If you spend enough time with him, you'll learn a lot of the answers to these questions. But that's what it takes . . . a lot of time. You can't gaze into a crystal ball.

This guy is kind of a jerk. I wouldn't be all that interested in getting to know a jerk better. Who cares how and why he became a jerk? Like - are you going to become his therapist and try to coax him into not being a jerk? Have at it, if you can't find anything better to do.

In the end, he'll still be a jerk. Eventually, people will tag you as the girl who hangs out with jerks.