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. However, that didn't stop him from engaging in flings and one-night stands off-screen, earning himself his reputation. Whether Dean or other characters, Supernatural had some great romances through the years.

Eric Kripke's critically acclaimed TV show put hunter Sam Winchester and his brother, Dean, into dangerous situations with various monsters and their family business didn't help Sam and Dean develop long-term relationships. This was a theme throughout the show, which dived into the interpersonal difficulties that came with traveling across the U.S. to save people from demons,...