Throughout its 15 seasons, Supernatural gave Dean Winchester many love interests. Surprisingly, despite his reputation as a womanizer, Dean had about eight love interests from the opening episode to the end of Supernatural season 15. Dean was more tired than Sam, at least at first, and guarded his heart fiercely. This meant he chose his most meaningful relationships very carefully. However, this didn’t stop him from engaging in flings and one-night stands off-screen, earning a reputation. Whether it’s Dean or other characters, Supernatural has had some great romances over the years.
Eric Kripke’s critically acclaimed TV show put hunter Sam Winchester and his brother, Dean, in dangerous situations with various monsters and their family business didn’t help Sam and Dean develop long-term relationships. That was the theme of the entire show, which delved into the interpersonal difficulties that came with traveling across the United States to save people from demons, vampires, werewolves, and more. But through it all, Dean’s most important long-term relationship was with his beloved younger brother, Sam. Sam was Dean’s constant through the women who came and went in his life – although there were definitely some important women in Dean’s story.
8
Layla Rourke
Season 1
Layla Rourke appeared in Supernatural Season 1 as a troubled woman Dean wanted to save. Dean’s inability to help Layla reflected his main problem in life – he couldn’t save everyone. Dean had a definite hero complex buried beneath his cynicism and bravado. Supernatural used Layla to reveal this facet of Dean’s personality, maintaining one of the most emotional stories of the first season.
Layla and her mother were Christian visitors to Roy le Grange, a Supernatural healer from the first season. Suffering from a brain tumor, Layla hoped Roy could cure her. Supernatural The Winchester brothers soon revealed Roy as an imposter, highlighting Kripke’s talent for criticizing and satirizing real-world issues and ideas with his fantasy series. Dean broke off Roy’s dangerous relationship with the grim reaper in “Faith,” leaving Layla incurablehaving just formed a bond with Dean.
7
Cassie Robinson
Season 1
Cassie was a truly excellent match for Dean Winchester. In Supernatural In season one, Cassie put on a much better match than Layla ever had. Layla’s calm strength was good for Dean and could have helped him calm down, but Cassie was the fiery partner who could have changed Dean’s life. Unfortunately, Dean’s hunting lifestyle made his relationship with Cassie very difficult to continue. This relationship had legs Supernaturalso it was a shame it wasn’t explored more.
Supernatural The first season showed Dean rekindling his old flame, Cassie, in episode 13. “Route 666” offered a fascinating glimpse into Dean’s life before his father, John Winchester, disappeared. Dean was a tough nut to crack in the show’s early episodes, and Cassie revealed her softer sideshowing that he was capable of commitment, just 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.”
6
Carmen Porter
Season 2
Carmen Porter’s appearance in Supernatural season two provided Dean with another glimpse of romance, but it didn’t last long. 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 going into a temporary djinn-induced trance for a brief period. This spell revealed what Dean’s life would be like if he weren’t a hunter, and Carmen was the ideal girlfriend he imagined for himself in this scenario.
This is one of the iconic Supernatural episodes that referenced Buffy the Vampire Slayerone of Eric Kripke’s main influences. Tribute to the famous Buffy episode “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 temptationforcing Dean to weigh his priorities. But not even Carmen could dissuade Dean from hunting. As such, Carmen was a key plot element and an important love interest for Dean, proving that family business would always come first.
5
Jo Harvelle
Seasons 2, 5 and 7
One of the longest-running recurring characters in Supernatural, Jo Harvelle was a fun ride for viewers and Dean alike. Jo and her mother were long-suffering hunters, recovering after the loss of Bill Harvelle – Jo’s father and Ellen Harvelle’s husband. Jo always seemed a little young to Dean, a fact he may have agreed with – at first. But over time, Jo and Dean proved their suitability. It was refreshing to see a woman pursue Dean for the first time, instead of watching Dean flirt outrageously.
Jo proved that hunting made relationships difficult, regardless of whether or not both participants were in the profession.
