Cybrmike, it's such a weird story.
When I met Stein, I'd never seen Ferris Bueller's Day Off and had no idea who he was. My father had just died and he reminded me so much of Dad. I think that's why I liked him initially. Kind of sad on my part, but I'm offering it as a mitigating circumstance.
Gosh, I want to say some good things about him first. He is utterly brilliant, and one of the funniest guys I've ever spent time with. He's a very good writer. His personal, witty and quirky American Spectator column is the kind of thing he does best--his personal essays are much better than his journalism if you ask me. But he's a true Renaissance man. He's a hilarious character actor. He's a lawyer. The guy can do anything. And he turned my head.
Stein can be charming as all get out when he feels like it. But my newnewss wore off soon, I guess. Finally he was just utterly contemptuous of me. Long story short, he's a classic narcissist with every personality disorder in the book. We lived in separate cities, and he never wanted to come up here. I always had to go see him, but he felt free to constantly change our plans at the last minute. I think he just enjoyed jerking me around. One example of many: I was trying to arrange a visit once (he lives in LA), and he changed my plans eight times. If I complained that his shenanigans were making it difficult for me to get time off of work, to arrange my flight, or whatever, he just kept doing it. Sometimes it would work to tell him that someone else in my life was affected. When I told him I thought he should make a decision, already, because my cat sitter was a nice lady and I didn't want to keep jerking her around, a light went on. But he didn't mind jerking me around for some reason. (Can you say passive-aggressive?)
It all became too much when I was expected to be part of a posse of his many other girlfriends and not complain about it. And it was clear he would never stop yakking about how wonderful and beautiful his ex-wife was, and that I would never measure up. One of the most hurtful things he did was to call up a friend once when I was within hearshot, and complain loudly about my childishness. He would also say warm, supportive things to me like, "I wish you were famous."
Stein's financial writing is full of contradictions, as you all have noted, but I want to say it's possible he's actually not a spendthrift. I really don't know. For all I know he's got a huge net worth. Maybe when he said he was worried about money, it meant that he had so much money he was afraid of losing it. It was a long time ago. But it seems to me that his financial advice has more than a hint of "I'm writing this so I'll remember what I need to do myself." I believe writing is therapeutic for him, that his books are mostly for himself. If I find it hard to accept him as an authority, it's because I see him as a person who is struggling to learn lessons which he's pretended to master. I'd be more comfortable if he'd written a confessional account of his money struggles, without purporting to tell anyone else what they ought to do.
He's not a crackpot. He's got some good ideas. I just think he could present them with a little more humility and honesty.