Across its 15 seasons,Supernaturalgave Dean Winchester many love interests. Surprisingly, despite his reputation as a ladies' man, Dean had about eight love interests from the opening episode until the end ofSupernaturalseason 15. Dean was more jaded than Sam, at least to begin with, and guarded his heart fiercely. This meant that he chose his most meaningful relationships very carefully. However, that didn’t stop him from engaging in flings and one-night stands off-screen, earning himself his reputation. Whether Dean or other characters,Supernaturalhad some great romancesthrough the years.
Eric Kripke’s critically acclaimed TV show puthunter Sam Winchesterand his brother, Dean, into dangerous situations with various monsters and their family business didn’t help Sam and Dean develop long-term relationships. This was a theme throughout the show, which dived into the interpersonal difficulties that came with traveling across the U.S. to save people from demons, vampires, werewolves, and more. But through it all, Dean’s most important long-term relationship was with his beloved little brother, Sam. Sam was Dean’s constant through the women that came and went in his life – though there were definitely a few important women in Dean’s history.
8Layla Rourke
Season 1
Layla Rourke appeared inSupernaturalseason 1 as a troubled woman that Dean wanted to save.Dean’s inability to help Layla was reflective of his main problem in life- he couldn’t save everyone. Dean had a definite hero complex buried underneath his rough cynicism and bravado.Supernaturalused Layla to reveal this facet of Dean’s personality while maintaining one of the most gripping storylines of season 1.
Supernaturalseason 1, episode 12, “Faith,” aired on June 23, 2025.
Layla and her mother were Christian visitors of Roy le Grange, aSupernaturalseason 1 faith healer. Suffering from a brain tumor, Layla was hoping that Roy could cure her.Supernatural’sWinchester brotherssoon revealed Roy as an impostor, highlighting Kripke’s talent for critiquing and satirizing real-world issues and ideas with his fantasy series.Dean severed Roy’s dangerous relationship with the reaper in “Faith,” leaving Layla incurable, having only just formed a bond with Dean.
7Cassie Robinson
Cassie was a truly excellent match for Dean Winchester. InSupernaturalseason 1, Cassie presented a far better match than Layla ever had. Layla’s calm strength was good for Dean, and could have helped him settle down, butCassie was the fiery partner that could have changed Dean’s life. Unfortunately, Dean’s hunter lifestyle made his relationship with Cassie too difficult to continue. This relationship had legs inSupernatural, so it was a shame that it wasn’t explored further.
Supernatural Set Up A Totally Different Sam & Dean Winchester, But Needs Season 16 To Pay It Off
Supernatural subtly created a totally new Sam and Dean Winchester, and season 16, should it ever happen, could pay off this unresolved tease.
Supernaturalseason 1showed Dean reigniting his old flame, Cassie, in episode 13. “Route 666” offered a fascinating glimpse into Dean’s life before his father, John Winchester, went missing.Dean was a tough nut to crack for the show’s first few episodes, and Cassie revealed his softer side, showing that he was capable of commitment, like Sam. It was a shame that Cassie and Dean didn’t work out, but fans were treated to a hilarious revisit of her character in season 4, in “The Monster at the End of This Book.”
6Carmen Porter
Season 2
Carmen Porter’s appearance inSupernaturalseason 2 provided Dean with another glimpse of romance, but it wasn’t long-lived. Unlike Layla and Cassie,Carmen wasn’t even real. Unfortunately for Dean, she was just a figment of his imagination. Dean was hunting a djinn in “What Is and What Should Never Be,” which resulted in him entering a temporary djinn-induced trance for a brief spell. This spell revealed what life could be like for Dean if he weren’t a hunter, and Carmen was the ideal girlfriend he envisioned for himself in this scenario.
This is one of the iconicSupernaturalepisodes that referencedBuffy the Vampire Slayer, one of Eric Kripke’s key influences. Honoring the famousBuffyepisode “Normal Again”, in which Buffy enters an alternate reality where she was never the Slayer,“What is and What Should Never Be” presented Carmen as a temptation, forcing Dean to weigh his priorities. But not even Carmen could dissuade Dean from hunting. As such, Carmen was a key plot device and a key love interest for Dean, proving that the family business would always come first.
5Jo Harvelle
Seasons 2, 5, & 7
One of the longest-running recurring characters onSupernatural,Jo Harvelle was a fun ride for viewers and Dean alike. Jo and her mother were long-suffering hunters, recuperating after the loss of Bill Harvelle - Jo’s father and the husband of Ellen Harvelle. Jo always seemed a little young for Dean, a fact which he may have agreed with - at first. But over time, Jo and Dean proved their suitability. It was refreshing to watch a woman chase Dean for once, instead of watching Dean flirt outrageously.
Jo proved that hunting made relationships hard, whether or not both participants were in the profession.
