Bobby's Relationships

The relationships Bobby has had in his life other than Sam and Dean Winchester.

Karen Singer
They were a married and normal couple. Three days before Karen got possessed by a demon and Bobby was forced to kill her, the two had a fight about having children. After this incident, it drove Bobby to become a hunter and he now knows how to exorcise a demon. Bobby admits to himself in Death's Door, he would have lied to make her happy and he regrets that fight. He also still regrets killing his wife. In Dead Men Don't Wear Plaid, Death brings Bobby's wife back. He is happy to see her and protects her fiercely. Karen also protects Bobby, by not telling him that she remembers him killing her. In the end though, she does tell him and asks Bobby to kill her again. Bobby does so. Saying that she was the love of his life and the fact that he has had to kill her twice, kills him inside.

Rufus Turner
Bobby and Rufus have known each other for many years. Rufus was also the one to introduce Bobby to the hunting world. At some point, the two stopped talking after Bobby messed up a case and got someone killed.

In ...And Then There Were None, Rufus calls Bobby to tell him he has information on Bela Talbot. After that, Rufus leaves semi-retirement and the two resume working together.

In Weekend at Bobby's, Rufus helps Bobby get his soul back from Crowley by obtaining Gavin MacLeod's ring. Rufus also joins Bobby in investigating the Khan worm, however, the creature possesses Bobby and kills Rufus.

It is Rufus's death that drives Bobby to go after the Mother of All. During the events of Death's Door, while Bobby is in a coma, Bobby turns to Rufus for help in dealing with the reaper.

Ellen Harvelle
Their relationship was a friendly one. They worked together on closing the Devil's Gate, after Ellen showed up at Bobby's house. It is unknown how long they have known each other but they have probably been friends for a long time through the Roadhouse. When Ellen dies, Bobby grieves her death with Sam and Dean. Their relationship turned romantic when Balthazar saved the Titanic in My Heart Will Go On. In this alternative universe, he and Ellen are married. She is able to pull him out of his depression after Rufus's death. It seems they are very much in love. Bobby is shocked to hear that if they right history, Ellen dies. History does get righted, and they are no longer married. Bobby doesn't even remember being married to her.

Jody Mills
Bobby and Jody have a history together. Jody has been arresting Bobby for many years due to her being the town's sheriff. She didn't find out about his real job until her son become a zombie, and later saved his life. In Weekend At Bobby's, Jody helps Bobby get rid of the FBI. Bobby later asks her to get Rufus out of jail for him despite how this might risk her job. At first she refuses, but does it anyway. In Hello Cruel World, Jody calls Bobby for help when she notices her doctor is a monster. She later thanks Bobby by showing up at his cabin and cooks and cleans for him. The Leviathan reveals that Bobby does have some romantic feelings for Jody, but is afraid to show it. Later on Bobby kisses her for helping him figure out how to hurt the Leviathans. Jody later tells Sam and Dean that she's sorry that he died.

Bobby and his Family
Bobby didn't have a good past with his family. It wasn't mentioned much throughout the show, until Death's Door. Bobby and his father didn't get along much. When Bobby was younger, he was afraid of his father, and was constantly beaten by him. Bobby's mother simply took it. Bobby's father kept telling Bobby that he broke everything he touched, and this sticks with Bobby for a while. One day when his father hits his mother, Bobby gets a rifle and shoots his father dead. His mother is shocked and tells Bobby God will punish him. This is when Bobby learns that sometimes people won't thank you for saving them. Because of what happened with his father, Bobby never had children. When Bobby revisits the memory, he yells at his father for being a jackass, and that Bobby himself managed to adopt two great kids who grew up to be heroes.

Dick Roman
Bobby was forced to face the Leviathans and their leader, Dick Roman, after they escaped from Purgatory, despite the Winchesters and Bobby's combined efforts to stop them.

Unlike previous Big Bads, Bobby was in direct conflict with this new enemy, as not only did one of them destroy Bobby's house, Bobby was also forced to flee and hide. Through interrogating Chet, Bobby discovered the Leviathans' weakness to borax.

While checking out a factory controlled by Leviathans, Bobby gets captured and brought to Dick. Bobby tried to make an escape, taking things from Dick's desk. Sam and Dean prepare a vehicle for him, but Bobby doesn't make it in time before Dick shoots him fatally in head.

Bobby ultimately dies from his wound, but decides to remain as a spirit in order to try and stop the Leviathans. The sight of Dick however, throws Bobby into a rage and he attacks the Leviathan until Dean and Sam stop him. Bobby departs shortly before Dick himself is killed.

Also Check Out
Bobby and Castiel - Bobby and Castiel's relationship.

Dean and Bobby - Bobby and Dean's relationship.

Sam and Bobby - Bobby and Sam's relationship.