It's really nice when you don't even have to think about can I/can't I look, you just do what feels "natural" and that's okay. That's when you'll know you're really doing well, when all the little "worries" about trash cans :-) and looking someone in the eyes or not won't even occur to you. I never did learn to ask my T "personal" questions but toward the end, she shared a lot more personal stuff as part of our conversations. She got "realer" to, getting "annoyed" at me occasionally when I'd do something I'd grown out of, that sort of thing. And it all worked out okay. I quit worrying she'd leave me (or throw me out :-) and just be a bit disappointed in myself for annoying her, or sad, or amused and touched because I was under her skin enough for her to get annoyed and she trusted me enough to show it.