Dean's Relationships

Dean's Here are people that the Deab winchester had a strong connection with or love through out the show

Cassie Robinson

Dean first met Cassie in Athens,

Ohio, where she was at college and he was on a hunting mission. They dated a few times and became close enough for Dean to trust her with his biggest secret - what he did for a living. Confused and slightly freaked out, she ended their relationship, despite still being in love with him. When her father was killed, she contacted Dean for help and they eventually renewed their relationship by sleeping togther, although Dean soon left town again

Layla Rourke

Dying from an inoperable brain tumour,

Layla and her mother were frequent visitors to Roy Le Grange's church in the hope that he would heal her. She met Dean and formed a friendship with him after he was healed, but Dean and Sam had to stop the 'miraculous' healings before Layla was cured. Had their situations been different, there was a chance of a relationship between the two.

Hailey Collins There was a little connection between her and dean throughout the Wendigo episode there were both taken by the wendigo .Hailey even kiss Dean on the cheek before she takes her older brother Tommey to the hospital and told him thats she hopes he finds his father

Andrea Barr Widowed mother of Lucas, Andrea seems immune to Dean's charms when they first meet, even shooting him down when he tries a chat-up line on her. However, by the time he and Sam leave the area, she clearly starts to realise the attraction between them.

Kathleen Hudak Okay, so not actually a love interest, but there was clearly a friendship link between them, and with Dean being Dean, he did his best to flirt regardless!

Jo Harvelle Despite the age difference, Jo clearly has a crush on Dean, although it could be more to do wth the fact that he is a hunter than anything else. He has flirted with her in the past, but realised that it might not be a good idea.

Carmen Porter In Dean's fantasy world, Carmen was his live-in girlfriend. In the real world, she was a model in a magazine.

Lisa Braeden Dean had a fling with her once that he refers to as the "bendiest weekend" of his life. Almost 9 years later and there is still a spark between them. Lisa has a son named Ben who she says is not Dean's, but the child bears a striking resemblance to Dean.

Bela Talbot Dean meets her during the thrid season