After almost fifteen years, Supernatural has covered a range of themes from found family to heroism to good versus evil. Although romance has never been a central aspect of the show’s narrative, it has produced a number of significant couplings that have accented the story.
For better or worse, these relationships have revealed layers to the characters that fans know and love. Showing that characters who can save the world also value love make them more understandable as people. Whether they meshed well, fell flat, or were downright toxic, the relationships built in the show have played an integral part of the story. Here we take a look at their length as we rank them.
10 Sam & Ruby: 2 years
It may be controversial to call this pair a couple, but the two definitely had strong feelings for each other, even if they were helped along by demon blood and an impending apocalypse. Ruby saves Sam from a demon attack in season three long before revealing that she is a demon herself. Slowly, though, she gains his trust, and by season four, they have developed a sexual relationship.
Despite warnings from Dean and Bobby, Sam continues under Ruby’s guidance throughout the year, drinking her blood, until he is able to kill the demon Lilith. This act, unbeknownst to Sam, would set Lucifer free from Hell. When Ruby reveals that this was her plan all along, she is promptly killed by the Winchester brothers, bringing an end to the relationship.
9 Jody & Bobby: 1 day
Some fans may not remember this attempt at a pairing as it only existed for a brief time in season seven. The two had taken turns saving each other from monsters until the episode “Slash Fiction,” where Jody finds Bobby at a cabin outside of town to thank him.
The relationship felt forced considering what we had known about each of the characters at that point in the show. They shared a great friendship before there was anything romantic about it. However, it becomes inconsequential upon Bobby’s death later in the season, and the flame between them will remain a blip in each of their narratives.
8 Mary & Bobby: 2 years
It’s not clear when this relationship started, but this couple presumably built most of their relationship off-screen. The alliance-bordering-on-friendship they shared while leading their group of rebels in the apocalypse world was sweet and a big part of both their season thirteen stories, but once Sam comments on their romantic relationship in the next season’s “Nightmare Logic,” their whole dynamic starts to feel uncomfortable.
The couple decides to hole up in Donna’s cabin for a while, which doesn’t last long before Bobby leaves. Mary is killed before we ever see them together on screen again, putting a perhaps redundant ending to their romance.
7 Sam & Jess: 18 months
From the beginning of the show, Jess joins the countless women in the world of fiction who have fallen victim to the “girlfriend” role; that is, we know that she was Sam’s love interest and nothing else about her. As she was killed in the pilot, this is likely all that will be revealed about her, so it’s difficult to judge the chemistry between them.
Despite this, and despite the fact that their coupling was planned by the demon Azazel, most fans agree that she is the love of Sam’s life. In the early seasons, allusions are made to his intentions to propose to her, after they had been together for a year and a half. It seems safe to assume that the couple was strong until Jess’ demise.
6 Hannah & Castiel: 1 year
This pair gets off to a rocky start, with her trying to kill him upon their first meeting near the end of season nine, but the two angels have shared experiences and values that make them compatible and differences that make them interesting together.
They ally themselves with each other in the war against Metatron and succeed against the odds. Their conversations offer insight into the conflict of angelkind versus humanity. They have both experienced guilt of stealing their vessels’ lives, and in the season 10 episode “Girls, Girls, Girls,” Hannah chooses to leave her vessel and return to Heaven. The relationship ends on a sour note when he kills her, but their story changed both of their perspectives on the world.
5 Sam & Amelia: 1 year
After Dean disappears at the end of season seven, Sam travels to Texas, where he hits a dog and meets Amelia, a veterinarian. Both are going through hard times — Sam had just lost his brother, and Amelia had lost her husband. They bond over their losses and grow to love each other. Their love wasn’t intense and all-consuming, but they made each other happy.
After spending a year together, Amelia learns that her husband is alive while Sam learns that Dean has also returned. In the end, Sam chooses life on the road with his brother instead of a simple life with her. The show’s writers, actors, and fans have voiced strong opinions about this pairing, but there is no doubt that the two were in love and wanted what was best for each other.
4 Dean & Cassie: 2 weeks
Cassie is often regarded by fans as Dean’s first love. He boasts many sexual conquests, but Cassie, who appears in season one’s “Route 666,” is the first woman who proves to be more than a fling for him. They met before the start of the show when Dean stayed in her town working a case with his father for a couple of weeks, and he trusted her enough to keep the secret of what his family does.
“You loved her,” Sam observes after seeing the two together. Later in the episode, it’s revealed that Cassie had called it off, and Dean hit the road again. When a case brings him back into town, they spend a passionate night together before sharing a tender goodbye and parting ways.
3 Dean & Lisa: 1 year
Lisa was undisputedly Dean’s longest love. She started as simply a “bendy weekend” for him before she was introduced in season three, but a glimpse into Dean’s dreamscape in the episode “Dream a Little Dream of Me” reveals that he envisions himself being with her in a perfect world. After Sam plans to jump into the Cage with Lucifer, Dean finds Lisa and starts a new life with her and her son, Ben, until Sam returns a year later.
To Dean, Lisa represents a nice, normal life where he doesn’t need to hunt, and their relationship gave her what she wanted more than anything: a father figure for Ben. Upon Sam’s return, Dean chooses his brother over his newfound family, and Castiel wipes him from their memories, marking an end to their love story.
2 Meg & Castiel: 3 years
This pair may consist of an angel and a demon, but they are each able to bring out the humanity in each other. They first meet in season five, each fighting on opposite sides of the apocalypse. Neither is able to defeat the other, but they cross paths later, their causes aligned this time, and join forces.
When Castiel is rendered unconscious for months, Meg poses as a nurse to look after him, and when she is captured and tortured by Crowley, Castiel rescues and cares for her in the season eight episode “Goodbye Stranger.” Her death in the same episode ends their on-and-off relationship, but these two added dimension to the show, bringing to life the idea of what’s good and what’s evil.
1 John & Mary: 47 years
None of the events of this show would have been possible without the love shared by Mary and John Winchester. Their relationship was quite literally a match made in Heaven when they met outside a movie theater in 1972. Their time together comes to an abrupt — but not final — end when Mary’s death kicks off the series, but in time travel episodes, it’s clear how much they love each other.
The couple reunites in “Lebanon,” though this reunion is also brought to a close within the episode. Since what seems to be her final death in the season fourteen episode “Game Night,” they are currently together in a Heaven designed just for them. Their relationship has truly withstood the test of time, of life, and of death.
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