Supernatural is currently on its 13th Season and chugging ahead with uncanny strength. The longer the show runs, more and more fans are drawn to the tale about two brothers who fight evil and save the world. Supernatural has a bit of everything for everybody and that’s part of its charm. It doesn’t matter what you’re looking for; Supernatural has it in spades. While the show revolves around Sam and Dean Winchester battling vampires, demons, gods, and sometimes each other, Supernatural’s central draw is the emotion laden within is linings and the characters themselves.

Relationships play a big part in the TV show. Without the bond shared by Sam and Dean Winchester, Supernatural would be substantially poorer. Over the course of the many seasons the show has run for, there have been many characters who have sided with or against the Winchesters. While many have died or gone their separate ways, these relationships were nearly as crucial, and sometimes more so, than that shared by the brothers. Unfortunately a few of these relationships were either not terribly received by audiences or were simply questionable in nature. Today at CBR we’re taking a look at 15 of the most controversial relationships in Supernatural.

15 SAM AND RUBY

Sam just can’t catch a break when it comes to love. In the case of the demon Ruby, things went from bad to worse the moment she entered the Winchesters' lives. At first, it was difficult to tell whether her intentions were benign or malicious. As her time with Sam grew, we realized she had nothing but evil cooking.

While Dean was in Hell, Sam was more lost than ever before. Ruby swooped right in, whispering sweet nothings in Sam’s ear and getting him addicted to drinking sickening amounts of demon blood. Eventually their relationship graduated, becoming sexual in nature until Sam was nearly fully reliant on Ruby. The whole time she was actually molding Sam into the perfect vessel for Lucifer, manipulating him every step of the way. Thankfully, Dean intervened before her machinations could be fully realized and killed her.

14 DEAN AND THE DARKNESS

After Dean Winchester tampered with the Mark of Cain, the Darkness was unleashed. The primordial dark energy was actually the sister of God; the Darkness took on the form of a woman and was named Amara. Because it was Dean who effectively set her free, Amara harbored a strong affection for the Hunter, boarding on lust. Even Dean felt overwhelmingly compelled and drawn to her, unable to resist the malevolent deity.

Though Dean was aware Amara planned to kill God and wipe out creation, he was emotionally torn between his responsibility to save the world and his desire to make out with the Darkness. It didn’t help matters that she made a vow that neither one would hurt the other. As Supernatural relationships go, it was a rather confusing one. It was also simply unusual to see Dean written into a romantic relationship with the deadliest being in the universe.

13 SAM AND LUCIFER

Lucifer plays a big part in the Supernatural mythos. There are entire seasons dedicated to the Devil’s threat. During it all, it was revealed that Sam was his chosen vessel and that they were meant to be together. Should Lucifer fully bond with Sam, it would allow the fallen angel to acquire the power he needed to take over the Earth. Their relationship was incredibly disturbing, with Lucifer getting a kick out of driving Sam closer and closer to the psychological edge.

With the aid of Ruby, who made Sam drink large amount of demon blood to prepare his body for Lucifer, the devil nearly succeeded in fully bonding with the Winchester. The entire time Lucifer plagues Sam acts out like a massive game of cat and mouse. Once Lucifer gets ahold of Sam’s body (for a short time), he killed fan-favorites like Castiel and nearly killed Dean.

12 CROWLEY AND THE WINCHESTERS

Why trust a demon that has sought to murder you multiple times? That’s the question Supernatural perpetually asks whenever the Winchesters partner with the evil demon Crowley. Though it’s an odd and counterintuitive relationship, it is one of the most entertaining unions in the series. What’s somewhat controversial about Sam and Dean hanging out with Crowley is not just that he’s a demon who’s killed tons of people and managed Hell. Rather, Crowley has been responsible for killing their friends and manipulating their family.

He’s even tried to murder the brothers on multiple occasions. Over the years, Crowley has gotten kinder. He’s teamed up with the Winchesters when the fate of the world was at stake, but it doesn’t necessarily make sense that they’d become legitimate friends, considering all the horrible things he’s done to them.

