Today is Dean Winchester's birthday. I'd like to think he was celebrating it in the bunker with Sam and Miracle. It's a little unclear in canon when the vamp hunt that ended his life actually went down. Some think it was their first hunt after defeating Chuck since the episode didn't show anything besides a normal morning in the bunker. I prefer to believe that he died a few months later, giving enough time for the brothers to drive the back roads together that we saw in the montage at the end of 15.19; a chance for the brothers to get back to hunting together without the threat of Chuck and his manipulations.
After all, the final episode went ahead in time to show us Sam as an old man with a grown-up son so, if time passed then, why couldn't there have also been a passing of time before Dean met up with the rebar in that barn?
But, whatever the amount of time was, the fact remains that it is January 24, 2021, and Dean Winchester is not here. He always said he'd die young, and 41 is a lot better than 28, but it is still too young for those of us who loved him. It makes me sad to think that the Winchester brothers aren't driving together in the Impala across the United States, hunting down monsters and saving people.
However, Dean surely deserves the rest: "there'll be peace when you are done." Early on, Dean admitted how tired he was of the emotional strain of the job, of the pain of losing those he loved and the constant anxiety of the potential imminent death of his remaining family. "I'm tired, Sam. I'm tired of this job, this life . . . this weight on my shoulders, man. I'm tired of it." (Croatoan, 2.09) And that was even before they knew about the Apocalypse, their destiny as vessels, and then Chuck's machinations.
Dean's life was one of constant sacrifice and loss and grief and pain. He was well-known for being able to snatch joy wherever he could find it -- telenovellas, his music, his Baby, Scooby-Doo, PIE! -- but the overwhelming theme of his life seems to be tragedy. After losing his mom at age four, he never had a stable home. He didn't have a normal childhood, instead moving from school to school, unable to form lasting relationships. He gave up any chance at college or a future outside hunting. He lost his father and his father figure, Bobby; he lost romantic relationships - Cassie and Lisa. He lost Sam more than once (and getting him back again doesn't always wash away the marks a grief like that makes on one's soul). He lost people he wanted to protect like the Harvelles and Charlie and Kevin. He lost his mom a second time at the hands of someone he was beginning to see as a son. He lost friends like Benny, Lee Webb, and, most of all, Castiel. He lost his faith in himself as being a good person (although his family kept trying to reassure him that he was), and he lost any faith he might have secretly had that there was someone greater than humans who was loving and compassionate. Despite that, Dean kept going: "we've got a job to do." "No matter how much it hurts, no matter how hard it gets, you gotta keep grinding" (11.15). Even facing incredible odds, he, buoyed by his brother, kept fighting.
After a lifetime of that, Dean deserves peace. In Heaven, he has finally found endless happiness, even if it's hard for us to picture it. Heaven is nearly impossible to imagine. How does it even work when you're outside time? Does Dean just keep driving the Impala forever? Is he always on back roads and deserted bridges overlooking the wilderness or are there towns and gas stations and diners? Does he hang out at the Roadhouse? Do he and Sam sit down with Mary and John and share a meal?
St. Paul wrote this about Heaven: "Eye hath not seen, nor ear heard, neither have entered into the heart of man, the things which God hath prepared for them that love him" (1 Corinthians 2:9). At the end of the Narnia series, C. S. Lewis wrote, "The things that began to happen after that were so great and beautiful that I cannot write them. And for us this the end of all the stories, and we can most truly say that they all lived happily ever after. But for them it was only the beginning of the real story. All their life in this world and all their adventures in Narnia had only been the cover and the title page: now at last they were beginning Chapter One of the Great Story which no one on Earth has read: which goes on for ever: in which every chapter is better than the one before.” I've always thought that that's the best way to describe Heaven - just hints, nothing definite - because descriptions of Heaven always seem to fall short. It's hard for us to imagine something truly perfect.
I guess that's where faith comes in: faith is believing without seeing, with knowing something is true even without having all the details. So I will imagine Dean, on the 42nd anniversary of his birth, finally completely happy and unburdened, surrounded by those he loves, never having to say goodbye to them again.