Annie was a fellow hunter with whom Bobby Singer was sexually involved, thus making her the only known lover of Bobby. Coincidentally, Annie was also involved with Sam and Dean.
During an investigation into a haunted house, Annie was killed before Sam and Dean could save her. Despite this, Annie's ghost remained, determined to solve the case, and did this with the help of Bobby, who was also a ghost. After successfully solving the case, Annie was cremated and went to Heaven, where Bobby would eventually follow.
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.
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.
Later on, Bobby discovered that Eleanor was not human, but a creature from Purgatory. When Bobby informed her of his discovery, Eleanor revealed herself to be approximately 900 years old. Knowing Castiel and Crowley were looking for creatures from Purgatory, Bobby offered to protect Eleanor, but Eleanor refused, believing she could protect herself.
However, Castiel came soon after Bobby left her house, and Castiel tortured her extensively alongside Crowley. Once she confessed how to open Purgatory, they set her free. Bobby found a dying Eleanor who passed on what she told Castiel. She died in Bobby's arms.
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.
Of the many hunters with whom Bobby is acquaintances with, Garth is the one Sam and Dean become closest to. Garth is a less-than-intelligent hunter who sought Bobby out for information. In their only onscreen interaction with each other, Bobby berates Garth for mixing him up with the real FBI, and questions how Garth is still alive.
Upon Bobby's death, Garth honors his hard work by donning a hat like Bobby's and taking up Bobby's job as a supplier of information for hunters. He also assists Sam and Dean in a few cases.
As a resident of Heaven, Bobby was under the protection of the angels, but after Sam Winchester requested help in getting Castiel into Heaven, Bobby broke a rule and escaped his own paradise. He emerged in a hallway leading to all the other Robert Singers who ever existed. He opened the door to each one to cause the residents to come out.
Hannah was alerted, and mortified, over his actions and she ordered one angel to locate the culprit. Hannah and the other angels struggled to get the Robert Singers under control while Bobby took this opportunity to sneak away and find the door which led to Earth. Bobby helped Castiel infiltrate Heaven and snatch Metatron from his cell, since he was believed to know the cure to the Mark of Cain currently infesting Dean's arm. Bobby then passed a note onto Sam through Castiel and bid the angel farewell.
Once back inside his paradise, Hannah and two angel approached him, ready to serve him punishment for his crime. It is still unknown what became of him, even after Hannah's death.
Bobby became an acquaintance of this hunting couple at an unknown point. After the Devil's Gate was opened, Bobby went on a hunt for the demons who had escaped from Hell with Sam and Dean, during which the trio encountered Isaac and Tamara.
The couple professed their desire to hunt alone, while simultaneously blaming Sam and Dean for the increase in demons on Earth. The group end up confronting the Seven Deadly Sins, one of who, Gluttony, manages to manipulate Isaac into killing himself.
Wrath then possesses Isaac's corpse into order to torment Tamara. Bobby tries to calm her down but she inevitably breaks the salt line keeping the demons out of the house the hunters are in. Fortunately, she is aware the demon is not Isaac and proceeds to kill him with a stake.
Following the skirmish, Bobby bids Tamara farewell, asking her to be careful. Tamara tells Bobby to be careful to before leaving.
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 John became acquaintances at an unknown point in time, though likely after Mary was killed and John discovered the hunting world. When Dean was only a child, John began leaving him and Sam with Bobby to take care of.
Prior to the beginning of the series, Bobby and John had a falling out with Bobby threatening to shoot John dead. They are never shown interacting, though Bobby does seem willing to forgive John for his offense.
Other than their shared reason to become hunters (murdered wives), Bobby and John are also the namesake for a baby shapeshifter Bobby John, due to them being father figures to Sam and Dean.
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.
Marcy is Bobby's neighbor who had a crush on him. She decided to visit him in Weekend at Bobby's by bringing him a peach cobbler, and pretend that her wood chipper was broken so he would come over to her house.
Unfortunately, Marcy arrived at a bad time, when Bobby was dealing with an Okami Rufus had failed to kill. The creature managed to get to Marcy, but Bobby succeeded in killing it in time, and stuffed it through Marcy's wood chipper, causing her to get covered in blood.
Marcy promptly lost all interest in growing close to Bobby. Bobby remarked this rejection with the words, "Story of my life".
While hunting down a shapeshifter, Bobby discovered that said shapeshifter had fathered a child named Olivia. However, the mother, a rich heiress named Bunny LaCroix, begged him to spare the girl. Bobby agreed, on the grounds that Bunny kept the child locked up in the attic for everyone's safety. He also offered to be there for Olivia should anything happen to Bunny.
Bunny kept her promise and took care of Olivia while keeping her hidden from the world. Unfortunately, Bobby died a couple of years before Bunny did, and the responsibility was passed down to his closest kin, who were Sam and Dean Winchester. The brothers initially thought Bobby had inherited something valuable, only to discover it was a key to Olivia's attic.
Olivia herself, angry at her mother's disrespectful and greedy relatives, began killing each one. Since Bobby had murdered her father and had chosen to spare her rather than kill her, and thus forcing her to live in seclusion for many years, Olivia sought to kill Bobby too, or Sam and Dean, who were the next best thing. Her plan was foiled when Dean shot her with silver bullets, multiple times.
Had Bobby managed to adopt Olivia, she would have been his third adopted child apart from Sam and Dean. Bobby's willingness to spare Olivia also demonstrated a more sympathetic heart, similar to Sam.
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 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.
Also Check OutEdit
Bobby and Castiel - Bobby and Castiel's relationship.
Dean and Bobby - Bobby and Dean's relationship.
Crowley and Bobby - Bobby and Crowley's relationship.
Sam and Bobby - Bobby and Sam's relationship.