11 SAM AND MADISON

Even in the Supernatural’s early seasons, love had no place in the life of Sam and Dean. At one point in season two, Sam came across the woman Madison. Though they had a connection, any hope of a future was immediately dashed on account of her being a werewolf. Even though she’s already killed her boyfriend and one or two other people, Madison is especially apologetic about her deeds and wants to live a normal life. Shenanigans ensued and Sam and Dean killed the werewolf who transformed her and then believed they cured her.

From there, Sam and Madison slept together and there was the suggestion that maybe the two could make something work between them. Such happy tidings didn’t last. Madison reverted to her werewolf form again. When she returned to normal, she begged Sam to kill her. With no apparent alternative, he did just that.

10 DEAN AND BENNY

One of the more intriguing relationships in Supernatural’s lengthy tenure was the brotherhood formed between Dean Winchester and the vampire Benny. After Dean ended up in purgatory, he was constantly fighting for his life against increasingly overwhelming odds. It was in the null space between Heaven and Hell he met a kindred spirit in the form of Benny, a creature of the night.

Banished to Purgatory by his vampiric master, Benny saved Dean from another vampire and the two became fast friends and blood brothers. Their relationship was such that Benny meant more to Dean than Sam; the younger Winchester had given up looking for his big brother. When Benny and Dean make it back to Earth, Sam had nothing but mistrust for the vampire. Ironically, Benny ended up sacrificing himself for Sam, proving to both the younger Winchester and the audience that even vampires can be human.

9 SAM AND GADREEL

In trying to close the Gates of Hell, Sam endured a gauntlet of Trials. Though he completed them, the effort nearly killed him. Desperately, Dean prayed to any angel to help and is assisted by the angel Gadreel. The angel is also weak, after having just fallen from Heaven. Explaining that inhabiting Sam will heal them both, Dean reluctantly makes the deal. Gadreel says that Dean mustn’t let know Sam otherwise the angel would be expelled from Sam’s body, potentially killing them both.

Once the deed was done, Sam was back on his feet, but not everything is hunky dory. Even though Dean originally made the pact to save his brother, he’s constantly forced to lie to him. After a time, things become overly complicated and no one is left particularly amused. The emotional cost for Dean, and the audience, was high, especially since the possessed Sam kills Kevin.

8 THE WINCHESTERS AND ADAM

Sam and Dean constantly stress the importance of family and how it’s the single most essential thing for them. After their dad went missing and later died, the brothers took it upon themselves to provide one another with the familial affection they never adequately received growing up. Then in season five, it was revealed they had another brother: Adam. At the end of the season, Adam was thrown into the Cage along with Lucifer and then never gets seen again.

The revelation that John Winchester had in fact sired another son was pretty intense, but the show didn’t utilize the extra brother in a meaningful way. After Adam “died”, Sam and Dean went about their way and didn’t look back. For two brothers who break every cardinal rule of magic just to keep the other safe, you’d think they do the same for the third Winchester brother. They didn’t.

7 MARY AND KETCH

In the grand scheme of things, Mary Winchester was the driving force for the Winchesters becoming hunters. After she was murdered, her husband and the boys would effectively fight forevermore to avenge her. She’d later be resurrected nearly 20 years after her death. Along the way, she teamed up with the British Men of Letters, a brutal supernatural intelligentsia with sights on wiping out all paranormal creatures.

Mary struggled to connect with her sons, seeing as they were grown men, but she found a bizarre kinship with the Men of Letters, and in particular Arthur Ketch. The Men of Letter’s deadliest henchman, he and Mary became temporary partners both on and off the field of battle. Considering the Men of Letters had tortured Sam and nearly killed Dean, it was more than peculiar and a tad frustrating to have Mary team up with the dark group.

6 THE WINCHESTERS AND GRANDFATHER SAMUEL

Samuel Campbell was the father of Mary Winchester and the grandfather of Sam and Dean. In season six ix, after Dean is reunited with Sam who he thought to be dead, he sees his younger (soulless) brother is now working side-by-side with their crotchety grandfather. From the moment they started working together, Samuel cared little for his grandkids; he was more concerned with using them for his own ends.

