The first time Dean wakes up after the accident he's alone. There are no nurses, no family, and no friends. He lies there, in pain, with his arm in a cast, silently asking God why He hates him so much. He doesn't get an answer. Silently, he cries because his parents are gone and he wonders how long until everyone else he cares about drops dead as well. His head lolls to the side and he sees his mother's angel statue. It's small and insignificant, with far too many pastel colors, but Dean cries all over again because the pain is still there. Only now it's doubled. He knows he'll sleep better with the angel there, but he also wants to chuck the offending thing across the room.
The second time he wakes up, Sam is right by his bed, Adam is a little farther away from Dean, and he can hear Bobby talking to the doctor in the hall way. His family is here and all he can do is smile weakly at Sam. His big-little brother is blubbering about how he was so afraid he'd lost Dean and how sorry he is. He never should have let them go. The first word out of his mouth is 'Bitch'. Sam cracks a smile, laughing despite the situation and calls back with a 'Jerk'. Dean can't help but think Adam feels a little left out so he grabs the baby Winchester and they have a group hug. They're all sworn to secrecy because Winchesters don't do chick flick moments. Bobby barges in, eyes wet but not crying, and yell at Dean about how grounded he is and asks if Dean has any idea what he put them all through.
Dean leaves the hospital three days later with a neon orange cast on his arm (Ash had visited him while he'd been unconscious) and black Sharpie'd toe nails (Jo got revenge on the make-up fiasco of fourth grade). Dean was more than happy to leave the hospital and go home. It's not even three days after that, that their small makeshift family is attending John Winchesters funeral. Dean knows he has a big family who loves him, but right there, standing in front of his parents-laid to rest side by side-he can't help but feel so alone. Like the world is trying to drown him in sorrow. He can't help but be bitter towards God for forcing him to live without his parents.
But then again, he's not really parentless. Bobby is his surrogate father; he teaches him everything he can about cars when he can, he taught all of them self-defense, and how to handle guns. Ellen, even though she could never replace Mary, is the best maternal figure Dean has; she taught the boys how to mix drinks, gave them their first bit of alcohol, and-secretly because none of his friends can know-she's teaching Dean all of her recipes and his mother's old recipes. And even without parents, his family is so big.
Dean's life returns somewhat to normal. He goes to school, people spread rumors about his broken arm-
'He got it in a gang fight on his turf!'
'The mafia got him cause he owed money!'
'He got it fighting a dinosaur in space, while simultaneously fending off a comet that was going to destroy the world!'
-yeah that last one was Garth, but Dean wasn't going to ruin his fun no matter how ridiculous he got. He still went to school, he still had some trouble, he still went to the park every day after school.
It's not even two weeks after things go back to normal when things twist again. Dean considers himself a pretty open guy. He accepts people for who they are not what they do. So he only has one problem when he finds out that his uncle is seeing a guy; Dean saw everything. And he meant everything. On the kitchen table. In the middle of the afternoon. On a weekend. Needless to say, the Winchester boys spent the night in the 'Children of Letters' hideout that night, getting drunk and acting stupid. That was how the boys got introduced to Crowley McLeod, business man and longtime boyfriend of Bobby Singer. None of the boys care when they're sat down for the discussion. The only thing they request from their uncle; keep it in their bedroom!
It happens one day out of the blue. Dean comes home directly after school one day and heads to bed. Sam and Jo are left at the park waiting, but when no one at all shows, they go home. It doesn't happen again for another three weeks. But this time he doesn't go to sleep, he lounges around in the living room. It happens again nine days later; he comes home and asks Bobby to work on his father's Impala. Eventually, Dean stops going to the park at all. He comes home, does his homework, and works on the Impala. At first Bobby is worried, but Dean's therapist says it's a good thing that Dean is finally moving on.
Dean no longer holds his memories close. He tells all of his other friends about him and the Park. They all even go there one day together and goof off. But after that day, Dean makes a silent vow to himself to never go back to that park again. He can't spend the rest of his life waiting for his old best friend. He spends all of his time hanging out with his friends who are getting older, but none of them are capable of growing up. He works on his father's car in his spare time, and it's finished by Summer break. When Dean goes to give Bobby the keys, Bobby just hands them back.
It was John's car, so it should go to Dean. Dean things that his summer just got infinitely better. Their group of friends decide to go to the lake. Dean drives his Impala, with Sam as his shotgun and Charlie and Jo are in the back. Ash is driving his pick-up with Garth and Adam. Sam's friends Jess and Ruby are driving in Jess' little beetle. They go to the lake, and they have the best time that they've had in a very long time. For that day, no one is missing. No one is incomplete. No one is sad.