>>3509059In the beginning of the episode the boys seem happy and fine after everything that's happened. Dean has apparently replaced Cas with a dog. Sam says that he thinks about Cas sometimes and how he sacrificed himself, and Dean just kind of brushes it off. Episode starts as a generic motw, and they work a vamp case. We see that Dean has Cas' coat in his trunk, but without the narrative weight of it being the only thing of him that remained in S7 it just feels like hollow fanservice, and it's not even folded.
A rando vamp from S1 makes a pointless cameo (note that Castiel does not make an appearance in this episode, but this generic bitch nobody remembers does), they fight, and Dean gets skewered on some rebar and dies after giving Sam a tearful speech about how proud he is of him. Sam then burns his body and moves on with his life.
We see Dean go to heaven and meet Bobby, who tells him that heaven is shared now and he can go visit his terrible parents whenever he likes. Jack changed the rules with the help of Cas, who has apparently been back this whole time, is still very much an angel, and never met up with the Winchesters again. Dean barely acknowledges that. He looks up to see Baby and decides the thing he wants to do most now that he can do anything imaginable is drive his car.
While Dean is driving we cut back to Sam, who quits the life, marries a women who is not Eileen (she also gets no mention this episode), has a son named Dean, grows old, puts on a bald cap, and dies in a bed. Cut back to Dean, still driving. He pulls over on a nice bridge, and there is Sam, young again now that he's in heaven. They hug. Nobody else appears. End episode.
Dean never got to live his own life. Cas has never been told that he is loved. And Sam loses his entire family. But at least now they can enjoy an eternity of character regression. The end.