Dean's life has always been in shades of gray. There were times when he was holding Sam, or loving Sam, or raising Sam that he daydreamed about seeing colors that books tried to described. But those few daydreams were overshadowed by the reality of his father's drunken grieving. By the thrown bottles and pain filled cries of a man who saw love and lost it. That is what Dean feared more than the monsters he helped hunt. Sam, in typical Sam fashion, craved it like he craved everything the Winchester boys couldn't afford to have. Which means, like anything with Sam, Dean tried his damnedest to give it to Sam or at least give him a chance of having it. It's one of the reasons that he ignored the college letters Sam received toward the end. It's why he squirreled away money to slip into Sam's bag. Sam was his child, though Dean never consciously thought of him that way. He raised his little brother, taught him everything he could and he believed in the saying 'if you love them, let them go.'

So he let Sam go. Weathered the resulting anger and disappointment from their father with a secret grin. Sam was going to go places. And just because he let Sam go didn't mean he didn't still keep an eye on him. Dean spent too long looking after Sam to just stop. This is how he knew that his little brother had a girlfriend. A girlfriend and loads of friends. The normal life Sam craved so desperately. That's what really kept Dean away the longest though he often wanted to drag Sam home with him. But life has a nasty habit of screwing Winchesters over, which is why nearly two years later he breaks into his brother's apartment. It's a bit creepy, he knows, to be slipping around like this but it isn't his fault! Sam wouldn't answer the phone if he knew the call was from Dean even if the phone bit him. So he's not surprised that he ends up wrestling with Sam.

"You're out of practice," he teases when he pins Sam to the ground. There is a joke about going soft in old age on the tip of his tongue but Sam… Sam is staring at him like he's the best thing in the world or a stranger that is beyond interesting.

"Sam?"

"You've got green eyes like mom."

It knocks the air out of his lungs. Sam can see colors. Sam has a soulmate, one that he obviously loves. Dean sees them standing together, Sam with his arm around her waist possessively and she has a possessive hold on his arm, and knows that he can't do what he came to do. It's too dangerous, he doesn't want what happened to Dad to happen to either of them. Plus he doubts that Sam has told the bombshell, and holy hell if this is how she looks in grayscale what will she look like in HD, about the things that go bump in the night. So Dean turns on his charm, flirting is second nature to him by now, and hopes it will be enough to keep Sam from meaning any yes's he says. He knows better than to try and make it seem like he doesn't want Sam's help though so he ribs Sam into coming down to the Impala to listen to a message he got from their dad. While they go down Dean gets Sam talking about his life. Pride swells in him at the fact that his brother plans on going to law school! Law school! His baby brother a lawyer! They listen to the tape and Dean admits that he doesn't want to do this alone. He hates hunting on his own but he will. He will for Sam to have his white picket fence.

"I'll help you with this but I have to be back by Monday. I mean it Dean, Monday."

Dean doesn't beat his head against his Baby, regretting taking him down here at the stubborn set to Sam's voice, but it's a close call. With a mix of feelings he agrees to the time limit.

It's nice hunting with Sam again. Even with the arguments and the low blows. Even with the evil spirit and getting arrested. He loves it and almost regrets taking Sam home. Dean has never viewed home as a place but the people that inhabits the place. Sam and Dad that was his home and Baby, even though she isn't really a person she feels close enough to one for him, is his home. But to Sam that apartment is Sam's home, Jess is too probably. So Dean takes Sam home to her.

"You know," he speaks at the last moment, watching Sam walk away from him, "we made a hell of a team back there."

It's probably the closest he can get to begging Sam to let him back in his life, for Sam to invite him up, to invite him to call, for Sam to say anything, something that means Sam wants him there. Because they both know that this is Sam's last hunt, that he didn't mean what he said before. Sam smiles sadly.

"Yeah."

Dean takes it as a 'don't be a stranger' and drives off. He hasn't gone far when something in his gut tells him to go back, something is wrong. It's never been wrong before so he goes back. He goes back and hates himself for not being quicker. Because it's a thing from a nightmare, a memory, that is waiting for him when he gets there. He can't save Jess, just like he couldn't save his mom, but he can save Sam so he does. The parallels between the two nights will haunt him, but he pushes past it and drags Sam out. The mantra of Jess that slip out of Sam's mouth with every labored breath and the later pleads for the colors to stay. Please god not Jess, not the colors. Let them stay because if they stay she's okay. Let her be okay. Hurts like gunshots, like knife slashes and creatures claws. It's worse than the time dad would hug him whispering that there were times when he looked at Dean he saw Mary instead. It hurts worse than the times his girlfriends told him they could see colors but it wasn't because of him. There isn't much Dean can do while the firefighters put out the fire that has eaten everything Sam care for. But he tries, he grabs his brother and rocks him, not letting Sam see anything and sings Hey Jude under his breath. And just like that he's back in a dusty hotel that dad left them in worrying about food and knowing that Sam comes first because Sam is his to care for.

Dean isn't surprised that Sam wants to hunt the Demon down after the funeral. Isn't surprised at the mood swings that plague the younger Winchester. Sam is more like their father than he likes to admit.

"We'll get it Sam. We will," Dean promises later as he watches Sam sleep. He'll do anything to make up for letting Jess die, for the colors he has never seen, be stolen from his brother. Even if it kills him.