More than once, yes. [ Not her proudest moments. ] You're right. I don't particularly judge him; if anything, I questioned where everything went wrong. What I did wrong.

[ She doesn't consider herself to be a Jedi, something she doesn't think now is the right time to tell him. ]

Maybe she felt it wasn't her place to talk about it. It was a dark time for Anakin. She was closest to him, being his Padawan, outside of Obi-Wan and Padmé. As for Kylo, why don't you ask him? I mean, ask about his past, what he means to do here, what he wants back home. Get to know him.