Jensen Ackles as Dean Winchester in purgatory on Supernatural.
Across its 15 seasons, Supernatural gave 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 of Supernatural season 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.
Related 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. 5 Jo Harvelle Seasons 2, 5, & 7 Close ✕ Remove Ads One of the longest-running recurring characters on Supernatural, 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 is a popular head canon in the Supernatural fandom that feelings existed between Dean and Castiel, but this pairing never became explicit. 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. Although Supernatural's deepening concern with Heaven and Hell wasn't popular with everyone, creating a degree of convolution, it rendered Supernatural a consummate long-term fantasy story with its own lore.
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