I know it sounds bad, because I'm not a psychologist or anything, but when you've grown up with someone through all the changes in their life, you can tell when they just aren't happy. I don't know how to mention it, or how to explain myself when he asks me why, because it seems I'm projecting what I think is important onto him. That being serious introspection. And I say this, because yesterday when I asked him to read through a "Conversations with..." article, he finally told me he doesn't like Personality assessment stuff because he doesn't know the answers, he doesn't know how he does this or that, or what he's like most of the time.
That would be all well and good, for someone who doesn't care. But he said is makes him depressed that he can't answer, which is much different from just thinking the tests are silly.
So, how can you explain this to someone who's so sensitive about the subject of their own personality in the first place??