Dean didn’t deserve his reputation as a “ladies’ man” inSupernatural, and there is one stat that proves it. Despite some 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.
Sam Love Interests
Dean Love Interests
Jessica Moore
Lori Sorensen
Sarah Blake
Madison
Ruby
Dr Cara Roberts
Sparrow Jennings
Lana
Piper
Becky Rosen
Amy Pond
Amelia Richardson
Eileen Leahy
Velma Dinkley
Anna Milton
Cassie Robinson
Carmen Porter
Layla Rourke
Robin
Lisa Braeden
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 Supernaturaland 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 passed.
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 offscreen. A consistent Supernatural trope that happened almost every episode was Dean’s one-off hookups, while Sam researched the case they were working on.
Supernatural had its highs and its lows over the 15-season run, but some episodes stood out among the 327 total as the best of the best.
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.
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.
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