Season 6. One year later, Dean is still living with Lisa. Dean is now a retired hunter, and has a normal job.
Dean appeared less frequently on Gilmore Girls starting in Season 4, as he eventually married Lindsay. Rory didn't react well to the marriage, and at the end of the season, Dean cheated on his wife with Rory, which resulted in Rory losing her virginity.
Fans get some cute moments between them when Dean drops Cas for his date and gives him some tips. At the end of the season, Cas again has to choose between heaven (this time an angel army) and Dean, and to no one's surprise, he chooses Dean.
History. Dean/Castiel slash fans pair the characters Dean Winchester and Castiel in a romantic and/or sexual relationship. This pairing is most commonly referred to as Destiel.
As Sam prepares to sacrifice himself to Lucifer to stop the Apocalypse, he urges Dean to seek out Lisa after his death. Dean does this, and lives with Lisa and Ben for a year. He has a monogamous relationship with Lisa, and takes on a paternal role with Ben.
Jared Padalecki proved that he might've never watched an episode of his own damn show in an interview with Variety. And like expected, it caused quite a stir for shippers who know in their hearts that Sam Winchester ended up with Eileen Leahy.
When Dean had first met Ben Dean considered the possibility that Ben might actually be his son. Lisa confirmed to Dean that Ben wasn't his son and his similarities to him was due to her 'type' that she hooked up with that Dean had fallen under.
Emma Winchester is the daughter of Dean Winchester and Lydia. She is an Amazon warrior, trained to kill her father, but she refuse to go through it and was accepted by her family.
Dean Winchester & Robin
However, as a teenager, Dean did find love with a girl named Robin. Like always, Dean didn't get to stay with her but they did have a moment where they reconnected their love even if it was briefly.
The finale took place five years after the penultimate episode, according to Jared Padalecki, placing the timeline in 2025. By this point, Dean would have to be 46-years-old, leaving that as his final age. In Heaven, he met Sam about 25 years after his death, meaning Dean would have been 71 had he lived until then.
Eileen Leahy - Sam's final love (Season 15)
But, Sam managed to turn her ghost into flesh, bringing her back to life (“Golden Time”). The two of them developed a romance that culminated in Season 15.
However, his affection for Castiel ultimately won, with Dean shown in tears in Purgatory when he thought he'd lost Castiel. Their reunion was their most intimate yet, as the two didn't hold back on letting the other know that they were truly sorry and didn't want to fight anymore.
In Supernatural's series finale, Dean Winchester died on a hunting job, but his soul eventually ended in Heaven. Some fans were happy to see a proper conclusion for Dean Winchester's story, while others argued that he deserved better.
Rory losing her virginity to Dean at the end of Season 4 seemed like a pretty positive experience—except that, y'know, he was married at the time. But Rory's so oblivious to her own wrongdoing that she doesn't actually seem all that upset by the whole thing, so this probably qualifies as the best of the three.
Throughout the second season, Jo appears to have romantic feelings for Dean, but Dean does not have feelings for her, it seems to him that she is like a sister to him.
Not only does Dean die on a routine vampire hunt, passing away slowly in his brother's arms (which coincidentally may be the best scene in the entire final season), but he's briskly whisked away into Heaven solo.
His final sacrifice (Season 15, Episode 18)
In order to save Dean's life, Castiel called upon his deal with the Empty. Realizing that true happiness could be achieved by speaking his truth, he told Dean that he loved him.
Out of Castiel's three lovers, Meg and April, Daphne is the only one with whom Castiel had a successful relationship, as Meg was killed approximately a year later and April was a reaper tasked with killing him. It is unclear if Castiel remembers Daphne, or whether he cares about her at all.
Finally apologizing, Sam tells his brother, “I should've looked for you when you were in purgatory.” Sam never forgave himself for that. But Dean's forgiven him.
Cassandra Masters is the daughter of Castiel and Meg Masters and the only known Nephalem to exist, which is a hybrid between a union of an angel and demon, even being part human due of Castiel and Meg's human vessels. Cassandra acts as one of the leading main characters with Sam and Dean.
Lydia met Dean Winchester, along with Castiel at a bar. She shared a conversation with the Winchester and then went to her house where the two enjoyed a night together. Unknown to Dean, Lydia was impregnated with his child and in just a couple of hours, Lydia was already nine months pregnant.
This leads us to believe she already knew she was pregnant and trying to decide what she should do. Rory also doesn't drink the coffee Christopher hands her, and we know how much the Gilmore girls love their coffee. To that end, Logan is most likely the father of Rory's baby.
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.
Adam Millagan is a supporting character in Supernatural. He is the younger half-brother of Sam and Dean Winchester and the son of John Winchester. He appears as a minor character in season 4 and a supporting character in seasons 5 and 15. He also serves as the primary vessel for the Archangel Michael.
Due to Jack being the son of Lucifer, Dean originally viewed Jack as a threat that had to be stopped from being born. After Jack was born, with Sam unwilling to kill him, Dean would keep an eye on Jack, threatening to kill him if Jack ever turned evil. Jack in turn sought Dean's approval and affection.