The very first scene we ever saw in Supernatural showed the love between the Winchester family and the loss that John, Dean and Sam had to cope with. This section is dedicated to all those who were loved and lost by the boys...

John

Mary Winchester
His wife, and the mother of his two sons, we can assume that Mary was the love of his life. Obviously very much in love with each other, her death almost led to John suffering a complete breakdown. He recovered though, thanks to his boys, but it is his love for Mary that started him on his journey of vengeance.

Ellen Harvelle
It's unclear whether Ellen and John were ever in a romantic relationship, but Dean and Sam have certainly considered the possibility. However, whether there was anything between them or not, Ellen still holds John responsible for the death of her husband.

Dean

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, 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.

Sam

Jessica Moore
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.