Either through temporary goodbyes or, more often than not, through deaths, Supernatural pulled at the heartstrings by separating characters.
For fifteen years, fans grew more and more attached to the characters of Supernatural and the relationships between them. Time and time again, though, the show ripped at the heartstrings of fans by separating characters, either through temporary goodbyes or, more often than not, through deaths that affected audiences and characters alike.
Dean Sends Benny Back To Purgatory
Despite the duo arguably not spending enough screentime together, fans grew pretty attached to the Benny/Dean dynamic of season 8. They were sad both when Dean decided to cut contact with Benny and when he sent him back to Purgatory.
Dean did not kill Benny as an evil act, or because Benny acted monstrously, instead it was so Benny could rescue Sam from Purgatory, indicative of how truly good Benny was. The fact Benny never returned from the place where monsters go when they die makes it all the more painful when the two hug goodbye.
Rowena Sacrifices Herself
In terms of anti-heroes and redemption, Rowena MacLeod had one of the best arcs in Supernatural, and while she did return as the Queen of Hell not long after, the final death of the fiery Scottish witch hit hard.
Not only did it affect her fans, but the Winchesters too, particularly Sam. Bonded through their fear of Lucifer and Sam’s natural inclination for studying and understanding magic on a basic level, the two formed a great relationship. Rowena became yet another loved one of the Winchesters that they lost.
Dean Has Lisa & Ben’s Memory’s Erased
Fans are still divided on the relationship between Dean and Lisa, a romance that was doomed from day one, really. Some believe the two were a great couple and Dean deserved the happiness and comfort of their life, while others believe they simply were not all that.
Either way, it is genuinely heartbreaking when Dean decides to have Cas erase him from their memories. When he tells Sam he will punch him should he mention them again, fans felt nothing but sympathy for him – and for Sam, who knew how Dean felt. The fact that Dean never found love again after this, except for Cas, or anything close to an apple pie life makes the separation all the sadder.
Mary Left The Bunker
Supernatural fans who like Mary Winchester are few and far between. One of the moments that make fans hate her the most is when, after not very long back from the dead, she decides she needs time away from Sam and Dean.
Now, from a fan perspective, this is pretty infuriating. However, in terms of sympathizing with Sam and Dean, who takes it especially hard, this is a truly heartbreaking moment. Dean is so hurt. He just got his mom back, something he had dreamed of for decades. Now, she needs away from him, saying she does not really know him like how he knows her. It is difficult not to feel great sadness for the boys in this scene.
John Dies (& When He Went Back To His Own Time)
John Winchester’s death in the premiere of season 2 took so many fans by surprise, and seeing how Sam and Dean had to deal with that was definitely tough. After his cameo in “All Hell Breaks Loose,” fans never expected to see him again.
Twelve years later, though, Supernatural’s 300th episode came around, and Jeffrey Dean Morgan reprised his role as the Winchester patriarch. Through this episode, the family got so much closure. However, with that came another heartbreaking separation as the boys had to give up their father.