Dean has always been in good shape. Doing what they did and having an ex-Marine for a dad wouldn't allow for anything else. But he'd never actually worked out or anything. Sure, the old man would make him or Sammy drop and give him twenty (or fifty, depending on the severity of their indiscretions) when they got out of line but other than that? No real regimen.
Until Sam leaves for Stanford.
The night that Sam slams out of their suddenly too small one bedroom efficiency, Dena leaves. Just walks out with no destination in mind. John is already passed out in the bedroom, Jim, Jack and Johnny there to watch over him. Dean grabs his leather coat and his wallet and just leaves. Forgets until he reaches the parking lot that the Impala is at the garage of one of John's friends getting a new front fender and carburetor.
It's all suddenly too much and he just starts running. He realizes three miles later, hot, feet burning, that he doesn't recognize the street he's on and that running like that was not the best idea he'd ever had. He walks three blocks before finding a bar and takes a page from his old man's book, getting shit faced.
His dad takes off for New Mexico two tense days later and Dean is at loose ends. He was left with neither coordinates or instructions. He spends the first day cooped up in the room, eating stale Cheetos and watching day time television.
The next day, he's awake at five. Does one hundred push ups and then one hundred sit ups before six. He thinks about going running again then remembers the blisters still on his feet. He manages to wait until ten then makes a trip to the local mall. He purchases a pair of running shoes, some athletic socks and a pair of black nylon shorts, courtesy of one Tim Lowry's Visa card.
He will never admit to owning or wearing that last item. Ever. Not even if Sammy-
He cuts his train of thought short and exits the store as quickly as possible.
The next morning he's sore as hell and does nothing but drink and pop some pain relievers he found in his ancient first aid kit.
By the time he meets up with his dad again, he is up to running ten miles daily and two hundred of both push ups and sit ups daily. If his father notices his new early morning habits, he doesn't mention them.
He is in the best shape of his life physically and looks forward to that blissful time each morning when the only things filling his head are the rhythmic thuds of his feet hitting the asphalt and his breathing. For once his head isn't full of the emptiness of Sam not being there, of not knowing if his little brother is safe, of wondering when Dad's gonna go off and not come back. Of when it'll just be him.
He runs in solitude to escape his fear of being alone.
The irony is not lost on him. He smirks, knowing Sammy would be shocked he knew what the hell irony even meant, let alone that he could use it in a sentence.
He keeps the regimen up, running, pushing his physical limits and then suddenly. His dad disappears and he finds himself in Palo Alto asking Sam for help.
Dean's grateful of his endurance, first when that Constance bitch tries to run him down with his own damn car, then again when she kidnaps Sam in the Impala.
As he runs the seven miles to the Welch farm, in his boots for fucks sake, he thinks he really needs to amp up the protection spells on his baby or maybe get the Impala blessed again. This was getting ridiculous.
He's still not sure what makes him go back to Sam's place after dropping him off. Doesn't know what he would've said to him anyways. He's Dean Winchester, not like he can come out and say, 'I miss you,' or 'I don't wanna be alone anymore.'
All of what he couldn't or wouldn't say becomes a moot point once he sees the flames flickering inside Sam's place. He pulls his brother out of another fire as another woman who loved Sam perishes in it.
After that, Dean's sneakers stay relegated to the bottom of his duffel.
The shorts are thrown out on their way to Colorado. Sammy'd never let him live those down.