Supernatural is complicated. Family, friends, monsters, hunting, life, and death — none of it is simple. The Winchester brothers are often faced with impossible odds, but despite all, they overcome it just in time to be hit with another obstacle. Yet they handle things in such a way that keeps us latched on, because we feel for them and their story so deeply that we just have to know how it works out. One of those things we kept a high interest in was the Winchester brothers' and friends' relationships. Some we loved, some not so much. Here are 5 relationships we supported — and 5 we totally rejected.
Rejected: Dean & Anna
Really, who bought into this relationship? Anna (Julie McNiven) starts out as a young woman requiring protection from angels and demons — Dean's specialty. Turns out, Anna's an angel herself. You'd think that would throw Dean off, considering he seems to have a self-imposed policy against dating anyone supernatural, but instead the two spend a night together. They shared something of a connection, but we knew it wouldn't last, and honestly, we weren't completely into their relationship. What really drew the line was when she went back in time to kill Dean's parents so Sam could never be born...yeah, definitely not girlfriend of the year.
Supported: Sam & Jessica
Literally from the very first episode, we could see how happy Sam and Jessica (Adrianne Palicki) were together. Though she only lived for one episode, we were rooting for her and Sam to have their normal life while Dean returned to hunting. Throughout much of the first season, we sympathized with Sam as he grieved for Jessica and blamed himself for not warning her sooner. Jessica may have been the best relationship Sam ever had, and it was over too soon. We still grieve with him.
Rejected: Sam & Amelia
Amelia (Liane Balaban) seems nice enough. A young woman looking for a new start following an unexpected tragedy in her life. She meets Sam shortly after he loses Dean to Purgatory. Perhaps we were wondering why Sam wasn't more occupied with finding and retrieving Dean than pursuing what we knew would be a doomed relationship with Amelia. The writers must have agreed, because Amelia's thought-to-be-dead husband comes back and Sam leaves, deciding to remove himself from the picture to give them another chance. We all know Sam ends up back with Dean, but he spends a few episodes in Season 8 contemplating what could have been with Amelia. We're sorry Sam went through another failed relationship, but Amelia just wasn't "the one" for him.
Supported: Sam & Sarah
Sarah (Taylor Cole) is the first love interest Sam has following Jessica's death. Sarah helps Sam and Dean destroy a cursed painting, daring to risk her own life in the process. She was brave, and certainly understanding of Sam's situation. It seemed she was just what Sam needed following his tragic loss, but alas, Sam wasn't quite ready for another relationship and as always, he had to leave town to continue hunting with Dean. We saw Sarah again in Season 8 briefly, learning she moved on and happily married someone else, but she is tragically killed by Crowley (Mark Sheppard) in a revenge plot against the boys. Poor Sam doesn't have much luck with the ladies, especially when it pertains to keeping them alive.
Rejected: Mary & Ketch
We weren't thrilled when Mary (Samantha Smith) went to join the British Men of Letters behind her sons' backs in the first place. Taking up a relationship with the then-unlikable Ketch (David Hadyn-Jones) wasn't one of her greatest hits, either. Her relationship with Ketch came across as something closer to betrayal. Ketch even encouraged her to forget about Sam and Dean. Mary kills him, but thanks to a spell of Rowena's (Ruth Connell), he is resurrected in time to redeem himself by helping the Winchesters in the apocalypse world. We may like Ketch a little more now, but that doesn't mean we'll ever support his past relationship with Mary.
Supported: Dean & Castiel
Okay, this is more of a shipped-by-the-fans relationship. It hasn't actually been carried out onscreen. Fans have been shipping them two for years now; they even have a coupledom name, "Destiel." According to fans, Destiel's is more of a between-the-lines kind of relationship. Whatever it may be, their relationship is wholeheartedly supported in the world of fanfiction. Meanwhile, onscreen, Dean and Castiel (Misha Collins) are merely a human and angel that were initially enemies but became best friends over the years.
Rejected: Dean & The Darkness
Dean struggled with his feelings for The Darkness, aka Amara (Emily Swallow), God's sister, following her appearance beginning in Season 11. She had a soft spot for him given that he released her (unintentionally). But we had a hard time buying the whole thing. Really, Amara was vengeful and spiteful. She committed plenty of terrible acts simply to get God's attention. What could Dean ever see in that? Plus, again, she's a supernatural being, and one of the most powerful at that. If anything, that would go against Dean's dating agenda. Although, she did give Dean his mother back before leaving with God, so she may not be all bad. But we still don't like her and Dean as a couple.
Supported: Rowena & Gabriel
In a memorable Season 13 episode, Rowena and Gabriel (Richard Speight, Jr.) share a moment of witty banter when they are left alone while helping Sam and Dean. Hilariously, Sam, Dean and Castiel later walk in on Rowena and Gabriel sharing a very heated moment in the library. Fans seemed to support this; we were surprised and amused by their sudden relationship. It makes sense if you truly consider it; they're both beings of the supernatural variety and they've both had their share of alternating between being good and bad. They have lots in common, and we think they'd make an adorable couple. However, Gabriel was killed in apocalypse world before anything could really happen between them. Sigh.
Rejected: Sam & Ruby
Ruby (Genevieve Padalecki) is a master liar and manipulator. She uses others to get what she wants without remorse. Her relationship with Sam was founded on lies. Truly evil lies, since we know her intention was to use Sam to free Lilith (which she did, but the boys killed her shortly afterwards). Ruby got Sam addicted to demon blood and turned him into something of a monster, and Sam went through Hell to detox from its effects. While Jessica is Sam's best relationship, Ruby is without a doubt Sam's worst. We weren't sorry when the Winchesters killed her.
Supported: Jo & Dean
Fans lobbied for them to happen from the get-go. The two have a flirty relationship that exuded utmost potential. Yet at least according to both Jo (Alona Tal) and Dean, it was never the right time for them to get together. That, or they simply just kept dodging the other's affections. The two had a lot in common between their hunter fathers and their interests in hunting; fans were dying to see how it would go. We were as heartbroken as Dean when he had to leave the wounded Jo in Season 5 to die in a fiery explosion with her mother to get rid of a pack of hellhounds.
We did get to see Jo one more time in a Season 7 episode when she appeared as a ghost, which offered a tender moment between her and Dean before she was nearly forced to kill him. Sometimes love just isn't meant to be, but that doesn't mean we're not still hoping for Jo to come back in the final season for one last moment with Dean.