Sam and Eileen got married. Dean approved. And they all lived happily ever after. The end.
Eileen Leahy - Sam's final love (Season 15)
That is until Chuck wiped everyone from existence (“Despair”).
It's never outright stated that Eileen is the one with whom Sam finds his happily ever after — probably due to the filming restrictions brought on by the coronavirus pandemic — but the implication is there. It's all up to the fans.
After Dean died in the series finale, Sam went on to get married and have a child, whom he named after his brother.
Sam begs for Dean to stay with him and let him work to bring him back to life but Dean asks Sam to let him go. Crying, they confess how much they love and care about each other before Dean dies. We then see Sam start a family with a mystery woman (fans think it's Eileen). Together they have a son called Dean.
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.
Supernatural Season 13 has added a new cast member whose surname will be abundantly familiar to fans. Danneel Ackles, an actress who, of course, is the wife of Dean Winchester himself, Jensen Ackles, is set to play a recurring character.
“Goodbye, Sam” are Dean's final words as his hand drops and a tear rolls down his cheek.
In the end, Dean (Jensen Ackles) went out the way he always thought he would: Hunting. He was killed in the series finale while taking on a nest of vampires, but his ultimate end would come in the show's final moments, when he was reunited with Sam (Jared Padalecki) in heaven.
While it was nice to see Sam (Jared Padalecki) and Dean (Jensen Ackles) reunite in Heaven after a heartfelt Kansas-turned-Neoni rendition of the series' official/unofficial theme song "Carry On Wayward Son," it's no secret that not everyone was particularly happy with the show's ultimate conclusion.
In the series finale, after Dean dies, Sam leaves the bunker behind for good, taking their dog, Miracle, with him. Over the years, Sam has a family and a son, whom he named after his brother, grows old and dies of natural causes. After Sam's death, he and Dean are reunited in Heaven.
Despite this, Sam still had feelings for her and rushed back to her when Dean tricked him into thinking she was in trouble. This strained his relationship with Dean (which was, as always, fixed some time later), but he was reunited with Amelia and had sex with her.
Emma Winchester is the daughter of Dean Winchester and Lydia.
In Carry On, after the death of his older brother, Sam began to live a normal life, while continuing to hunt. In an unknown period of time he developed a relationship with an unknown woman. After some time they had a son, whom they named after his late uncle.
Fitting: He Somewhat Remained A Hunter
Though it is unclear the extent of his hunter life after his brother's death, one of the final scenes shows his son inked with an anti-possession tattoo. This may likely imply that he taught his son some hunting, keeping the family business somewhat alive.
Sam is pregnant with Dean's triplet sons. Although he is only 7 months his belly looks like he is about to pop. Sam has a hard time moving around with the weight in his belly and is almost stuck in the bed till he gives birth.
This is reconfirmed in the Supernatural finale when Sam's soul ascended into Heaven and materialized next to Dean's soul, making him the first person he interacted with in the afterlife. The brothers are unique in that they are the only soulmates who are family rather than spouses.
A Lackluster Plot
Supernatural boldly chose to forego the usual TV finale format - virtually every plot thread was already tied off in the penultimate episode, leaving one final hour to focus entirely on Sam and Dean Winchester. In theory, this made sense.
Dean later briefly possessed a pair of Black Eyes while he was a Demon. Since separating from Sam, his appearance has become more scruffy and unshaven; his hair has also grown out a bit. In Let the Good Times Roll, Dean gains a pair of Angel's Wings due to his status as Apocalypse World Michael's current vessel.
"I cared about the whole world because of you. You changed me, Dean,” Cas added, before saying "I love you," and achieving his moment of happiness, thus ushering in The Empty to absorb both himself and Billie, sparing Dean's life in the process.
After all, despite his intentions, Sam did the unthinkable. He betrayed him for a demon. Dean tried to see past it and focus on task but the hurt was too deep and the betrayal too raw. He couldn't forgive.
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.
Character Information
Millicent "Millie" Winchester is the second child of John Winchester and Mary Campbell, the younger sister of Dean Winchester, and the older sister of Sam Winchester. She is named after John's mother, Millie Winchester. She is the mother of Maury Winchester (Nobah Dee).
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.
On multiple occasions, Dean has shown that - of all the women he has slept with - he truly loves Lisa. Before and during the first few episodes of, season 6, Dean lives with the Braedens for a full year, living an "Apple Pie" life. Dean's nickname for Lisa is "Lis'".