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, 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.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.Officer 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.Anna
A fallen Angel, Anna and Dean had a lot in common and found themselves thrown together when they find out that they may be about to die. In the end, Anna took back her Grace and ascended back to heaven.