Jo allowed Supernatural a unique exploration of 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 happened, viewers would always be wondering which huntress could rescue Dean from loneliness. However, Jo’s death from a hellhound attack proved that hunting made relationships difficult, regardless of whether or not both participants pursued the profession. The end of Dean’s relationship with Jo was excruciating to watch, making it some of the best television of 2010.
4
Lisa Braeden
Seasons 3, 5 and 6
Although Sam Winchester had more love interests than Dean, surprisingly, Dean displayed perhaps the most serious relationship on the entire show with Lisa. Dean and Lisa had gotten together years ago, and nine years later he reached out to her again when he was passing through, but it turned into something serious. Viewers saw a glimpse into Dean’s life with Lisa and their son, Ben. All over SupernaturalLisa showed Dean more empathy and unconditional love than perhaps anyone outside of his family.
The end of Dean’s relationship with Lisa and Ben was one of the most heartbreaking things about Supernatural. After being targeted by the demon Crowley, Dean considered it safer for Lisa and Ben to be removed from his life completely.. Therefore, he asked the angel Castiel to remove his memories. In that sense, Dean’s romance with Lisa was Supernatural at best – a tragic but inspiring story about the sacrifice of heroes. Dean’s sacrifice would become apparent again and again, in heartbreaking ways.
3
Ana Milton
Seasons 4 and 5
Anna Milton was an intriguing presence in Supernatural seasons 4 and 5, offering Dean a new kind of love affair. A fallen angel, Anna was a morally gray character at a time when Supernatural it was quickly becoming much more complicated. Proper Anna Supernatural new complexityoffering Dean some tough choices. However, 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 ended up being betrayed by Castiel.
Castiel’s treacherous deal with Heaven led to Anna’s capture by the angels and removal. This would later become an even bigger problem than in the fourth season. Officially, gone are the days of a simple, serialized crime procedural with a paranormal twist. Although Supernatural the deepening of concern with Heaven and Hell was not popular among everyone, creating a certain degree of convolution, making Supernatural a long-running consummate fantasy story with its own lore. Dean’s arc with Anna was key to this new level of lorecoming full circle in season 5.
2
robin
Season 9
Supernatural season 9 gave fans a snapshot into Dean’s life as a teenager, showing Robin as the subject of his first kiss. Dean’s interaction with Robin was short but sweet, proving that Dean wanted to have a normal life at one point. Unfortunately, it seemed that Robin was Dean’s first love interest to fall victim to his hunting lifestyle. Dean’s father moved the family away, letting Dean break up with Robin. This key exposition showed viewers what a lovable, innocent young Dean Winchester once was, making his grizzled existence more sympathetic.
The waitress, working at Cus’s Place, was an oddly fitting foreshadowing of Dean’s life on the road.
“Bad Boys” was the Supernatural season 9 episode to show Dean’s awkward first attempts at romance with Robin. The waitress, working at Cus’s Place, was an oddly fitting foreshadowing of Dean’s life on the road – Dean lived out of a suitcase, eating at a different restaurant every other day. In general, Supernatural has always been a fan of 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 disturbing but important work.
1
Amara Schneider
Seasons 11 and 15
Amara Schneider might be the weirdest of Dean Winchester’s love interestscoming into play in fascinating ways in season 11. Amara has always been a wild card, born to a beleaguered human couple in a hospital but secretly becoming a vessel for Darkness, the primordial entity and twin sister of God. These fascinating scenes referenced zombie apocalypse films like Dawn of the Dead and 28 days laterproving Kripke’s wide range of influences and Amara’s destiny. Bound to Dean from the beginning, Amara, as a baby, was entrusted to the Winchesters and Jenna.
However, Amara was ultimately put at risk, growing at a supernatural pace to provide the Darkness with a suitable host. This resulted in Dean’s last significant love interest – adults Amara and Dean were strangely attracted to each other. The will-they/won’t-they couple danced around their mutual magnetismplaying with a common theme in Supernatural – forbidden love. In the end, not even the powerful Amara could hold Dean back, proving that his true love was his family.