...(hit submit too soon)
The intellectual debate is a diversion to his sadness and vulnerability. He sounds like he might be getting depressed. Of course you want him to feel better, maybe getting him to see how this bad thing is actually good isn't helping. He might feel you (and everyone else) doesn't understand his hurt. When I'm really hurting, it's hard to hear why this is good for me. I usually want someone to agree and say, "Yeah that sucks".
On a philisophical front, Victor Frankyl's "Man's Search tor Meaning" may resonate with him.
