Dean didn’t deserve his reputation as a “ladies’ man” in big changes happening throughout Supernatural’s seasons – many characters were introduced and killed off and the Winchesters both went to Hell at some point – the show stuck to a certain formula for most of the time. This includes Dean and Sam being on the road hunting strange creatures every week, which meant that romance was a less important theme in Supernatural.
Yet the Winchester brothers did have quite a few relationships over the years. As the older brother, Jensen Ackles’ Dean was always hailed as the “ladies’ man” due to his charismatic nature and constant flirting. On the other hand, Sam’s sensitive nature meant he didn’t pursue one-night stands as often, and any character with whom Sam did have a relationship often ended up dying; one of the many running tropes in Supernatural. However, surprisingly, Dean’s famous “ladies’ man” status is somewhat untrue when examining the actual statistics surrounding the Winchesters brothers' love interests in Supernatural.
Sam Winchester Actually Had More Love Interests Than Dean In Supernatural
Sam's Onscreen Relationships Depict Him As A Ladies' Man
Shockingly, Sam Winchester had more love interests than Dean in Supernatural, despite Dean’s status as a flirt. Sam had 14 onscreen love interests throughout Supernatural, and some of them were monsters. Following Jess’ death, Sam struggled to move on in season 1, and despite his budding feelings for love interests like Sarah Blake, Sam couldn’t commit so soon. In season 3, however, Sam began his first long-term relationship with Ruby, one of the worst mistakes Sam made in Supernatural. After a string of one-off flings, the next relationship was with Eileen Leahy, but she was unfortunately killed in season 12.
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Conversely, Dean Winchester only had six onscreen love interests throughout Supernatural, less than half of Sam’s. The first was Cassie in season 1’s widely disliked “Route 666,” who demonstrated a softer side to Dean’s character not previously seen in the season; Dean told Cassie about hunting, something highly frowned upon, showing his dedication to her. Lisa was a big love interest for Dean as she appeared more than once in Supernatural and helped Dean to get out of the hunting life while Sam was dead. This confirmed a weird trend of the Winchesters having the best romances when their brother has ed.
The Caveat Behind Dean Winchester's Reputation As A Ladies' Man In Supernatural
Dean Winchester Had Lots Of One-Night Stands Offscreen
The reason behind Dean’s reputation as a “ladies’ man,” despite onscreen evidence suggesting Sam is more worthy of the title, is that Dean had a more active sex life off-screen. A consistent Supernatural trope that happened almost every episode was Dean’s one-off hookups, while Sam researched the case they were working on. It's clear that Dean indulged his baser instincts, with several guilty pleasures like unhealthy fast food, beer, and pornography being among his most frequently seen pastimes, but that doesn't mean he was always chasing casual sexual encounters.
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Dean’s love interests aren’t always shown but are heavily implied or talked about a lot. Furthermore, Sam doesn’t usually partake in this kind of activity, so any romance storylines are highlighted as being “abnormal.” For that reason, Dean is considered more of a “ladies’ man” than Sam in Supernatural. But in reality Dean is a lot more careful with his heart than his brother. Sam falls hard and fast, resulting in ongoing relationships, but there was only ever one girl who really captured Dean Winchester's heart. And outside of that one relationship, Dean kept his feelings closed off to pretty much every other girl who expressed interest, though he did occasionally partake in one-night stands.
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Dean Winchester's Heart Only Had Room For One Girl
Meanwhile, there is only one romantic partner of Dean's who clearly stood apart from any of his other flings. Dean had a special connection with Lisa Braeden, a woman who is first introduced in Supernatural season 3, but even then, the show reveals that Dean had a long history with Lisa. When Dean meets Lisa in season 3, he meets her son, Ben, who is eight years old and bears a striking resemblance to Dean. Interestingly, Dean last met Lisa about nine years earlier, leading to some speculation on Dean's part that he could be the father.
Dean had a special connection with Lisa Braeden.
Lisa assured Dean that he was not in fact the father, but this didn't deter Dean from wanting to spend time with Lisa and her son. Dean visited Lisa and Ben again in season 5, and when Sam was trapped in the cage with Lucifer, Dean went to live with Lisa and Ben. However, when Sam returned, and Dean returned to his life as a hunter alongside his brother, he ultimately had to make a huge sacrifice to keep Lisa and Ben safe. After Lisa is captured and nearly killed by demons, Dean asks Castiel to remove any memory of himself from her mind. All in an effort to keep her and Ben safe.
Dean's Romantic History In Supernatural Proves He Really Wanted What Sam Eventually Got
This separation is devastating, and it's clear that his relationship with Lisa was something completely different to anything else on Supernatural, but the tragic ending made it impossible for Dean to enjoy a happily ever after. The thing is, as the older brother, Dean feels a huge burden of responsibility to protect and take care of his brother. If Sam was hurt, he immediately moved heaven and Earth to find a way to bring him back. The only reason he went to Lisa and Ben and lived with them for a year when Sam was trapped with Lucifer was because Sam made him promise to let him go and find peace.
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But outside that moment, Dean continued hunting because he wanted to protect others, like Lisa and Ben, and often he was the only one who could do it. When Lisa and Ben were no longer a part of his life, he resigned to being a hunter forever, because he didn't know anything else, and he had already lost the people that mattered most to him outside his brother, Sam. But, if Dean were given the opportunity to actually pursue a life like what Sam eventually had, he would have made a great father to Ben, and husband to his beloved Lisa in Supernatural.
Supernatural
- Release Date
- 2005 - 2020-00-00
- Network
- The CW
- Showrunner
- Eric Kripke
WHERE TO WATCH
Created by Eric Kripke, Supernatural is a fantasy/drama series that premiered in 2005. The series follows the adventures of Dean and Sam Winchester - two men wronged by supernatural beings as children who now spend their days investigating and hunting demons, ghosts, and monsters across the United States.
- Writers
- Eric Kripke, Andrew Dabb, Robert Berens
- Seasons
- 15
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