Why are you the way that you are? Honestly every time I try to do something fun or exciting, you make it not that way. I hate so much about the things that you choose to be
  -Michael revealing why he hates Toby. ("Casino Night")

The Michael-Toby Relationship refers to one of the most recurring gags on The Office  in which Michael Scott expresses his intense hatred for HR representative Toby Flenderson whenever he interferes with his unethical work antics. Michael's hatred of Toby lasts from Season 1 to Season 7 of the series and only ends when he departs for Colorado in Goodbye Michael.


Michael intensely despises Toby because, according to Michael, his job was to "make the office fun, while [Toby's] job is to make the office lame". Michael's often-successful self-delusions that he is the life of the party frequently have a light shined on them by Toby's interactions with him. This is usually not Toby's intention, but his inability to go along with Michael's vibe is like a mirror being held up to Michael. It shows him the truth that he is constantly hiding from. In their bitter relationship, Michael is clearly the antagonist and Toby the victim. Michael seems to be completely blind to how harsh his treatment of Toby is and claims that Toby is the bad guy and that he tortures him (he points this out to Holly in "Goodbye Toby"), completely ignoring that he verbally puts Toby down on a daily basis while the latter simply does his job and voices his own opinion and attempts to dissuade Michael from ideas that are truly reckless and impulsive and unethical in the office. Even on occasions where Toby offers kindness to Michael such as in "The Deposition" and "Niagara", Michael shows nothing but rudeness and hatred.

Michael views Toby as his sworn enemy and takes every opportunity to demean him. As Michael sneers, "Toby is in HR, which technically means he works for corporate, so he's really not a part of our family. Also, he's divorced, so he's really not a part of his family" and says that "Toby Flenderson is everything that is wrong with the paper industry." He also stated, "I hate so much about the things that you choose to be". At various times, Michael has referred to Toby as "the worst human being ever," a "convicted rapist," "evil snail," "animal rapist," "Satan" and "the Antichrist." Michael once says that if he "had a gun with two bullets and was in a room with Hitler, Osama Bin Ladin and Toby, he would shoot Toby twice." Michael has physically hurt Toby on a few occasions as well such as throwing a pen at his forehead and checking him while skating.

Michael frequently threatened to fire Toby, which he could not do because Toby is not considered a local branch employee, having been hired by the corporate office and then assigned to Scranton. The majority of Michael's techniques that are questionable bring Toby by his own obligation to confront Michael about how corporate would like him to do his job. Ultimately Toby and Michael represent the conflict between employees and upper management. While Toby is mainly a passive victim to Michael's abuse who tries his best to remain calm, Toby himself has shown on a few occasions in the series that he enjoys seeing Michael in misery such as in "The Injury" when Michael injures his foot and collapses and struggles in the restroom (where Michael is disgusted by the idea of Toby helping him instead of Ryan, and Toby gets to mock Michael's wimpiness and notes with disdain "you only grilled your foot") and when Toby viciously beats Michael in a game of poker, in which he says he will chase the feeling of taking Michael's money (Casino Night). Toby has also laughed at Michael's misfortune on occasion such as in "The Deposition" when Toby learns that Michael thinks Ryan is hot and also in "Koi Pond" when he learns Michael has fallen into two fountains. Toby once even instructed Pam on how to hit Michael harder after he gave her the opportunity to do so for dating and dumping her mother, showing that he enjoys seeing Michael suffer to a degree (Double Date). Toby has on occasion stood up to Michael such as in "Classy Christmas" when Michael tries to accuse Toby of destroying Holly's beloved Woody doll to which Toby immediately responds that the vandalism is something that Michael would do, to which everyone agrees.

Toby seems to have a strong ability to absorb Michael's abuse as seen in "Goodbye Toby" where he is given a potential opportunity to complain about Michael's antics and after Michael threatens to kill him (though he does so in a situation where Holly and Pam would be able to listen to Toby's issues if he wanted to present them, as they either don't know how awful Michael has been to him or, in Pam's case, know it very well), Toby claims that everything in the office is fine, and later shrugs to the camera that he has survived Michael's abuse long enough and that disclosing it is pointless. Toby has never attempted in any way to get Michael punished for his harsh treatment of him (despite having the power to do so) and has never gotten angry with him for unknown reasons. This stands in direct contrast to other members of the Office who get angered at Michael for his stupidity and rudeness such as Jim, Pam and notably Stanley. Toby also somewhat seems to be in denial that Michael hates him as seen in "New Guys" in which after shooting down his impulsive idea, Andy says to Toby: "Now I know why Michael hated you so much," to which Toby responds "No, he didn't", possibly signifying that Toby does not view Michael's abuse as hatred.

Toby seems to want Michael's friendship but is too shy to talk to him about it. In "The Lover" Michael opens up to Toby, asking him to keep Pam under control, by giving Toby a hug and calling him a "good guy." Toby says that he is delighted and "Michael would like me once he got to know me," but as soon as Toby fails to keep Pam under control, Michael starts to hate him again. Michael, though, ended up being appreciative of Toby's efforts to actually help him during their Sabre-mandated counseling sessions (even if he spent much of the time hurling harsh statements at the HR rep), to the point where he decided to talk to Toby instead of simply signing off on a few corrected forms at the sessions' end. While in "Take Your Daughter to Work Day," Michael ends up bonding with Toby's daughter Sasha when the employees bring their children into the office. However, later on, Michael becomes withdrawn and sad that he hasn't had any children, which Toby senses and ends up being confidant to Michael. Michael inquires about being Sasha's godfather. Toby simply tells him that she already has one. Michael has on a few occasions realized when his mistreatment of Toby has gone too far such as in "Women's Appreciation" in which he literally asked him to expose his genitals and also in "Frame Toby" after attempting to get Toby arrested and fired, possibly showing that Michael's hatred of Toby has limits.

In "Goodbye, Michael" when Michael wants to give everyone in the office a proper goodbye, he somewhat makes up for all the times he has berated and insulted Toby by listening to him without insulting him once, possibly showing that he will miss Toby somewhat. However, his face betrays both his difficulty in doing so and his horror when an appreciative Toby suggests that Michael look up Toby's brother Rory in Boulder once he's settled himself in Colorado. This can be viewed as Michael's final comeuppance for his treatment of Toby as even though he is moving away to Colorado, he will still not escape Toby and will have to endure annoyance from Toby's brother Rory (who seems to be virtually identical to him and whom Toby encourages to be friends with Michael).

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