Angela made me wonder if she would be a Sam or Dean!girl.  So, here's a post explainin them as best I can.  Obviously, that means this post is long.

Since she thinks she'd be a Sam!girl, let's start with Sammy.

Season One:
Pre-season one, Sammy left Dean and John (their dad) to go to school.  In college, he was brilliant, about to get accepted to Stanford law school with a full ride.  And then Dean shows up in Sam's apartment and says that their dad is missing.  Sam, the marvelous person that he is, goes to help on the condition that he get back in time for his law shcool interview.  When they don't find papa on that first hunt, Sam still insists on going back, until he realizes that his girlfriend (for whom he had been shopping for engagement rings) had been killed by the same supernatural thing that had killed their mother, launching their family into this in the first place.  He leaves with Dean and never looks back, looking for revenge for Jessica (and Mary, their mom).
On the road, gangly and brilliant and cute-in-the-geeky-way Sammy is the brains of the operation.  Sam really cares about everyone.  Sammy is the heart.  (Which is a statement that I may or may not contradict when I explain Dean.)  Sammy is simply a sweetheart trapped in a life of death and darkness by his father, whom he has a very convincing love-hate relationship with.
When they finally do find their dad, we see just how alike Sam and papa are, which throws all of Sam's good qualities (which I personally feel like John lacked, but there are John!girls out there who would slaughter me for that) into contrast.  They are both being driven by this deep, dark hatred, the need for revenge. 
And now to learn about Sammy the psychic.  Hahaha.  Because that is what's really important.
When Sammy was 6 months old, a yellow-eyed-demon bled in his mouth, making him a psychic child destined to lead an army of demons (or more than that, as we may see soon).  This demon also killed Mary and Jessica.  YED, as he is fondly known by those who cannot spell his real name (Azazel), made a few of these demon children.  Anyway, Sammy has "death visions," premontions of people about to die (usually with something to do with YED).  They started as dreams (including dreams about his grilfriend's death), and then evolved into visions while he was awake.  He could train himself to do other cool psychic stuff (like a Jedi, and you'll see about that in season 4).

Season Two:
(I warned you that this would be long.)
Sammy was the stabalizing force in season two (which will make more sense when I explain Dean in season 2).  He was still geeky and smart.  His hair looked better, and he was a little less gangly.  He's still driven by a need for revenge, but it's not just for mom and Jess now, because papa died in the first episode of season 2.  A lot of psychic stuff happens.  Sammy dies.  He comes back (explained in Dean), but he's not quite the same Sammy.  He is not as caring, more shoot-first-ask-questions-later, overkill, dark and on his way to season 4 (explained soon).

Season Three:
(Are you still reading, hon?  I know it's long, and we haven't even started Dean yet.)
Season three began Sam's road to the dark side.  It was in season three that he met Ruby.  It was in season three that Lilith, the main bad guy of season four, was introduced.  (I suppose I should explain them.  Ruby and Lilith are demons.  Ruby can remember being human and "wants to help Sam defeat the evil side -- Lilith."  Lilith tends to possess cute little girls and kill people senselessly.  She holds contracts made with the crossroads demon [whom Sam kills in season three].)
All of season three, Sam is driven by the need to keep Dean alive (revenge has been handled all ready ... all explained in Dean).  Sammy is definitely not gangly anymore.  He's not as smart, either.  Ruby seems to have infected him with the stupid-decisions-disease.

Season Four:
(This is the season we are in the middle of.  Almost there!)
Working with Ruby, training to take out Lilith.  He can now exocise demons with his mind (no more visions).  Between seasons three and four, Sammy had to grow up a lot and learn how to live without Dean (explained later).  He had to learn how to make survival not about caring for his brother and more about finding a way to take revenge.  He had to make Dean unimportant in the grand scheme of things.  Which explains why he seems so cold toward Dean when Dean comes back at the beginning of season four.  He still cares, he just doesn't quite remember how to.  He is still infected by the stupid-decision-disease, until Dean comes around and smacks some sense into him.  Literally, in some instances.

You ready for Dean now?  Should I take a break, maybe?  Post Dean later?
Nah, here's Dean:

Season One:
Dean is driven by his love for family.  He is the protector, the one in charge of keeping them all safe.  His family is his weak spot.
When Sammy was 6 months old, Dean, 4 years old, carried him from their burning house while John attempted and failed to save Mary.  Ever since, Dean has been saddled with the responsibility of raising Sam, protecting Sam, looking out for Sam.  His father treated Dean like a good little soldier who had no real meaning or self-worth, and so Dean began to think that over the years.  It was so engrained in him to care for Sammy that he forgot how to care for himself, how to want something for himself, and how to love himself.
Dean is not stupid, but he is not as smart as Sam either.  This is because he spent every waking hour caring for Sammy instead of using his brain in school. 
He's the rugged hero, the shoot-first-ask-questions-later until Sam (who cares about everyone, not just his family) reminds him that sometimes this strategy doesn't work.
Now, this doesn't mean that he doesn't care about other people.  Dean spends his life saving other people.  He's just more concerned with his family, and his family would come first.  (Put to the test, Sam would probably be the same way, but it's more evident with Dean.)
Ooo, and his amazing muscle car, leather jacket, and classic rock cassette collection.

Season Two:
He is a mess.  Papa Winchester sold his soul to YED so Dean could awaken from his coma.  The man he'd spent a year searching for, the man who had formed Dean into the hunter he was, the man he would die to save, had died to save him.  "What's dead should stay dead."
Until, well, Sam's the dead one.  Because then Dean can be a hypocrite.  Dean sells his soul to bring Sammy back, and is given one year to live.  He then kills YED.

Season Three:
I think I forgot to mention in seasons one and two that Dean is the joker of the two, but he is.  He's constantly making jokes and alluding to movies he's seen, which helps to provide the comic relief in some of the more difficult episodes.
Anyway, in season three, he's constantly joking.  It's what he does when he's scared.  And, going to Hell seems like a pretty terrifying thing.  So, for the first half of the season, he shrugs off the possibility with jokes.  He takes unnecessary risks because he figures one year to live, it's not worth being precautious.  (A note about his deal: if he tries to get out of it, he'll still die, and so will Sammy.)
By the middle and end of the season, he finally realizes that he doesn't want to die, and he and Sam and Bobby (kind of their father-figure, older hunter, role model figure) begin to search for ways to get him out.  Sammy turns to Ruby for answers, but Dean won't hear of Sam using his psychic powers.  Those freak him out beyond compare; John told Dean before he died that Sam's powers were dangerous and that, if Dean couldn't control Sam, he'd have to kill him.

Season Four:
He's back from Hell!  Castiel, an angel, was ordered by God to drag Dean out of Hell.  So he's pretty important.
He never really believed in angels (there was an episode in season two that I probably should have mentioned, but forgot.  Anyway, it was about an "angel" which turned out to just be the spirit of a dead priest.  In this episode, we learned that Sam prays every day, Dean doesn't believe in any of the good supernatural stuff, and Mary used to tell them that angels were watching over them every night [and that was, in fact, the last thing she said to Dean before she died].), so Dean's beliefs are thrown into question.
So far, season four has been Dean trying to get Sam not to use the psychic powers anymore.  Dean's been very emotional, which he would never show before, really.  But, after what he experienced in Hell, he deserves it.  Sam and Dean have been having some serious issues that have led them to nearly kill each other once (they were under some kind of "spell," for lack of a better word).

Well, those are the boys.  What do you think (if you read it all)?
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