He wasn't sure how it ended up in his hands, why he began to finger the frayed corners and trace the outline of the image. Somehow the small, wallet-size portrait was right there in front of him. All of these years it had remained intact and clearly identifiable, her hair was still so blonde it shone and her smile was as genuine as he had ever seen it. Or at least that is what Sam hoped he remembered, eight years had put a haze over every memory of Jessica he had and that was what probably frightened him the most when he pulled out the picture. It had been stuffed into one of the numerous pockets that decorated the inside of his well-worn wallet, tucked so far back he had forgotten he carried it with him. The picture was something that had been pulled out countless times in the first few years since violent act that took his girlfriend's life, it was the only thing that kept up his unforgiving need to hunt as they tracked Yellow Eyes. After revenge had been taken, it was self-preservation for Sam and his brother that became a priority next and the last motivator was set aside until it was nearly erased. But nothing could let Sam completely forget about the one woman he loved in his life, at least not for long.
"Hello Sam," Castiel's habit of appearing in locked motel rooms did nothing to startle Sam anymore, it was a regular occurrence. "I am looking for Dean."
"He's not here Cas." Sam informed him as he went about busying himself with emptying out the rest of his wallet.
"When do you expect his return?" Castiel asked, stiffly standing in the middle of the room. When Sam did not immediately respond Castiel repeated the question. But the Winchester was not listening, his attention was drawn back to the artifacts lain out in front of him, specifically to a delicate piece of jewelry. It was a small ring made up of a thin silver band and a undersized, single stone set in it. It was small enough that it had fit into the depths of leather without a tell of its presence, Sam had completely forgotten it was there at all. If he thought back hard enough he could remember purchasing the ring, and his intention of proposing, but it seemed so long ago that Sam was not sure if it was a creation of his imagination.
"Sam?" Castiel asked. "When will Dean be back? It is important I speak with him."
"Sorry Cas, I couldn't tell you for sure." Sam tore his attention away from the ring and toward the angel. "By the way the waitress was flirting with him back at the diner I wouldn't be surprised if he was gone for a few more hours."
"After intercourse." Castiel said easily.
"Uh…yeah, sure."
"He seems to do that a lot." Castiel observed aloud.
"Tell me about it." Sam mumbled. Castiel finally abandoned the spot he had appeared in and pulled out a chair across the table where Sam sat.
"What is that you are holding?" He asked, eyeing what Sam held in his hand.
"It's just a ring." Sam said without looking up.
"An offering to present to your intended." Castiel said.
"Something like that."
"Who is it you intend to offer your loyalty too?"
"No one," Sam grunted. "There's no one anymore."
"What happened?" Castiel continued to interrogate him. Sam thought for a moment about the question, it was simple enough, but he was tempted to answer with the habitual brush off and subject change. Then he felt a sudden need to answer honestly, to dig up all of the feelings he had buried deep inside of him, to insure that they were still capable of being felt.
"Her name was Jessica, we lived together while I was away at Stanford." He began evenly. "While I was away with Dean on a hunt she was attacked by the yellow-eyed demon, when I got back home I found her on the ceiling of the bedroom just before the entire room burst into flames. She died."
"And you were going to proposition this Jessica?"
"It would seem so, I think I carried around this ring in my pocket for weeks, waiting for the right time to propose to her." Sam said, twirling the silver in his large fingers. "I guess I waited too long."