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 that 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, due to not wanting to be like his own father. When Bobby revisits the memory, he yells at his father for being a monster, and that Bobby himself is better as he 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 alternate 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.
Bobby's late son who was taken by angels. Bobby and his son fought together against the angels and worked well together. Bobby stated he was unsure of how to be a parent but treated Daniel like his work and wanted what was best for him. In Nightmare Logic, while under the influence of Djinn poisoning he encountered an manifestation of his son that blamed him for his fate and nearly killed him until Mary intervened. Bobby had to kill the manifestation to save Mary.
Due to the angels war of extermination upon humanity and the destruction that they have wrought, Bobby hates them with a passion. Bobby's hatred goes so far as he has made it his hobby and his passion to kill any angels that he can find. The angels betrayal of humanity when they were expected to be humanity's saviors after the rise of Lucifer and his demons has left Bobby bitter towards them as well. Due to this betrayal, Bobby is inclined to be prejudiced towards angels and anything related to them on sight, showing a belief that it was only a matter of time before one turned on them. Just learning that Jack was a Nephilim triggered his hatred and distrust to the point that he accused Mary Winchester of betraying him by bringing Jack into his colony.
In All Along the Watchtower, while investigating the rift to the Main Universe, Bobby saved Castiel from a Tempter Demon. Despite his general hatred and distrust for angels, Bobby recognized that Castiel was different and not only spared him, but explained the history of his world to Castiel. Bobby later showed no signs of aggression towards Castiel and Castiel went so far as to call Bobby a friend to the Winchesters. They met again in Exodus when Castiel and the others returned, there was interaction between them but they evacuated the colony with the Winchesters and made it to the main universe.
While the full extent of Bobby's relationship with his world Mary Campbell is unknown, he clearly admires and respects her even after death. Bobby knew Mary well enough to know about her rejected deal with Azazel and her life of regret as a result. Bobby told Mary Winchester that Mary Campbell had saved his life "more than a few times" and even with her dead, he felt it would be wrong not to return the favor by protecting her Main Universe counterpart. Even ten years after her death, Bobby still expressed fondness for Mary Campbell.
In Good Intentions, upon first meeting Jack, Bobby threatened him until he realized that Jack was with Mary Winchester. After Mary called Jack a "friend of the family," Bobby decided that it was good enough for him and let Jack into his colony without further question. While at first amused by Jack's antics to entertain the young children, Bobby's interest was drawn by Jack's use of power to aid in his antics. Upon learning that Jack was a Nephilim, Bobby's hatred and distrust for angels caused him to immediately turn on Jack, believing that it would only be a matter of time before Jack betrayed them. Bobby effectively ordered Jack exiled for being a Nephilim.
After Zachariah and his angels began attacking the colony, Bobby angrily blamed Jack and his use of powers on how they were found. Despite Jack honestly not intending to bring the angels down on them, Bobby rejected his assertions and Jack's help as he felt that Jack had done enough damage. During the attack, Bobby witnessed Jack killing Zachariah to save Mary and was shocked but recovered in time to direct Jack to three more incoming angels.
After Jack helped to save the colony, Bobby changed his mind about the boy and warmly thanked Jack for what he did. Bobby listened as Jack explained that he knew Sam and Dean would've stayed to fight and he was going to kill Michael to protect Bobby and his people. Bobby was surprised to hear Jack's assertion about killing Michael to help them.
Bobby now works closely with Jack as part of the resistance against the angels and Michael.
Bobby has taken to training him in fighting after Lucifer took his powers.
Sam and Dean Winchester
Due to Sam and Dean not existing in the Apocalypse World, Bobby had never met them before they crossed over from the Main Universe in All Along the Watchtower. When the Winchesters arrived and recognized Bobby, he was mainly confused by their recognition of him, but explained the state of his world to the Winchesters and leant them Rufus to battle Lucifer with. Dean would later claim to Lucifer that he had a bet with Bobby, their "new, old friend," on whether or not the gun and its angel-killing bullets would work on an archangel.
In Good Intentions, while talking with Mary Winchester, Bobby expresses a level of fondness for Sam and Dean similar to the Main Universe Bobby. Bobby tells Mary that he feels she did good with them and explains how they weren't even in Apocalypse World five minutes before they tried to get Bobby to go home with them. However, Bobby refused as he felt his place was in Apocalypse World. Bobby also referred to the Winchesters as "the daytrippers."
They met again in Exodus, the three shared a drink and jokes about Bobby's counterpart. Bobby was skeptical of the plan to evacuate the colony to the main universe but later decided to join them in doing so.
In Let the Good Times Roll, Bobby was taught by them in getting accustomed to their world. Bobby has shown to care for them, since he was worried about Dean now being Michael's vessel.
In Good Intentions, after encountering Mary, Bobby initially took her to be the ghost of Mary Campbell before learning the truth. Bobby took Mary in, both because she was human and because he felt he owed Mary Campbell. While in his colony, Bobby shared a drink with Mary and discussed her alternate self, giving Mary his perspective on Sam and Dean and her decision to make a deal with Azazel, something that clearly put her mind at ease.
After discovering that Jack was a Nephilim, Bobby's hatred towards angels and anything connected to them caused him to immediately turn on Mary and accuse her of betraying his trust. Even after Mary warned that if Jack had to leave, she would have to as well, Bobby didn't change his mind and simply stated it was her choice. Despite blaming Jack for bringing the angels down upon them, Bobby had no trouble working with Mary and attempted to aid her against Zachariah before he saw that Jack was taking care of it. After Jack helped to save his colony, Bobby fully reconciled with Mary.
During Let the Good Times Roll, the two walk together and share a talk with bobby remarking he may want to stay in the new universe even if it would take time to adjust. Mary relates to this and they laugh. The two are shocked by Lucifer's return and Michael's attack but work together to avoid trouble.
As seen in Stranger in a Strange Land, the two are shown spending more time together and laughing with each other over cases.
In Gods and Monsters, she is amused by his outdated use of speech when on a case as he is embarrassed. When attacked by Michael's enhanced werewolves, she saved Bobby from being attacked by one before they locate Dean who was freed of possession.
During Nightmare Logic, they are on a case to find one of their fellow hunters. Sam noticed the attraction that the pair obviously had and Mary confirmed she does have feelings for him though is unsure since he is keeping her at arms length. Sam also told her that Bobby may have experienced a loss like the original Bobby and she hoped that he'd tell her. Much later, she saves him from a manifestation of his son and he worried as she was overpowered but stepped in to save her. Once the case was over and the group returned to the bunker, Bobby had his injuries treated. True to Sam's prediction, Bobby opened up and relayed to Mary of his hardships with losing his family and the stress of fighting for a decade. After he stated he saw no other way of his fate, Mary told Bobby there is another. Bobby decided to spend his recovery time with Mary at the cabin of Donna Hanscum.
The people of Apocalypse World
|“||Mary, your world has your boys. This place? I'm pretty much all it's got.||”|
Following the Apocalypse, Bobby set himself up as a leader to the surviving human population of the world, forming one of the last human colonies on the planet. Bobby expressed to Mary Winchester that he felt that while the Main Universe had Sam and Dean to protect it, the people of Apocalypse World only had Bobby. To this end, Bobby rejected an offer to come to the Main Universe which he knew was a far better place than his own world as it meant leaving the people of Apocalypse World without his protection. Bobby was shown to care greatly for those under his protection, taking the time to comfort someone injured in the angel attack.
Also Check Out
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.