I think it's quite in keeping with Dean's character for him to take the heartbreak and loss all onto himself and to try to fix something he believes he broke. Was it skeevy? Maybe. But what was the alternative?
Ben saw his mother possessed, saying horrible things to Ben and to Dean, calling her a whore as the demon held a knife to Ben's throat. He saw his mother mortally wounded by the demon, had a gun thrust into his hands by Dean while Dean carried his mother out of the building. Ben shot humans possessed by demons and watched his mother bleeding to death in the hospital. With Lisa saved and their memories intact, how could Dean make it right? How could he leave them broken and afraid? And he had to leave them.
Yeah, Castiel saved her life but not the mental anguish, fear and trauma that would have haunted them for the rest of their lives. Dean's act, selfish and selfless as Juliebird pointed out, gave them back their lives.
He broke my heart with what he did, but IMHO it was totally a Dean thing to do. Sam called him out and it was totally a Sam thing to do. Still, Dean's been sacrificing his own happiness since he was four years old. I wouldn't expect anything less from him.
What Dean did was wrong, possibly unsafe, and totally in character.
This. I'd emphasize the "possibly," though, because I'm not sure without Dean in the picture, and given where the "battle" ended that Lisa and Ben would have been a target anymore anyway.
The moment really broke me, for mostly for Dean (and JA played it so subtly and beautifully broken himself). Objectively, I knew it was the writers putting a period to that storyline and those characters, and while I know it was wrong, I can't get worked up about it because I also believed Dean would do it, and why.
For those who read wincest:
aggybird's Big Bang entry for this year: Sam and Dean Winchester: Unicorn Hunters. Features two Queens of the Faery, a Phouka of intriguing origin, a green Knight, and evil fire-breathing unicorns from another dimension with names like Skullcrusher. I laughed through the entire thing.
It's probably wrong that I now want to write Dean/Cas, just so I can have a section like, "Cas tastes like peanut butter, banana, and bacon sandwiches. If Cas is somehow using his angel powers to figure out Dean's favorite food from the summer he lost his virginity to an Elvis-obsessed college girl, it's crossing the line into creepy stalker territory, and if he's not, then man, angels are weirder than anyone would think."
Only, you know, not typed out on the fly in a comment box.
Bwah! I'd love to see a subsequent taste test, to settle the weird vs. stalker conundrum, except that Dean thinks pretty much all other angels are dicks.
Ha! I know whenever I read scenes along those lines, I'm thinking "People, unless a can of whipped cream is in the picture the best you can realistically hope for is the taste of clean skin and soap!"
Skin isn't usually what is being tasted in my cites.
"Castiel tasted like exhaust fumes and ripe dumpsters baking in the August heat and fishmarkets."
The funniest part is, aside from Famine-induced cheeseburger cravings, Cas doesn't eat. Or drink. He's not going taste like much.
Those Castiels are the ones that taste like springtime and fog and rain, I'm assuming.
AU Cas is very tasty too...weirdly more tasty than AU Dean. I think it's a function of PoV, maybe? But I've only come across 1 or 2 tastes of Dean, and 30 or so tastes of Cas so far.