Which is interesting because this episode was sort of the turning point between Dean’s “I got a year to live” DO ALL THE THINGS mission, and taking his one year to live far more seriously. Heck, he showed up at Lisa’s thinking of her as “Gumby Girl,” and discovers she’s settled down into a responsible life and caring for a child that he suspects for a hot minute could be his…
Then during his time with her, prompted by wanting to reconnect with her for purely selfish sexual reasons, he bonds more with Ben than Lisa, and he never even gets to have his bendy sex with her.
(Heck Lisa even lives in a “gated community” of the sort that would normally keep “riffraff” like Dean out. But it doesn’t keep out the monsters.
Another thing of note: Sam gains folks’ confidence left and right. We know he’s good with interviewing witnesses, but heck if he can lie to Dean to save his life…
He’s sitting in a cafe talking to Bobby in secret about getting Dean out of his demon deal, but when Dean walks in and Sam hastily hangs up and slams his laptop shut, Dean asks what he was up to. While sitting in a cafe, Sam says he’d just ordered a pizza. Because that wasn’t shifty and suspicious.
(pffft, when Ruby shows up, Sam asks her where she got the knife that can kill demons, and she says Skymall…)
So Dean “Love Me Some Pie” Winchester shows up expecting one thing, but instead is served something entirely different, and he just rolls with it. And eats the cake.
So here we have Dean dealing with some of the issues that have traditionally fallen to Sam. At this point Lisa knows nothing about Dean’s “job,” or the supernatural. His long-ago bendy weekend with her didn’t involve any sort of truth about who he was as a person. It wasn’t real (just like the fact he dreams about that unreal situation with her in 3.10. He wasn’t in love with her, but this ideal of her…). He tries to protect her from this monster. At first she doesn’t even realize that her son’s been replaced by a changeling, and she doesn’t buy Dean’s multi-layered deception to try and protect her from ever coming in contact with the supernatural, but he was too late.
The supernatural had already affected her life though, whether or not Dean had been there to protect her from it. His coincidental presence there (this time, at least… it was a different story in s6) was what SAVED Ben and Lisa from the monster.
(which is convenient, because Dean’s just sold his soul and sacrificed his life for Sam, and here’s proof that his life DOES have more meaning than just saving Sam. He wasn’t a “curse” on the lives of the people he comes into contact with the way Sam always felt. He saved them.)
Then we have Sam’s research into the Campbell family and friends who were systematically wiped out by the demon, prompted by Ruby’s comments to him. And then we learn Ruby’s a demon, and she comes off like a drug dealer offering a free taste while holding a HUGE carrot just out of reach. Of course Sam was tempted:
RUBY (laughs) Don’t you get it, Sam? It’s all about you. What happened to your mom, what happened to her friends. They’re trying to cover up what he did to you. And I want to help you figure it out. SAM: Why would you want to help me? RUBY: I have my reasons. Not all demons are the same, Sam. Not all of us want the same thing. Me? (shrugs) I want to help you from time to time. That’s all. And if you let me, there’s something in it for you. SAM: What could you possibly— RUBY: I could help you save your brother.
(while I was typing this, 3.03 started, so I’m watching Sam and Dean argue about this decision to work with Ruby… where Dean absolutely believes she’s lying, Sam wants so badly to believe she may be able to help Dean, but they’re distracted from actually finishing the argument because the phone rings… and the ghost of John Winchester rears its ugly head… Nevertheless Dean is SO not on board with working with Ruby, and thinks Sam’s not in his right mind for thinking they could “use her” and retain some sort of upper hand in that situation.)
(because that doesn’t sound ANYTHING like Sam’s delusional deal to work with the BMoL in order to “use their resources” and thinking that he had the upper hand in that situation >.>)