Rainbow Child - I don't know how to thank you for your incredibly helpful explanations. While I may not be able to truly understand, it helps immensely to read of your experiences. Thank you so very much for taking the time to help me.

Based also on some things he said, and thinking about what you described, I get the impression that he somehow enjoys putting himself in difficult situations because having to scramble to make it through gives him something to focus on. As soon as everything is calm and peaceful, he has time to wallow in his thoughts and he starts feeling as if life is pointless since there's nothing to fill this emptiness he constantly feels. Partying and drinking and talking to strangers might offer some temporary relief/distraction, but it never lasts very long - starting a new life from scratch will give him something to keep busy for a while longer. And then, as soon as he's settled, the cycle will start again. I'm not sure if this makes any sense, but it's the impression I'm getting.