Jess likes Sam because he can take care of himself, in the human sense. He doesn't know how to gank a ghost or kill a werewolf, but he's six-foot ginormous with an ex-marine for a father. He knows how to defend himself from people – and I can defend you too, Jess, he says earnestly. She thinks it's sweet and giggles, because while she knows how to take care of herself she can appreciate the gesture. And the way his nose crinkles in confusion is enough to set her laughing even more, until Sam smiles and wraps his arms around her in a giant bear hug.
She admires him for his devotion to his family. To the father that's a little rough around the edges and forgets sometimes that kids aren't the same as boot camp trainees. To the brother who gets in trouble because he drinks a little too much and fools around a lot too much, but loves Sam as much as Sam loves him back. To the mother who tries to smooth out the edges of three grown men so their personalities don't leave grating scars on their relationships. His family is headstrong at best and combative at worst, and she admires the effort all four of them exert trying to make sure those independent streaks don't tear them apart.
She loves him because he bakes her cookies and sits with her in the library so they can study together and invites her over to family holidays, though he tacks on a huge blaring disclaimer to the invitation. She rolls her eyes at his melodrama and comes with him to Thanksgiving, smiling wistfully at Mary and John and brushing off the half-hearted attempts Sam's brother makes to flirt with her. The Winchesters, happy for new blood, regale her with old family anecdotes told so many times the story can jump from teller to teller seamlessly, each person adding their own flair to their part. It's domestic and open to her and everything Jess left hunting to find. She clutches Sam's fingers tight under the table and feels herself happily smiling until her cheeks are sore, wishing with all her heart she could just sit at this table forever.
At Christmas, a few years after her first Thanksgiving with the Winchesters, when she's wearing a ring Sam had spent a whole month scouting out – though Jess will never let on she knew where he was going – Mary pulls her aside while John and Sam and Dean are outside shoveling snow from the driveway. Mary examines Jess critically, noting the bags under he eyes and the slouched droop of her shoulders. "Are you all right, honey?"
Jess has been having nightmares recently, of Sam dying from supernatural creatures and her being too out of practice to do a damn thing to save him. She's having second thoughts of tying herself to this wonderful, normal family. She's thinking of all the horror stories she heard growing up about hunters who tried to settle down and failed. Jess doesn't say a word, but her future mother-in-law looks her face and says softly, "oh." Mary blinks sadly at Jess before looking away. She inhales, seems to quiver a moment before resettling into her bones. Then she looks back at Jess and all of a sudden Jess' lungs empty because she recognizes that look. Only it can't be; Mary Winchester can't be a hunter. Hunters live hard and die young and leave broken families in their wake. They don't have normal apple pie lives and a loving husband of twenty five years and two successful kids.
Mary looks at Jess' expression – meandering somewhere between gobsmacked and incredulous – and clasps her on the shoulder, looking Jess directly in the eye with an raw intensity she's never seen before in the woman. "It is possible, Jessica Moore," she says. "Don't let anybody tell you different." Jess opens her mouth once, twice – but nothing comes out. Mary shakes her shoulders gently to drive home the point. "It is possible to have a happy life, and I hope you find it with my boy." Jess meets her eyes, listening to the muffled conversation of the Winchester men outside, and nods slightly. She thinks, when she's not plagued by baseless nightmares, that she can find happiness with Sam, too.
Mary smiles and releases her shoulders, stepping back to give both of them some room. She exhales slowly and appears to dissolve back into the loving mother she's always been. Only this time, Jess can recognize the little hints of Hunter-Mary on the corners, pieces of her personality she'll bring out when her boys are being especially ornery or unreasonable. "We're the ones who got away," Mary says, and Jess feels the knot of anxiety loosen in her chest. This thing between her and Sam isn't just a prolonged delusion or an aberration. We, Mary had said. She wasn't alone in wanting out of the life. Jess smiles, and Mary returns it before picking up a box of instant hot coco. "I think those boys have been out there long enough, don't you?" she asks.