Jo allowedSupernaturala unique explorationof Dean in a relationship with another hunter. Cassie proved what a relationship with a non-hunter was like for Dean, so it was critical that the show explored the alternative. If it hadn’t, viewers would forever be wondering which female hunter could rescue Dean from loneliness. However, Jo’s death from a hellhound attack proved that hunting made relationships hard, whether or not both participants were in the profession. The end of Dean’s relationship with Jo was unbearable to watch, making for some of the best television of 2010.
4Lisa Braeden
Seasons 3, 5, & 6
AlthoughSam Winchester had more love interests than Dean, surprisingly,Dean exhibited perhaps the most serious relationship of the whole show with Lisa. Dean and Lisa had hooked up years ago and, nine years later, he sought her out again when he was just passing through, but it developed into something serious. Viewers were shown a fair bit of Dean’s life with Lisa and her son, Ben. ThroughoutSupernatural, Lisa showed Dean more empathy and unconditional love than perhaps anyone outside his family.
It is a popular head canon in theSupernaturalfandom that feelings existed between Dean and Castiel, but this pairing never became explicit.
The ending of Dean’s relationship with Lisa and Ben was one of the most heartbreaking things aboutSupernatural. After being targeted by the demon Crowley,Dean deemed it to be safer for Lisa and Ben to be removed from his life completely. Therefore, he asked the angel Castiel to remove their memories of him. In this sense, Dean’s Lisa romance wasSupernaturalat its best - a tragic but inspiring story about the sacrifice of heroes. Dean’s sacrifice would make itself apparent again and again, heartrendingly.
3Anna Milton
Seasons 4 & 5
Anna Milton was an intriguing presence inSupernaturalseasons 4 and 5, offering Dean a new type of love affair. A fallen angel, Anna was a morally gray character at a time whenSupernaturalwas rapidly becoming far more complicated.Anna suitedSupernatural’snew complexity, offering Dean some difficult choices. Nonetheless, Dean’s fascination with Anna led to a brief but passionate relationship. Anna’s beauty wasn’t enough to keep her tied to Dean, and she was eventually betrayed by Castiel.
Sam Winchester’s 10 Love Interests In Supernatural Explained
Sam Winchester has had many love interests throughout Supernatural’s 15 seasons, from Jessica Moore in the pilot episode, to Velma from Scooby-Doo.
Castiel’s traitorous deal with Heaven led to Anna’s capture by angels and removal. This would later become an even bigger issue than it was in season 4. Officially gone were the days of a simple, serialized crime procedural with a paranormal spin. AlthoughSupernatural’sdeepening concern with Heaven and Hell wasn’t popular with everyone, creating a degree of convolution, it renderedSupernaturala consummate long-term fantasy story with its own lore.Dean’s arc with Anna was key to this new level of lore, coming full circle in season 5.
2Robin
Season 9
Supernaturalseason 9 gave fans a snapshot of Dean’s life as a teen, showing Robin as the subject of his first kiss. Dean’s interplay with Robin was short but sweet, proving that Dean wanted to have a normal life at one point. Unfortunately, it seemed thatRobin was the first of Dean’s love interests to fall victim to his hunting lifestyle. Dean’s father moved the family away, leaving Dean to break up with Robin. This key exposition showed viewers the adorable and innocent young Dean Winchester that once existed, making his grizzled present existence more sympathetic.
The waitress, working at Cus’s Place, was a strangely appropriate foreshadowing of Dean’s life on the road.
“Bad Boys” was theSupernaturalseason 9 episode to show Dean’s clumsy first attempts at romance with Robin. The waitress, working at Cus’s Place, was a strangely appropriate foreshadowing of Dean’s life on the road - Dean lived out of a suitcase, eating at a different diner every other day. In general,Supernaturalwas always adept at showing the loneliness of life on the road. The show was not just a paranormal drama, but a road story, creating a metaphor for those who sacrifice stability for a disruptive but important job.
1Amara Schneider
Seasons 11 & 15
Amara Schneider may be the strangest of Dean Winchester’s love interests, coming into play fascinatingly in season 11. Amara was always a wild card, born to beleaguered human couple in a hospital but secretly becoming a vessel for the Darkness, the primordial entity and twin sister to God. These fascinating scenes referenced zombie apocalypse movies likeDawn of the Deadand28 Days Later, proving Kripke’s wide range of influences and Amara’s destiny. Linked to Dean from the start, Amara, as a baby, was entrusted to the Winchesters and Jenna.
However, Amara ended up being put through the ringer, growing up at a preternatural rate in order to provide the Darkness with a suitable host. This resulted in Dean’s last significant love interest - the adult Amara and Dean were strangely attracted to each other.The will-they/won’t-they couple danced around their mutual magnetism, toying with a common theme inSupernatural- forbidden love. In the end, not even the hugely powerful Amara could hold onto Dean, proving that his true love was his family.
Supernatural
Cast
Supernatural is a television series that follows brothers Sam and Dean Winchester, who were raised by their father to hunt and combat supernatural entities after losing their mother to a demonic force. Traversing the American landscape in their ‘67 Chevy Impala, they face numerous paranormal threats.
