Despite being a show about hunting monsters, Sam and Dean Winchester had many romantic relationships in Supernatural over the years. Journeying across the United States and defeating numerous supernatural beings often meant the Winchester brothers encountered some interesting characters on their travels, and some caught their eye more than others. With a known reputation for being a ladies man, Dean Winchesters various flings were a persistent Supernatural trope that happened in almost every episode, and Sam was often left on the sidelines.
