This is going to be unconnected, stand alone one shots.
Title: And I could have spent a life with you, but those days were over.
Spoilers: Dark side of the Moon
Disclaimer: Supernatural isn't mine. Title from Better Than Ezra
Notes: Sam/Jess
She's something he wishes he could forget completely, and yet cherishes the memory of her. A memory that both comforts and burns him at once.
Sometimes when he thinks she's all but faded and he can't even summon up a clear image of her face, his eyes will start to sting and a lump forms in his throat. The guilt is nearly too much. Then there are moments when her face will flash through his mind, clear as if he'd seen her only the day before, and the sound of her laughter will ring in his ears, and the grief is almost more than he can stand. All these years gone by and still it's gotten no easier.
But the thing that cuts him the deepest? The little truth that can all but bring him to his knees? He's seen his heaven and if he ever makes it there again he knows Jess isn't there. Not even a memory of her.