Warnings/Spoilers: Major spoilers for season five, especially the finale as this is meant to be a missing scene.
A/N: Thanks to sendintheclowns for being my beta once again. I tweaked it a bit after her hard work so any existing errors are obviously all my fault. Excuse my terrible summary but unfortunately I severely lack in that department.
Summary:
Winchesters don't do goodbyes but Sam's always enjoyed testing the limits.

A Ring and a Promise:

Dean thought they'd said everything they needed to in the car, but he should have known Sam wouldn't be satisfied till he left Dean with a lump in his throat the size of Texas. He knew Sam had been dying to say more the entire drive but it wasn't until they stopped in Davenport that his brother finally got up the nerve.

It seemed a little pointless to get a motel room for a few hours, but they needed rest. If Sam was going to take on the devil then Dean was going to insist he got at least a couple hours of sleep in a bed and not the passenger seat of the Impala. So without even asking he pulled off the highway, got a room and practically dragged Sam inside.

"We shouldn't be wasting time, Dean," Sam argued.

"I told you I'd back you Sam and I am," Dean sighed, "but this whole plan requires you going in one hundred percent. That means you get at least three hours of sleep or the whole thing's off."

"You can't just call off saving the world." Sam rolled his eyes and took a seat on the bed furthest from the door.

Dean smirked as he sat down on the other bed, his knees brushing Sam's. "You don't think I will?" he asked, daring Sam to challenge him.

He expected Sam to shrug or roll his eyes again but instead Sam just stared at him as if he were a specimen being studied under a microscope. It made Dean uncomfortable and caused him to squirm under Sam's gaze until eventually Sam shook himself out of the daze.

"You're going to go see Lisa after all of this, right?" Sam asked, though it sounded more like a statement.

"Sam—"

"I just want to make sure," he cut Dean off quickly, avoiding the obvious argument.

Dean could tell by the way Sam's eyes focused on his folded hands—fingers clenching and unclenching around each other—that his brother still wasn't finished. He knew whatever it was Sam wanted to say couldn't be easy, but saying goodbye and trying to fit everything you need to say into one last conversation wasn't supposed to be a breeze.

Dean wasn't ready to say goodbye yet either. It was hard enough to promise Sam he'd keep on functioning, and finding happiness when it was all over seemed impossible, but he didn't have it in him to deny Sam's last wish.

Finally Sam reached for his backpack and rummaged through it before pulling out a small, black velvet box. He twisted the box around in his hand, running his fingers over it in gentle, reverent strokes. In the last four years of hunting with Sam he'd never seen the box before but it's obviously that it's something very important to his brother. It made Dean wonder why Sam had kept it from him for so long.

"I want you to have this." Sam shoved the box toward Dean.

Dean stared at it for a few seconds before reaching out and taking it from Sam's hand, showing the same gentleness as Sam had. He caught the nervousness on Sam's face as he pulled it open but when he peaked inside the box, everything made even less sense.

"Oh Sam, you shouldn't have," he teased as he inspected the diamond ring nestled between the soft foam keeping it in place.

"I bought it for Jess." He closed his eyes and took a deep breath before looking back up at Dean. "I was kind of hoping you'd give it to Lisa."

Dean stared at him as if he were crazy and quickly slammed the box shut, shoving it back toward Sam. He couldn't do that. It wouldn't be right. That ring was the only piece of Sam's old life that made it out of Stanford. Dean couldn't even believe that Sam had managed to hold onto it for so long.

"I can't," he said softly, nudging the box toward Sam again. "It wouldn't be right."

"I'm asking you to, Dean," Sam replied softly as he pushed at Dean's hand. "This way I know it's in good hands. It'll be something for you and Lisa to remember me by."

"You think a ring can do that?"

"Maybe."

"Sam," Dean took a deep breath and ran a hand over his face. "I don't need anything to help me remember what a pain in the ass you are. It's impossible to forget."

"Then just humor me, man," Sam grabbed the ring back from Dean and popped it open. "I used to stare at this ring every night, trying to convince myself to grow a pair and just ask her. I never got the chance, Dean, but you could. At least this way I'll be a part of it."

It made sense. Dean understood and appreciated the sentiment but he wasn't ready for it yet. Sam had already made him promise to go see Lisa but Dean wasn't about to promise that it would be a permanent thing. He wasn't sure he'd ever be ready for that but if this ring meant that much to Sam then he would hold on to it.

"Okay," he agreed but said nothing more. Apparently it was all Sam needed to hear as Sam looked up with a smile, shoulders relaxed as if Dean has just taken the world from his shoulders after years of carrying the burden.

"Thank you." Sam whispered.

Dean shrugged, "Saves me from trying to pick one out if the time comes."

When Sam laughed, Dean felt his chest tighten. It wasn't all that often that he got to hear that sound but he was pretty certain it'd be one of the things he missed the most. He would never be ready to say goodbye but they have one chance at saving the world and if anyone could do it, Dean knew damn well it would be Sam. Even if Sam were to lose, his little brother had done what no one else would or could have. Sam was the only man brave and stupid enough to take on Lucifer.

The End.