Throughout all 15 seasons of Supernatural, the Winchester brothers have encountered various romantic interests, ranging from angels and demons to the embodiment of darkness itself. However, not all of these relationships proved to be for the best. Due to the nature of their lives and careers, relationships only added complications for the Winchesters. Constantly on the move, finding someone who understood their unique situation was challenging.

Moreover, forming romantic connections through their work often proved to be risky. Dean Winchester was known as the flirtatious one among the brothers.

In the early seasons, he would pursue a different woman in every town they visited. However, as the show progressed, Dean started to form genuine relationships, some of which may not have been wise choices. One of Dean's former girlfriends was Cassie Robinson.

They had been together for a while, but Cassie was unaware of Dean's true profession. When Dean finally confided in her about his hunting activities, she dismissed it as a poor excuse for his frequent disappearances and broke up with him. It was only after her father was killed by a spirit that she believed Dean. They briefly rekindled their relationship before Dean returned to hunting with Sam.

Cassie's lack of belief in the supernatural and her trust issues with Dean made it clear that maybe they weren't a good match.

Another potential love interest for Dean was Robin, his first girlfriend at the age of 16. They were deeply in love and shared their dreams and fears with each other. However, Dean had to abruptly leave with his father before the school dance they had planned on attending, leaving them both heartbroken. When they met again years later, Robin believed Dean's stories and wished him well, even giving him a final kiss.

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