Toby Flenderson

Toby H. Flenderson is the human resources representative for the Scranton branch of paper distributor Dunder Mifflin/Sabre. Mild-mannered to the point of being physically incapable of voicing his opinions or asserting himself, Toby can be somewhat mournful about his life choices (he fell into the field of Human Resources after leaving his training at seminary in order to pursue the woman he would later marry and painfully divorce). He likes his colleagues, although he is sometimes exasperated by the excessively chatty Kelly Kapoor. He also has a long-standing crush on Pam Beesly, which he almost reveals at the end of Season 4 when he resigns from his position to move to Costa Rica. Toby was intensely despised by branch manager Michael Scott, largely because Michael had no authority over him as Toby reported to corporate headquarters, and because Toby frequently tried to dissuade Michael from many of his ill-conceived and impulsive ideas. Michael sums up his feelings for Toby in the episode "Casino Night", asking, "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." For Toby's going away party in "Goodbye Toby", Michael gives him as a gift a rock with a note attached reading "Suck on This!" Shortly after arriving in Costa Rica, Toby suffers a zip-line accident and midway through season 5, he returns to his old job at Dunder Mifflin, much to Michael's fury.

In his childhood, Toby was forced to testify against both of his parents when the two got divorced. He attended Bishop O'Hara High School and is a Penn State University alumnus. In the Season 5 episode "Casual Friday", a diploma at his cubicle reveals Toby also has a B.S. in psychology from California Coastal College. The Season 7 episode "Counseling" reveals he has a degree in social work from Temple University. Toby was in a seminary for a year but dropped out when he met his future wife. The two moved to Scranton and had a daughter named Sasha. They later divorced. Toby loves his daughter and went the extra mile in "Moroccan Christmas" to buy her one of Dwight's Princess Unicorn dolls from Darryl Philbin, noting that his ex-wife "will be so pissed" and that "for once, Daddy's going to be a hero." However Darryl bought an African-American doll. When Darryl asks if the doll is okay, Toby says "It's even better than the one I wanted."

Toby claims to have no "passion for HR" and was only hired at Dunder Mifflin as it was the first job he could find. He joins the others occasionally but only for business matters, such as reviewing the company's sexual harassment policy and mediating conflict between employees. Toby prefers to let angry employees vent to him, after which they feel better and the conflict eventually settles down and solves itself. This strategy worked virtually trouble-free for years until Michael Scott publicly reads off all listed complaints.

Toby tries (but usually fails) to enforce corporate policies and rules when Michael disregards them, typified by an incident in which he quashes Michael's plan to invite Boy Scouts to a Casino Night party:

Actually, I didn't think it was appropriate to invite children since it's, uh, you know...there's gambling and alcohol...and it's in our dangerous warehouse...it's a school night, and you know, uh... Hooters is catering. You know, is that not—is that enough? Should I keep going?

Toby usually avoids office activities whenever possible and, like most of the staff, only tolerates Michael. He has reached out to Michael several times despite Michael's continued abuse. He gets along with the rest of the staff. When Dwight approached Michael about missing a gift bag during "A Benihana Christmas", Michael suggested stealing it from Toby, much to Toby's later chagrin, as all the office staff had new robes except for him (Pam later gave her robe to Toby, and this increased Toby's unrequited crush on her). Michael on numerous occasions attempts to blame Toby for problems that are clearly his own fault such as in "The Merger" in which he questions Tony Gardner if he is quitting because of Toby. In "Classy Christmas" Michael vandalizes Holly's Woody doll (a gift from her boyfriend) and tries to convince her Toby did it. Toby denies it and says the vandalism is something Michael would do.

He seems to have plain bad luck in many instances and seems to accept this way of life as inescapable, which may be the cause of his sad disposition. On some occasions, Toby enjoys some rewards and good fortune, much to his satisfaction (and to Michael's annoyance).

Toby's favorite movies are Say Anything..., The Shining, Annie Hall, and Toy Story 2.[2] He also likes short stories, mystery novels, and "old hard-boiled detective" movies. One of his favorite TV shows is Damages.

He lived in Honolulu for a year and stated in "Branch Closing" that he would take severance from the closing, sell his house, and move to Costa Rica. In "Local Ad", it is revealed that he worked in advertising for three years before coming to Dunder Mifflin. According to a deleted scene from the episode "Launch Party", he is colorblind. Toby is also allergic to mushrooms ("Survivor Man").

Toby has an ongoing concern about the air quality at the office that borders on an obsession. He worked a recommendation that the air be tested into his goodbye toast in a deleted scene from "Goodbye, Toby;" he ignored the two factions that wanted to use an unexpected surplus for new chairs or a new copier and said the money should go to air testing; and he put together a meeting to discuss the radon testing kits he was dispersing in "The Chump."