It made for a complicated matter since Samuel both didn’t mind using overly harsh methods in dealing with the supernatural. Most importantly though, he was actually working for Crowley to try and discover the location of Purgatory. To that end, Samuel both manipulated his grandsons and refused to help them in their fight against Crowley. Turns out, Crowley promised Samuel he would resurrect his daughter, Mary. It doesn’t work out for anyone and Samuel was killed.

5 DEAN AND JO

An early fan-favorite Supernatural character was the young hunter Jo Arvelle. The daughter of one of John Winchester’s hunting friends, she and Dean quickly formed a bond. The two would often flirt, and despite Dean’s efforts, they would remain platonic friends. After a time, Dean and Jo started acting more like brother and sister and that was okay. On some level, many fans felt that Jo was far too young for Dean and that it would be creepy if they developed a sexual relationship.

At one point, a possessed Sam mocked Jo by saying Dean only saw her as a little sister. Later in season five, Jo gets torn apart by Hellhounds. As she’s dying, Dean kisses her on the forehead, and then on the mouth. The kiss didn’t appear romantic but more of a send off, but was the kiss for Dean or Jo?

4 CASTIEL AND DEAN

The moment Castiel landed in Supernatural, the character was a bona fide hit. Helping the Winchesters in their battle against the Devil and then eventually every other evil that crossed their paths, the angel quickly became a member of the Winchester family.

To be clear, there’s nothing negatively controversial about Castiel and Dean, but it’s more the relationship the fans desired to see between them that gets a mention here. Though Castiel would be friends with both brothers, he seemed (or at least viewers felt) that he favored Dean. From there, the fan art, fan fiction and shipping between the two characters, known as Destiel, started, and continues on to this day. Almost inexplicably, a large group of Supernatural fans just adore the idea that Castiel and Dean harbor a secret and unrequited love for one another.

3 DEAN AND LISA

The Winchesters are Hunters, partly because that’s the only thing they know. Rarely do they find chances at normalcy. However, such an opportunity presented itself to Dean in Lisa. The two had met eight years before season three, but nothing really came of it. They met again in seasons three and five, when Dean thought Sam was dead, he looks for Lisa and her son, Ben.

Dean retires from the hunter life and moves in with Lisa, acting as a surrogate father to Ben. It’s going pretty well until Crowley’s demons abduct them. Though Dean saves the pair, Lisa ends up in the hospital and her son is distraught. Realizing he’ll always have enemies, Dean has Castiel erase their memories. Lisa and Ben offered hope for Dean; it was cruel to rip them out of his life. It’s a relationship that’ll always be sadly remembered by the fans.

2 JOHN WINCHESTER AND HIS SONS

John Winchester didn’t always start off as a tough-as-nails militant father. Rather, it was his wife Mary who was the Hunter of the family. After she was brutally murdered by the Yellow-Eyed Demon, John went off the rails. He committed himself fully to hunting and killing the supernatural and enlisted his two young boys to help him.

John became unhealthily obsessed with killing the demon that murdered his wife, so much so that his relationship with Dean and Sam became not one of family. Instead, they were a means to an end, something to train in case he failed. He brought them along since they were his kids, but Sam and Dean never felt close to their father. They would end up feeling both manipulated and unloved by him as they got older. They didn’t have a healthy relationship by any stretch of the imagination.

1 SAM AND DEAN

Considering how Sam and Dean are Supernatural’s central protagonists, it’s easy to overlook just how dysfunctional and controversial a relationship they have. Trust is not an easy commodity; they are constantly at odds with the other and second-guess each other’s interests.

Additionally, Sam and Dean appear to be overly codependent. The Winchesters inexplicably can’t seem to operate unless they are together. They do everything together, go everywhere together, and neither Sam nor Dean are especially thrilled if someone gets between them. Though the brothers lazily dream about leaving the hunting life, the moment they get the opportunity, they seek the comfort in each other and the familiar, rather than try and stay in a functional relationship with anyone else. Their relationship is almost cyclical in nature; they punch each other, argue, express affection, and then the whole process repeats.