I think your head is totally screwed up, Miss Catholic, but I'm no psychiatrist. I can give you the number of mine, if you're interested. I will say that I think he's more screwed up than either you are or I am.
I once visited a psychiatrist, back in graduate school, in hopes of convincing her I was crazy and needed disability subsidies (one of those periods the parents weren't forking over reasonably). A friend had just gotten it for herion addiction, so I thought I might get some for general lackadaisicalness. Well, I explained how I'd never had a job, couldn't 'handle' work, was afraid to take my car in to have the oil changed, etc., and towards the end of our hour she asked me - I thought in a rather sneering tone - 'do you come from a rich family?' I probably should have lied, but she had me. No disabilty.