Supernatural
Across its 15 seasons,Supernaturalgave Dean Winchester many love interests.
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.
Whether Dean or other characters,Supernaturalhad some great romancesthrough the years.
But through it all, Dean’s most important long-term relationship was with his beloved little brother, Sam.
Supernaturalseason 1, episode 12, “Faith,” aired on January 17, 2006.
Layla and her mother were Christian visitors of Roy le Grange, aSupernaturalseason 1 faith healer.
7Cassie Robinson
Cassie was a truly excellent match for Dean Winchester.
InSupernaturalseason 1, Cassie presented a far better match than Layla ever had.
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.
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.
Supernaturalseason 1showed Dean reigniting his old flame, Cassie, in episode 13.
Unlike Layla and Cassie,Carmen wasn’t even real.
Unfortunately for Dean, she was just a figment of his imagination.
This is one of the iconicSupernaturalepisodes that referencedBuffy the Vampire Slayer, one of Eric Kripke’s key influences.
But not even Carmen could dissuade Dean from hunting.
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.
If it hadn’t, viewers would forever be wondering which female hunter could rescue Dean from loneliness.
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.
The ending of Dean’s relationship with Lisa and Ben was one of the most heartbreaking things aboutSupernatural.
Therefore, he asked the angel Castiel to remove their memories of him.
Dean’s sacrifice would make itself apparent again and again, heartrendingly.
Nonetheless, Dean’s fascination with Anna led to a brief but passionate relationship.
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.
Dean’s father moved the family away, leaving Dean to break up with Robin.
“Bad Boys” was theSupernaturalseason 9 episode to show Dean’s clumsy first attempts at romance with Robin.
In general,Supernaturalwas always adept at showing the loneliness of life on the road.
