OK, first I have to say - LOVE Dean getting caught out watching Oprah. Love his reaction to Sam calling him on his comment, his total lack of comeback or denial or anything other than a delayed 'crap, I can't believe I said that out loud' expression.
OK, next I have to say - I would like Dean in a towel, please.
All right, meta. I'm going to focus on one thing from this ep, because it's what I find most intriguing, even though there's something else that factors into the entire season arc, which is Dean's role in the family unit. Suffice to say this episode holds a key scene in showing how Dean acts and reacts to Sam, how he does what he can to hold the family together even when the family doesn't necessarily act like it wants to be held together. For Dean, family comes first - he even says so, explicitly.
But since this theme gets touched on a lot, in other eps, I want to look at something else: Dean's comment that a normal life would drive him nuts.
They're in the housing development and Dean gives a good description of what it will look like when it's inhabited. Manicured lawns, husbands coming home to housewives, all the neighbors living the same sorts of lives day after day. Dean's comment that he'd blow his brains out speaks, I think, to the sheer boredom he would encounter living such a life.
Compared to the life he's used to, even without the actual hunting evil monsters, Dean lives a rather more wild life than your average suburbanite. He lives on the road, plays pool and poker and darts for a living, running credit card scams and getting arrested occasionally, and enjoying the company of ladies (whether or not he sleeps around a lot, he does definitely have one night stands, sometimes with two girls at once. *cough*.)
Even if you don't consider shooting shotguns and setting fire to graves and driving his car through houses, Dean lives an action-filled life. But even all that aside, he does have more important things to do. He's said it to Sam, he helps people by hunting evil monsters. He kills and destroys evil monsters, in part as revenge for what happened to his mother but also, I think, in part simply because he can and he's good at it and he likes it. Dean enjoys most of his life, even when there are deeper things at work beneath the surface. He has darker emotions, even when he doesn't readily show them, but he also manages to enjoy himself -- genuinely enjoy himself, not just endure or get by or try to distract himself or bury himself in pleasures of the flesh in order to escape his life. Dean is a guy who, if given the real chance to have a normal life -- wouldn't take it. He likes his life. He may not enjoy every aspect of it, but his cocky smile and calm demeanour even when things go 'wrong' demonstrate a basic attitude that is *not* one that says he hates his life and wants something totally different.
He does want things he doesn't have, and some of those things are "normal." But those things are often simply things of luxury and pleasure -- a steam shower, when he's used to motel showers. Free food, which is always a plus when you have no regular paycheck. He takes these things when he can get them -- but there are other things he doesn't ask for. He doesn't mention wanting a home, a permanent place to settle down. He doesn't talk about wanting someone to go home to (though we learn later about Cassie, it's an open question if he would have settled down if they'd stayed together.)
Dean says he would take his family over "normal" -- he acknowledges it wasn't necessarily a happy, comfortable childhood but he doesn't harbor resentment the way we see Sam doing. He doesn't criticise what they went through, and more or less comes across as agreeing with their dad about the choices he made in raising them. Dean would have chosen to learn bow hunting over playing soccer -- at least as we see him in S1. A 12 year old Dean may have chosen otherwise, but Dean seems unaware of, or unwilling to demonstrate, an awareness of this. he acts like he always agreed with their dad. Regardless, at this point he seems to understand their dad's choices, and stands by them.
Part of this acceptance may come from denial about what he should have wanted as a kid -- the "normal" things Sam wanted. It may come from Dean growing up too fast and truly understanding that other things were (at least for their family) more important, like hunting monsters. But whatever the cause, at this point in Dean's life, we see him honestly choosing the life he was prepared for, and actively desiring it over other options.
Contrasted with both Sam and John, who seem forced into it by their pain and need for revenge, Dean seems to be happy with his life, and even if there were no hunt for the Demon that killed his mom, I think Dean would still be a hunter, still be just as driven, and still be more or less the same person. The Demon drives Sam and John, shapes them and gives a focus to their lives that shows up as a quest for vengeance -- thirst for blood, as it were. Dean's thirst isn't for blood. He wants things like justice, and protection for those who can't protect themselves, and he wants to have fun, and he wants his family to be part of his life.
All of those things are, in fact, rather normal. The environment in which Dean pursues those things isn't normal, but they are understandable, heroic, and more or less healthy mental attitudes. Compared to the obsession we see in John and the conflicts we see in Sam, at times you could say Dean is the most normal -- most well-adjusted member of the family.
Er, though with Winchesters that isn't saying much... ;-)