Styling tips are not going to help here; he's got to get over his obsession with his hair. The problem is inside his head, not on top of it.
(so clever I am!)
You know how folks who are afraid of spiders have that therapy where they force themselves to get a little closer to spiders, ultimately ending up holding one for a while? I think you would benefit from a variation of that. And when you catch yourself thinking about your hair, *conciously CHOOSE* to stop thinking about it. Switch to something else. Over and over and over and over again, as needed.