Supernatural: 10 Relationships That Fans Knew Were Doomed From The Start

As with most things in Supernatural, nothing is easy when it comes to love in the show. Here are relationships that were always doomed to failure.

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A huge part of what makes Supernatural such a beloved show with a passionate fandom is the character dynamics. The theme of family, both blood and found family, is a significant aspect of the show’s fifteen-year run. Of course, friendship and family are not the only relationships within the show, romance has a place.

As with most things in Supernatural, nothing is easy when it comes to love in the show. Given the professions and priorities of the main characters, romances rarely go well, and while there are some with glimmers of hope, some are immediately sniffed out by fans as being ones that will end badly, quickly, or both.

10 Castiel (Emmanuel) & Daphne Allen

Daphne Allen is not the first love interest that will pop into fan’s minds, but she certainly is one of the strangest cases given that she was married to Castiel, was not up to any evil plot, and fans do not really know her fate.

Daphne and Castiel (who at this point was thought to be Emmanuel) got married after Daphne found Castiel wandering along a river naked akin to Greek mythology, although it is unknown if the marriage was ever legally binding or legally terminated. From the moment the famous Emmanuel walked through the door and revealed himself as Cas, fans knew this marriage would be a one-episode affair.

9 Lucifer & Kelly Kline

When he was initially introduced in the Kripke-era of Supernatural, it was pretty impossible to predict the longevity of Lucifer’s impact on the show and just how often he would be around in various stories.

Nobody could have really imagined him possessing the President of the United States and having a romance with his secretary either. As soon as fans see that Kelly Kline and the President have a secret relationship, they knew it would not end well for her. Of course, this short-lived romance led to the beloved Jack, but it also led to Kelly’s death, something that was pretty much guaranteed with Lucifer’s involvement.

8 Sam Winchester & Madison

In a post-Jess life for Sam, one of the first women to pop up and show and have a romantic connection with the younger Winchester brother was Madison, a lovely woman who ended up being a Werewolf.

Even before fans knew Madison was a Werewolf, their romance was doomed. Coming only a season after Jess’s death and slap bang in the middle of Sam getting used to the hunter life without his father, a romance was never on the cards. When Madison was revealed as a Werewolf, fans suspected there was one heartbreaking way it was going to end.

7 Gabriel & Rowena MacLeod

When two of Supernatural’s most popular recurring characters decided they were going to hook up after a bit of a romantic spark between them, it was a hilarious and joyous occasion. Unfortunately, fans all knew how it would end for Rowena and Gabriel.

Romances like this do not last in the show. It was comedic, fun, and light-hearted but short-lived. While it makes a lot of sense for the two to be attracted to each other, it was always going to be a fling. Gabriel’s final heartbreaking death came not too long after, ending things for the pair.

6 Mary Winchester & Arthur Ketch

From two fan favorites to two of the fandom’s biggest annoyances of the show’s final half-decade, Mary Winchester and Arthur Ketch’s casual romance was definitely a strange inclusion to the show that.

Just like everything that involved Mary Winchester post-resurrection, the romance felt quite forced. Fans knew that Sam and Dean would find out, and that Ketch would do something despicable (this being before his return as a protagonist), and everyone knew it would end badly for these two because of those factors.

5 Sam Winchester & Amelia Richardson

If there is one sure-fire way to get Sam and Dean to abandon something, give up on something, or end something, it is by giving them a choice between the said thing and his brother. For the relationship of Sam and Amelia, this is pretty much what happened.

With Dean back from Purgatory, Sam reunites with his brother, leaving Amelia to be with her husband, who was previously presumed dead. As soon as fans found out about Amelia and the flashbacks started, fans knew it was building towards a sad end for the pair, which came in the form of an encounter that saw Sam choose a life with Dean rather than the apple-pie life the brothers so often reference.

4 Dean Winchester & Anna Milton

A relationship that came far earlier in the show and was far less serious was that between Dean and Anna Milton, who have one of the show’s steamiest scenes in the Impala serenaded by “Ready For Love.” That, unfortunately, did not change the fate of the pair.

While they were not in an actual relationship and there was just a short-lived romantic spark, there was something more going on with Anna than what was being led on (which turned out to be that she was a fallen angel), and with this coming so early in the show fans knew it would not end pretty. Anna ends up becoming a recurring character who is an enemy of the angels, eventually meeting her end when she goes back in time to try and kill John to prevent Sam’s birth.

3 Sam Winchester & Jessica Moore

The first relationship in Supernatural that was not John and Mary was between Sam and Jess, and as soon as Sam says he is going back for the law interview, and this hunt with Dean is a one-time thing, fans knew something bad was going to happen to poor Jess.

Had Azazel not killed Jess, we would not have gotten Supernatural, there would have been that first hunt, and that was it for the brothers. Unfortunately, Jess had to die, or at least be gone, which happened pretty brutally, making us sympathize with Sam a lot while also making fans excited for what was ahead after that first episode.

2 Dean Winchester & Lisa Braeden

To say fans knew right from the get-go that Lisa and Dean would end in disaster is a bit unfair. When we first meet Lisa, she and Dean are not even together; there is just clear chemistry there. Even when Dean turns up to her door in “Swan Song,” it was not inevitably going to go bad.

However, mere seconds later, when the camera pans to reveal Sam there, alive, out of hell, that is the moment fans knew for sure that Lisa and Dean were doomed. Season six proved that, with Lisa and Dean ending despite their best efforts to make their life together work. This was the last time fans saw Dean have a life away from hunting, and after his relationship with Lisa, Dean was never quite the same; he reverted back to his old opinions of himself being destined to die on a random hunt undeserving of happiness and peace, seemingly undoing that aspect of his character development.

1 Sam Winchester & Ruby

Funnily enough, the only romance on this list that was initially supposed to succeed was the one everyone could see ending badly immediately between Sam and Ruby.

Sam and Ruby were initially supposed to end up together, that was until the real-life romance of Jared Padalecki and Genevieve Cortese changed those plans. Despite this initial idea, Cortese played Ruby in a way that made clear she was up to something more than just helping Sam, taking advantage of the love Sam clearly had for her. While at first, the relationship between the two may not have been so obviously destined to end in bloodshed, it quickly became clear to most that it was headed somewhere bad.

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