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DEAN WINCHESTER
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Shapeshifters take Manhattan! The Winchesters meet Beverly Rogan.
During a run-in with the Thule, Dean kills Hitler.
The events of IT: Chapter Two. The Losers defeat Pennywise; Eddie is hospitalized. Beverly reconnects with Dean, reverting back to her maiden name Marsh.
Sam and Dean are taken into custody by the Secret Service after attempting to eject Lucifer from the President's body.
Sam and Dean are held in solitary confinement at a government blacksite for two months. They're McFuckin Pissed when they get out.
Dean gets fucked up on a solo hunt. Beverly comes to his aid.
Crowley sacrifices himself to close the rift to Apocalypse World; Lucifer kills Castiel. Mary and Lucifer are trapped in Apocalypse World as the rift closes. Jack is born.
Dean tries to break it off with Beverly. It doesn't go quite as planned.
Bev's first ghost hunt while the boys are stuck in the Bad Place. Dean calls her in the aftermath and things get a little spicy.
Dean shows up at Bev's place with Depression Beard TM from weeks of rage hunting after his failed mission to bring Mary and Jack back from Apocalypse World. Beverly invites Sam to New York for the holidays.
Christmas brunch with Sam.
New Year's Eve party at Ben's place in Long Island. The Winchesters finally meet the entire Losers Club. Dean and Bev share a New Year's kiss.
The Winchesters mount a rescue operation and spend roughly a week in Apocalypse World reuniting with Mary and Jack. They return home with their family as well as Apocalypse World refugees, but Michael and Lucifer are hot on their trail. In order to finally destroy Lucifer, Dean says Yes to Michael.