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Supernatural: The 5 Best Couples (And The 5 Worst)

Supernatural isn’t exactly known for its romantic relationships. Still, over 14 seasons, fans have seen their fair share of Supernatural couples.

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Whether it’s Dean, Sam, or Cass trying to live a normal life, romance that blossoms out of the thrill of the hunt, or something else entirely, the show has featured several noteworthy couples. Here, we’ll take a look at some of the best and worst couples from Supernatural.

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Supernatural John and Mary
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10 BEST: JOHN AND MARY

Supernatural John and Mary

The relationship of the Winchester parents, John and Mary, has been so idealized on Supernatural, that it’s hard to know what it was really like. Here’s what we know for sure: Mary was raised to be a hunter but instead of bringing John into that life, she left it all behind. She enjoyed a normal, happy life with John and they had two sons who would go on to save the world.

When Mary died, John’s love for her was so strong that he couldn’t let her death go. He became a hunter and brought his sons into the life specifically to find the demon who killed Mary. Decades later, Sam and Dean still miss their mother and father and would give almost anything to bring them back.

9 WORST: CASTIEL AND DAPHNE

Supernatural Castiel and Daphne

Poor Daphne had no idea who Castiel was when she married him — and neither did Cas. Somehow after seemingly dying, Castiel was brought back. Daphne found him, took him in, and they eventually married. The couple also discovered that Cas, who was going by the name Emmanuel, had the power to heal those in need.

This put him on Dean’s radar, who went to find Emmanuel only to discover it was his angel friend with amnesia. After spending a little time with Dean, Cas’ memories came back in a hurry and Daphne never came up again.

8 BEST: SAM AND AMELIA

Amelia and Sam Supernatural

After Dean ended up in purgatory at the end of Season 7, Sam decided to retire from hunting instead of looking for his brother. In the year that followed, he met and started a life with Amelia. It was exactly what Sam always dreamed of — a normal life, complete with a dog — but when it comes to the Winchester brothers, normal doesn’t last long.

For some reason, with this relationship, the writers decided to throw in a soap opera twist: Amelia’s husband, who she believed had died in Afghanistan, turned up alive. Before Dean returned, Sam had already stepped aside so Amelia could be with her husband.

7 WORST: DEAN AND LISA

Supernatural Dean and Lisa

Dean believed that Lisa could be his one shot at happiness and a normal life. So when Sam decided to trap himself and Lucifer in the cage, he made Dean promise to give up hunting and be with her. Dean makes good on his word and lives with Lisa and her son for a year.

The trouble is Dean is restless in his suburban life. He knows what goes bump in the night, and by ignoring it he’s suppressing a major part of himself. Maybe there’s no way to live a normal life and hunt. Dean ultimately tries and fails, leading to Lisa and her son’s memories of him being erased.

6 BEST: DEAN AND ANNA

Supernatural Dean and Anna

Dean and Sam met Anna when she started hearing angels. What they didn’t know and she didn’t remember was she was a fallen angel. She’d removed her grace and become human. Now that she was back on the angels’ radar, however, she was a target.

On the run with the Winchesters, she and Dean found they had a special connection. Their romance had a lot of potential but outside of one night in the back of Dean’s Impala, the relationship was never given the opportunity to develop.

5 WORST: SAM AND RUBY

Supernatural Sam and Ruby

Lots of fans loved Sam and Ruby. He may have been a hunter and she may have been a demon but they had the kind of chemistry that made fans root for them. Plus, Ruby was far more supportive of Sam as he started to explore and learn to control his demon powers than Dean was.

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For most of Season 4, her desire to help Sam seemed like it might even be genuine.  Of course, right at the end of the season it became clear that she’d been playing him the whole time. Fortunately, Sam didn’t give the demon too much time to revel in her victory before he ganked her.

4 BEST: CESAR AND JESSE

Supernatural Jesse and Cesar

Supernatural’s track record on LGBTQ representation hasn’t always been stellar. However, one of its bright spots was this married couple who helped the brothers on a case in Season 11. While their relationship took a backseat to hunting the monster of the week, it was clear that these two were happily married.

After successfully defeating the Bisaan that had killed Jesse’s brother Matty 27 years earlier, they gave Matty’s body a proper hunter’s burial. Then, the couple announced their plans to retire from hunting. It was a rare happy ending for one of the show's relationships.

3 WORST: KETCH AND MARY

Supernatural Ketch and Mary

Arthur Ketch was the ethically dubious British Man of Letters who came to the States to eradicate the supernatural. While the goal of the group was to recruit the Winchester brothers to their mission, Ketch was far more interested in Mary, who he discovered was a fantastic hunter in her own right. The recently resurrected Mary, who was feeling lost and confused, got on board with his mission, and even left her sons to hunt with Ketch.

In the process, the pair started a romance. Although it may have been driven by the adrenaline of the hunt, Ketch did have feelings for Mary. Unfortunately, he expressed those feelings by having her brainwashed so she’d do his bidding without objections.

2 BEST: SAM AND JESS

Jess was Sam’s college girlfriend. They met while Sam was at Stanford doing everything in his power to escape his family’s hunter lifestyle. Just as he was about to get into law school and propose to Jess however, Dean arrived to enlist Sam’s help in finding their father.

Sam returned to school, just in time to see Jess suffer the same fate as his mother, pushing him back into hunting and a quest to find Jess’ killer. Jess represents a time in Sam’s life when he had a shot at traditional happiness. Her death represented the tragic end of that possibility.

1 WORST: SAM AND BECKY

Perhaps the worst couple in the show’s history was Sam and Becky. Becky was first introduced in Season 5 as a terrible caricature of a fan. She was completely obsessed with the show’s Supernatural series of books and had an enormous crush on Sam, who wasn't interested. It was an insult to Supernatural fans everywhere.

Despite that, the writers decided to have her return in Season 7. This time she had a love potion that made Sam believe he returned her affections, leading to their hasty marriage. To say the story line was icky is an understatement. It was one of the show’s low points. Thankfully, we haven’t heard from Becky since.

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