As they talk, Bobby mentions
Jack says he snapped and it was over quickly. He wishes it didn't happen. Dean is barely holding it together. He doesn't like that Jack is calling Mary's death, “the accident.” But he plays along and says they understand and they forgive Jack.
Before he leaves, he gives Dean a hint, and tells Dean to keeping digging because they're getting close to the truth.
However, after reuniting with Dean, things begin to change as Dean discovered after capturing the Alpha Vampire that he was working with Crowley. Because of that, he didn't get along with Dean. During one mission, Samuel later sold his grandsons out to Crowley which forever ruined his relationship with his grandsons.
Dean killed Benny, returning him to Purgatory where he led Sam and Bobby out but remained behind to cover their escape. Dean returns from Purgatory carrying Benny's soul in his arm and travels to Benny's grave in Louisiana. There, Dean performs a ritual, restoring Benny's soul to his body and resurrecting him.
We know from the exchange in 8x05 that Dean didn't even trust Benny in purgatory until Benny saved Cas's life. It was that act that made Dean change his mind and actually grow fond of Benny to begin with. So Dean's feelings for Benny are BECAUSE of Dean's feelings for Cas.
Regarding the time which purgatory lasts, the accepted opinion of R. Akiba is twelve months; according to R. Johanan b. Nuri, it is only forty-nine days.
Before dying, John tells Dean, if he can't save Sam, he'll have to kill him, should he become evil. The fourth season episode "On the Head of a Pin" reveals that the demon Alastair tortured John in Hell for over a century, with John refusing the demon's offer to stop if he himself would torture someone else.
Dean wasn't just angry for Castiel's role in bringing the worst out of God, as his main anger came from the idea that Castiel was responsible for the death of Mary. Making things worse was when Castiel killed the traitor Belphagor, which led to Rowena having to sacrifice herself.
Dean, though, had no plans to forgive Sam or even hear him out. Dean decided he didn't want to stick around the brother who was being shunned by the rest of the world and abandoned Sam. Dean didn't even consider how he was the first one to break Lucifer's seals and Sam didn't hold it against him back then.
After years of sacrificing himself for his family, it felt sort of anticlimactic when Dean died by accident in the field. Rather than some macho-heroic death or some world-ending mission (he'd been on plenty of those before, and even died in a few), Dean was impaled while fighting a masked vampire.
Season Eight begins with Dean Winchester returning from purgatory, where he was sent after defeating the leader of the Leviathan – ancient monsters and first residents of purgatory. Dean spent a year in purgatory before being able to escape with the help of his vampire friend, Benny, whom he met in purgatory.
But once confronted with the deal, Death was less interested in getting his ring (because he claimed to know where Dean had hidden it) and more interested in getting Dean to walk in his shoes. So he made him a deal: If Dean could be death for 24 hours, Sam would get his soul back.
Finding that she has been gone for thirty-three years, Mary finally believes that Dean is her son and the two embrace. As the morning came, Dean and Mary say on park bench, with tears in her eyes, Dean begins telling her about John and how he sacrificed his life for Dean and raised he and Sam to be hunters.
Emma was an Amazon conceived by Lydia and Dean during a one-night stand, unbeknownst to the latter. After trying to kill Dean, Sam shot her, killing her instantly.
Jack uses his powers to heal Cas because the antidote obtained via the best plan of all time unfortunately doesn't work. When he tries to also heal Dean, though, Cas won't let him; he's confident Dean will heal (because he's Dean, and Dean is Dean) and Jack is being entirely too cavalier about his soul.
Misha Collins has opened up about Destiel being canon and how their storyline plays out in Supernatural season 15. Destiel shippers assemble. Misha Collins has confirmed that Castiel was "homosexually in love" with Dean in Supernatural.
Immortality – Castiel, as an angel, like all celestial beings, doesn't age over time and is immune to disease. He never tires, and does not need to eat, sleep, drink, or breathe to sustain himself or even his vessel.
Supernatural season 15 controversially saw Castiel declare his love for Dean Winchester before dying.
Like A Virgin is the 12th episode of Season 6.
Power: Dean
Even if Sam is taller and generally seems more fit, Dean has demonstrated on many occasions that he's the more powerful of the Winchester brothers. No matter if it's a fistfight, a weapons-laden war or simply leveraging his weaknesses against an opponent's, Dean is the better brother.
Dean tells Lisa "you knew what you signed up for". Lisa replies, "I did, but I didn't expect Sam to come back". She knew their relationship was "over the moment Sam walked in the door", and tells Dean how weird his and Sam's relationship is. With Sam, Dean can never be happy.
Time is warped in Purgatory; a minute in the real world corresponds to a year in Purgatory. It is basically a universe separated from the mortal plane.
According to the writings and visions of countless saints and theologians, most people who die in a state of grace are not yet fully purified. Their souls are not ready to see God face-to-face or to embrace perfect union with Him.
The person would go straight to Heaven, bypassing Purgatory, if, and only if, that person's heart was ALSO perfectly open to the infinite grace given through this indulgence. Forgiveness of sin is certain. Therefore, Heaven will happen.