Supernatural has mainly focused on family love and friendship throughout its seasons. We have the core family love between Sam and Dean, two brothers willing to do anything to protect the other. In addition, family and friendship are very important to the brothers as we see them run to help others with little regard for their own safety. With all of this, there appears to be little room for romance. However, we have many romantic moments, although they may be atypical.
In the earlier seasons, we may have seen more moments, but they're there in later seasons as well. For the Winchesters, a romantic gesture can be big because it brings a sense of ordinary to their extraordinary lives and other gestures are as epic as saving the world for the umpteenth time.
10 Gabriel Protects Kali From His Brother
Gabriel comes to the Pagan deities gathering where the brothers and other humans are stuck. When the brothers discover that Loki (the trickster god) is really Gabriel, they encourage him to stand up to his big brother, Lucifer. Gabriel wants no part of this. However, when he realizes that it's not just the Winchester brothers who are threatened by Lucifer, but also his former flame, Kali, he steps up.
Initially, he tries to get Kali to safety, but she refuses, insisting on fighting. So Gabriel finds a way to get her to safety, and he finally stands up to his brother. He puts himself in harm's way to help save her.
9 Young Amara Saves Dean From Crowley
Before Crowley was the Winchester's bf, he was a formidable foe. When Dean is in Crowley's lair, and Crowley wants to do him harm, Amara protects him. Since Dean was the one to free Amara, she feels bonded to him. All throughout her growth, she is interested in Dean, drawn to him. She doesn't want to hurt him, and he can't hurt her, even though she's the villain of this season.
Luckily, Amara grows up fast, otherwise, this bond feels a little uncomfortable. The next time they see each other, they're adults, and Amara kisses Dean, rather than eating his soul, which is a romantic gesture on its own.
8 Bobby's Wife Pretends She Doesn't Remember Her Death
Bobby's wife, Karen, is resurrected in Season 5. She is the reason why Bobby became a hunter as he had to kill her when she was possessed. Bobby loves having Karen back. He tells the boys that she doesn't remember that he killed her.
Later, we find out that Karen remembers everything, but she wanted to spare Bobby's feelings, and so she acts like she doesn't. However, since she knows what it's like to feel possessed, she notices when she feels herself start to change into a zombie. Able to alert Bobby and forgive him at the same time, she tells him to kill her.
7 Jess Celebrates Sam's Achievements
This may seem small, but in the grand scheme of things, this is a big romantic gesture for Sam. Jess may not know it, but Sam hasn't had a normal life. He hasn't been able to be happy about school since his family treats his decision to attend as a betrayal. After all, he chose to leave the family mission in order to attend college and become a lawyer.
When he scores high on his LSAT, Jess is proud of him. She toasts his victory in front of friends and celebrates him. Since Sam feels like his family doesn't value him and his achievements, this means a lot.
6 Meg Stays With Castiel to Protect Him
It was an unlikely pairing, but romance bloomed between Meg (a demon) and Castiel. Even though Meg had been an agent of Lucifer and a villain, she changed and became an ally to the Winchesters. She saw Castiel as her special person, something that she confessed to Dean. When Castiel is in a hospital, she becomes a nurse in order to watch over him. When he doesn't know he is Castiel, she is there to make sure that no harm comes to him.
It's the first time we have really seen Castiel romantic with anyone, and the pizza man taught him right as his learned-kiss seemed to awaken something in Meg. Could it be compassion? Love? Whatever it is, it causes Meg to be the romantic and protect him when he's defenseless.
5 Jo Sacrifices Herself For Dean
This was a love story we never really got to see develop, but if we had--it would have been an epic love. When Dean is pulled down by a hell-hound, Jo strays from the others in order to save him. She knows how bad hell-hounds are and how afraid Dean is of them. Unfortunately, this gesture leads to Jo getting attacked.
Later, we see Dean kiss Jo good-bye. Luckily, Jo does come back as a spirit in a later season, albeit briefly. Even in that moment, she shows love to Dean, telling him that she doesn't blame him for her death, even though he still does. It's clear that there was love between these two.
4 Lisa Takes Dean In and Makes Him Part of Her Family
After Sam goes to hell with Lucifer trapped inside him, Dean had promised to live a normal life. He shows up at Lisa's door, broken. She knows of his hunter past, but she doesn't ask questions. She takes him in, and she helps heal him. While she's very protective of her son, she allows Dean to be a part of their family.
She cares for him so much that she's willing to move her family when he says that they need to move for protection. When she notices that he misses the hunter lifestyle, she tells him to go for it, and that they will try to make it work long-distance. We'd love to see Lisa again in Season 15, perhaps with her memories of Dean back.
3 Eileen Gives Sam a New Sense of Normal and Hope
After Sam resurrects Eileen in Season 15, a romance blooms between the two. While making breakfast with your romantic interest may not seem a big romantic gesture, it is for Sam. He has always wanted a more ordinary life, so small and simple gestures mean the world to him. Earlier, we saw how much it meant to Sam that Jess celebrated him. So, it means a lot to Sam to have someone to make breakfast with, to joke with, and to brainstorm with. Eileen brings new energy to Sam, and she brings hope.
Since the Winchester brothers friend themselves in such a hopeless situation in Season 15, Eileen's humor, joy of life, hope, and positivity mean a lot to Sam. Of course, Chuck/God clouds this later on in the season, but for a beat, it was the sunshine that Sam needed.
2 Dean Drops Everything to Help Cassie
Dean's first love interest that we meet is Cassie. In Season 1, he receives a call from her, and he drops everything to go to help her. He reroutes their travels. It surprises Sam because he never knew that Dean had a love interest (beyond a one-night stand), and that Dean actually told Cassie the family secret.
While their romance was short-lived, it was intense and passionate. Dean is someone who stays on the family path and follows his father's orders, especially in the earlier seasons. He strayed from that path with Cassie, which shows how much she meant to him.
1 John Dedicates His Life to Mary's Memory
It's hard to remember that John wasn't always a hunter. However, the tragic death of his love, Mary, makes him one. His whole life is about avenging her death (and protecting people along the way). While John may not always have been the best father to Sam and Dean, his love and loyalty ran deep.
It also shows how important and strong this love was in that John never really lets go of Mary. She was his special person, which makes the one scene where we get a reunion all the sweeter.
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