Okay, let me back up a bit. Yes, I do enjoy discussing people's issues, largely as a problem solving exercise and because I like trying to figure people out. If I had had something to do that day, I would've told her to get lost. I have no problem establishing boundaries. The problem is that I sometimes indulge in unhealthy relationships out of boredom, even though I know it's going to end badly. It's like waiting to watch a train wreck. I'm getting the feeling that this is one of those cases.

There's still a lot of value to be had out of this friendship. We're planning on becoming roommates (along with a third person) because rent for a single bedroom apartment is way too expensive. Also, we have a lot of similar interests, which can be hard to find. So my question is -- can this be a healthy friendship, or should I trust my instincts that this is a train wreck waiting to happen and start throwing up walls asap?

Also:
It's the same person.