The love of Sam's life. They had been together for over a year when Dean suddenly arrived in their apartment and dragged Sam off to hunt a woman in white. When Sam got back, he discovered Jess on the ceiling in flames - exactly the same way his mother had died 22 years earlier. Even after her death, Sam still loves her, although he is finally realising that he needs to move on.Lori Sorensen
The daughter of a local reverend, Lori was having problems reconciling her faith with her desire to be a normal teenage girl. She was attracted to Sam and the feelings were mutual, even resulting in a kiss between them. However, Sam hadn't gotten over Jessica yet and pulled away from her.Meg Masters
The first time Sam and Meg met, they were both trying to make their way to California. They spent some time waiting at the bus station and got to know each other pretty well. However, the second time they met, Sam realised that something was unusual about her - just before she tried to have him and Dean killed by demons that she was controlling. Despite her psychotic tendancies, she was very attracted to Sam and seemed to want to try and get together with him.Sarah Blake
The daughter of an auction house owner, Sarah got involved with Sam when he tried to use her to get information about a haunted painting. Before he knew it, he realised he was attracted to her but didn't want to get close in case she got hurt. She reminded him that it was her choice and she helped out on a ghost hunting mission. When Sam and Dean had to leave, Sam finally made his move and kissed her.Madison Owens
As soon as Madison and Sam meet, there is a clear attraction between them, but it isn't until they believe her clear of the werewolf curse that she and Sam finally get together. However, the devestating truth is that she is still cursed and in their final, tragic moments together, Madison begs Sam to kill her in order to prevent her from killing anyone else - something he ends up doing, no matter how much it hurts him.Bela Talbot
Whether it was just a one-off dream or not, Sam seems to have a very sexual interest in Bela Talbot.Ruby
While Dean was in Hell, Ruby stuck close to Sam, training him in the use of his abilities. They eventually became lovers.