Eileen Leahy comes into the Supernatural series in Season 11 but she and Sam didn’t hit it off right away. Later, they developed a relationship that, like everything in this series, had many ups and downs. They shared their lives as hunters and they remained independent at the same time, even when it led to their downfall.

Sam Winchester is a secret hero to the world of hunters but Eileen didn’t know him when they first met. The stories of how he and Dean saved the world many times over didn’t do much to impress her. But Sam still granted her the respect he would any other hunter and even when his protective instincts kicked in, he tried to let her always be herself.

10 Perfect Couple: Eileen Recognized Sam As A Hunter

When Eileen was introduced in Season 11, she trapped Sam and mistakenly thought he was the banshee they were both hunting. When he told her he was a hunter like her, it didn’t take much for her to recognize him as such and let him go. Eileen had only a few seconds to decide if she would kill him or accept his claim and at that moment, she knew he was like her.

They hit it off quickly with witty banter and talk of their backgrounds in hunting, as well as their upbringings. In the end, Sam even revealed the location of their hidden bunker and told her to come by anytime she needed.

9 They Don’t Work: Eileen’s Dangerously Impulsive Nature

Even though Eileen did recognize Sam as a hunter after he made his claim, she still almost killed him when they first met. Had she done a little more research instead of jumping into action, she might have known that from the start. In Season 12, Eileen shot at Dagon with the Colt.

She knew that it could kill almost anything but didn’t know much about Dagon’s powers or who she was. Her impulse to shoot first got Renny (from the British Men of Letters) killed and marked her for death. She also kept the Colt after shooting Dagon.

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8 Perfect Couple: Sam And Eileen Are Both Men Of Letters Legacies

In her debut episode, Sam and Dean learn that Eileen’s grandfather was a Man of Letters, just like their grandfather was. This makes her a legacy and means that she shares an important history with Sam. Like many other Men of Letters, Eileen and Sam are both inquisitive researchers that always want to learn more.

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Eileen and Sam have a lot of fan-favorite moments in the Men of Letters bunker that Sam and Dean call home. They’re comfortable there and they both love books and spells as much as they love hunting.

7 They Don’t Work: Eileen Ran And It Got Her Killed

When Eileen shot Renny and accidentally killed him in Season 12, the British Men of Letters wanted her killed in retaliation. Sam talked Mick out of this course of action and invited Eileen to stay at the bunker with him and Dean, where it was safe.

He wanted her to stay with them so that he could protect her, but she ran back to Ireland. Once Mick was killed, Arthur Ketch sent a Hellhound after Eileen in Ireland and killed her. Her impulse to run instead of staying safe at the bunker with Sam led to her death.

6 Perfect Couple: As A Ghost, Eileen Saves Sam’s Life

In the episode “Golden Time” in Season 15, it is revealed that Eileen was dragged to Hell by the Hellhound that killed her.  Sam is after a witch and comes up against someone who he may not be able to beat by himself. As a ghost stuck in the veil due to Chuck/God’s rift earlier in the season, Eileen gets to Dean, tells him that Sam needs help, and effectively saves Sam’s life.

Sam and Dean learned that once a soul has been touched by Hell, it can’t go back.  Eileen knew that and saved Sam anyway, knowing there was nothing in it for her.

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5 They Don’t Work: Sam’s Fated Destiny

Throughout the series, Sam has ended up in several tricky situations that were not conducive to keeping a relationship. He almost died and Dean made a deal with a demon to save him. He jumped into the pit and went to hell to stop the apocalypse. He insisted on doing the trials to close the gates of hell and almost died again. And even in this last season, he shot at Chuck/God with The Equalizer knowing that it could lead to his own death.

Through all of these fated destinies, Sam doesn’t appear to have a long lifespan. Eileen doesn’t seem like the “normal life” type but in the end, falling in love means someone is bound to get seriously heartbroken.

4 Perfect Couple: Sam And Dean Both Learn Sign Language

Eileen shows, through her actions and character traits, that she doesn’t need anyone to help her get around, but Sam and Dean still do their best to accommodate her and show respect by learning sign language.

It wasn’t necessary for Sam to be able to speak Eileen’s language but it’s a sign of how well they work together that he and his brother were both willing to make sure it was easy to communicate with her. It shows that Sam wanted to keep Eileen in his life for a long time.

3 They Don’t Work: Eileen Doesn’t Trust Sam Completely

In order for a couple to be “perfect” together, there needs to be ultimate trust. In the Season 15 episode, “Our Father, Who Aren’t in Heaven,” Sam shows up on Eileen’s werewolf hunt. She is suspicious of his motives and asks him if he’s been following her.

Later on, in the episode “The Gamblers,” Sam says that he’s been in touch with Eileen and she believes their plan to defeat Chuck/God is “too good to be true.” In the episode “Last Holiday,” Sam talks about Eileen being in town and they go on a date but Eileen doesn’t join the fight with them.

2 Perfect Couple: They Can Be Independent Together

At first, Eileen’s independence isn’t an item in the pros column for Sam and Eileen’s relationship. But later on, after Sam resurrects her from the dead, he becomes more overprotective than ever. Eileen’s character known to that point would have her running away instead of letting herself get attached.

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Instead, she talked to Sam when a friend wanted her to join a hunt and she thought she might be in over her head. Previously, she acted on impulse, sacrificing her better judgment in favor of independence. Presently, she includes Sam and works with his overprotective nature.

1 They Don’t Work: Sam’s Ultimate Sacrifice To Save Eileen

Sam has his own fated demise written in Billie’s books over and over but one outcome he never imagined was that Billie would take Eileen away from him if their plan succeeded. In the Season 15 episode, “Unity,” Sam is willing to sacrifice the whole universe to make sure Billie’s plan doesn’t come to fruition because that would mean losing Eileen.

In retaliation, Chuck/God “detonates” Jack. Sam’s ultimate sacrifice could mean the end of the world, all to keep Eileen from going back to the afterlife.

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