathroom real quick. And when the fair was going, I made sure that we weren't going to be there the same day.

I think your T needs to take a little responsibility for this situation. It's not your fault you saw her going out. Though you are still responsible for your feelings.