Sam watched from the Impala as Dean laid carnations before their mother's tombstone.
It was hard for Sam to feel any grief at the loss of their mother—can't miss something you never had, after all.
Dean had been the one who'd basically raised Sam, because Dad was all too often on a hunt, usually for Azazel—the yellow-eyed demon that killed Mom.
No, what Sam missed this time of year was Jess. He had made plans to make their relationship a little more permanent, and had even bought the ring. Every time he had looked at her back then, he'd imagined what they'd be like as parents—that Jess would be the most amazing mom.
That was what crippled him emotionally, the thought of what he could have had with the girl he'd loved enough to want to spend the rest of their lives together—the girl, it seemed, had dropped right out of the clear blue sky just for him.
He could still remember the first time Jess had kissed him—it had been on a dare from one of her sorority sisters, to kiss the guy she was crushing on. He remembered how she'd trembled, even as she'd grasped his face in her hands and had planted that kiss firmly on his lips.
She had been a little drunk, but then everyone had been drinking. Sam could hold his liquor a little better, simply because it took him so long to get drunk.
The next (sober) day, she'd actually apologized for the drive-by smooch and had explained the nature of the dare. He had been flattered and embarrassed and even turned a little red when Jess had haltingly admitted she'd been admiring him from a distance for the few weeks before.
There were probably more gallant ways to ask the tiny, beautiful blonde out on a date. Somehow, he'd just ended up saying, “So... um, wanna go out? Like, to a movie or something? Together?”
Fortunately, the awkwardness had only endeared him to her more.
The next major step in their relationship had been the day they'd finally moved in together, in a place that was small but cozy. She had insisted on lugging in the items perched in her car's backseat herself. Last thing she'd brought in had been what looked like a picture frame, from his vantage point in the kitchen.
When Sam had come out of the kitchen with two cups of coffee—one for him and one for her, in matching mugs—he'd realized that it was a butterfly collection pressed carefully under glass, and given an artsy flourish with a few pressed flowers.
“I didn't know you collected butterflies,” he'd said.
“It was my mom's,” had been her somewhat curt reply. Knowing Jess's mom had passed away from final-stage breast cancer the year before, he didn't pry and didn't tease her for having a frame full of dead bugs. The following week, he had gone to the jeweler's to buy the engagement ring—not a diamond, that was too cliché. But a silver ring studded with sapphires, as blue as Jess's eyes, and he'd hid it in his night-table drawer to await the right moment.
He could almost see a little boy with her clear eyes and his tousled hair running to her with a homemade Mother's Day card, and Jess being charmed by their son's little work of art.
The ring and the butterfly collection had been devoured by the fire, just as Jess had burned on the ceiling. The life they'd begun to build together was lost in the flames. He had nothing but his memories, and the shattered hopes of the life they could have shared.
Happy Mother's Day, Jess. I still miss you... every day.