The Winchester men have complex relationships with the women they encounter as they do their job. I find it interesting that Sam seems to have more relationships than Dean, despite having lost Jessica and Dean so clearly longs for a family. Why, I wonder?
First we have John and Mary. John clearly adored his wife, still wearing his wedding ring 22 years after her death, was so driven to find her killer that he took his boys on the world’s longest road trip, stripping them of their home. Did he look at his children and see his wife, knowing he had to protect them as he hadn’t protected her?
No doubt he had encounters with other women later, as apparently the episode “Jump the Shark” will reveal. But Mary was his be-all and end-all love. I wonder if he ever discovered she didn’t trust him enough to tell him the truth about who she was.
Sam had a normal life for a few years, something he always longed for. He had a beautiful girlfriend who supported him in a way his family never did, who encouraged his strengths. Losing Jessica in the way he’d lost his mother crushed him. He knew he couldn’t have a normal life until the Yellow-Eyed Demon was destroyed, and so he went on the hunt.
He had an almost kiss with Lori in “Hookman,” and shared things with Meg as he hadn’t with anyone since Jessica’s death in “Scarecrow.” In “Provenance,” he met beautiful, smart, charming Sarah. When he tried to give her the whole, “People around me get hurt,” she essentially told him to snap out of it.
One of my favorite exchanges in the whole series is between Sam and Sarah.
Sarah Blake: [watching Sam and Dean dig up a grave] You guys seem to be uncomfortably comfortable with this.
Sam Winchester: Well, this isn't exactly the first grave we've dug. Still think I'm a catch?
(Funny, I just realized that every one of those episodes is on my iPod.)
Sarah is the first girl he kisses after Jessica dies, months later, remaining faithful to his dead love all that time. I loved Sarah, and would love to see her return, though I know things would be way different between her and this grown-up Sam.
We don’t see Sam in relationships in season 2, until Madison. Ya know, the werewolf chick. He babysits her and resists her efforts at flirtation, not knowing if she’s a monster or not. And when they are successful (they think), he’s more than willing to celebrate by pinning her to the wall, and….guh. The arms make their first appearance.
And then he realizes she isn’t cured. She’s still a monster and he hunts monsters. When she asks him to end her suffering, he mans up. And it knocks him back into himself, more unwilling to risk himself than ever.
I think that’s why he chooses to continue his sexual relationship with Ruby. She knows what the stakes are. She knows what she risks. She can protect herself. In Sam’s eyes, she’s safe. Still, I don’t think he lets himself care for her. That she’s a demon has a lot to do with that, of course, but I think he’s just already given too much of himself. He knows there’s no light at the end of the tunnel, that there will be no happily-ever-after. He’s resigned he can’t go back to a normal life, and so he settles with a relationship with Ruby.
For all that Dean wants a family, he doesn’t let himself get involved with women the way Sam does. Yes, he charms them, but his more meaningful relationships were in the past-Gumby Girl (okay, that was mostly sex, but he did think he had a kid) and Cassie. With Cassie, Dean broke the Golden Rule of the Winchesters, don’t tell ANYBODY the truth. Dean, who never went against what his father said, told Cassie the truth and she freaked. Showed him. You see he doesn’t have any real relationships with women now. Heck, how can he?
She believed him easily enough when she needed him, though, right?
I’ve heard some people call her whiny, but I liked her enough. And that love scene was Smokin’. I ended up buying the Bad Company CD for that song.
I don’t even want to talk about Jo, because that was just such an unnatural pairing, so forced. I liked Alona Tal in Veronica Mars, but loathed the Roadhouse women. Yeah, don’t want to talk about that.
I’m not sure if Carmen, from “What Is and What Should Never Be,” counts. After all, she was a product of Dean’s imagination. She was a down-to-earth girl, though. Wouldn’t it be lovely if Dean did get a girl like that, who understood him and kept him on an even keel?
And then there’s Anna, the Angel. Again, I felt this relationship was a bit forced, though I liked the conversation they had on the hood of the Impala, when she talks to Dean about following the orders of a father she didn’t know and couldn’t understand. What kind of relationship do you think the two of them might have when she returns?
I know I didn’t do justice to Dean’s relationships, and I’m sorry. Maybe you could help me flesh that out?
Which relationship do you think met each boys’ needs best? What kind of woman do you think each boy needs? Why do you suppose Sam gets more love than Dean?