Toby is seen as an awkward and quiet guy in the office. He is often passive when he is teased or when he gets picked on and does not appear to know how to stand up for himself. While members of the office have shown disgust at Michael's treatment of Toby, for unknown reasons, nobody has ever stood up for Toby when Michael insults him or excludes him from events, but he is generally liked in the office. The others possibly avoid standing up for him as Michael has authority over them (unlike Toby) and could potentially punish them for speaking up or possibly because they do not want to suffer the same treatment Toby suffers from Michael. Toby, however, has never asked anyone for help when Michael mistreats him, which is possibly the reason why no one ever stands up for him.

Besides Michael, the other staff members treat Toby with respect. For example, after Toby conducts a brief sexual harassment seminar, the staff is left in a good mood and laughing, until Michael comes in and takes over. Others have become annoyed with Toby occasionally, but overall he is well-respected and considered one of the more intelligent people in the office. His behavior does change somewhat when he meets Nellie (whom he develops a romance for), and he is shown to become somewhat of nuisance to her by being socially awkward and not handling his crush on her with any subtlety (and also an annoyance to Andy, though this is more of a Michael Scott-like situation where Andy gets angry and frustrated at Toby for doing his HR job at the expense of Andy's weirder/less legal ideas).

Toby only appears in a few episodes, showing up first in a scene in "Diversity Day", in which he jokes about sitting in an Indian Circle (to which everyone else laughs). Michael, having told many more offensive jokes, is offended by Toby's joke and tells him that "This is an environment of welcoming, and you should just get the hell out of here." Toby does so and the staff suddenly goes very quiet. This is the first instance in the relationship between the two, Toby trying to be responsible, and Michael trying to demean and undermine him as much as possible. In "Hot Girl", Toby is introduced by Michael to Katy the purse saleswoman; after Toby and Katy begin talking happily about their high school days, Michael deliberately humiliates Toby by mentioning his divorce and how he once briefly had to live in his car. He also notices the picture of Toby's daughter on his desk, and refers to her as "cute"; however, this is probably a further attempt to portray Toby, a divorced father, as undesirable.[4]

One of Toby's major appearances was in "Sexual Harassment", where he holds a sexual harassment meeting for the staff, only to be interrupted by Michael and a blow-up doll. Michael then states that everyone is still "generally quite happy", which he thinks is because Toby has not yet had the meeting. In fact, Toby did have the meeting and everyone clapped after he was done, leaving them in a good mood.

In a deleted scene of "Halloween", Toby tries to persuade Michael to make a decision as to which employee he must fire. When Michael chooses Toby, Toby replies that he does not report to Michael. When Michael then tries to get Toby to quit, Toby replies that someone else will just take his place. Michael then claims that if he had the authority, he would immediately fire Toby, to which Toby calmly replies, "I know, Michael."

In "Booze Cruise", Toby is late arriving at the dock for a company cruise. When Michael orders the ship to leave without him, Toby grins broadly, implying he had planned things in order to miss the event.

In "Take Your Daughter to Work Day", Toby's daughter, Sasha, distracts Michael; the two actually get along, showing Michael's friendly side. Toby and Michael have a good conversation about Michael's desire to have a family: Michael wants to have a biological child, and Toby hints that he should seek out alternatives. When Michael asks if Sasha already has a godfather, Toby quickly replies, "Yes."

"Conflict Resolution" is Toby's biggest role in the season. Toby shows that he handles inter-office complaints calmly and efficiently, only to see his work undone by Michael's stupidity. When Dwight threatens to quit unless Michael fires Jim (because of Jim's history of pranks against Dwight), Michael attempts to resolve the conflict by making vague promises of future action, an approach similar to one Toby had used successfully in the past. Toby covertly shows that he files Dwight's complaints against Jim in a trash box and that he puts the huge number of complaints against Michael in unmarked boxes that are filed into the vast space of the warehouse.

In "Casino Night", Toby tries to convince Michael not to invite Boy Scouts to a company Casino Night. Michael's response is to demean him in front of everybody. Toby just lets him finish. That night, however, Toby viciously beats Michael at no-limit Texas Hold 'Em, to Michael's visible irritation. Later, Toby says to the camera, "I'm not gonna lie—it felt good to take money from Michael. I'm gonna chase that feeling."[5]

In "The Convention", after finding out that Pam is no longer engaged, Toby makes a couple of attempts to ask her out but can't say the words. Michael trashes Toby to Jim and eagerly asks Jim if the HR rep is the reason he left for Stamford. Michael is visibly stung when Jim says no (he later tells Michael about his declaration of love for Pam).

In "The Convict", Michael jokingly refers to Toby as a rapist, much to the dismay of those present. Later, Toby convinces Michael to release the office employees from the conference room, whom he had locked in there as punishment for unfavorably comparing Dunder Mifflin to a prison.

In "A Benihana Christmas", Michael has Dwight take Toby's gift bag present of an expensive robe when they run out of enough of them for everyone. Pam later comes over and kindly gives her robe to Toby.

In "Back from Vacation", Toby asks Michael about the "Jamaica Jan Sun Princess" photo. Michael tries to accuse Toby of stealing the file from him, but Toby says "nine different people sent it to me, including my ex-wife, and, well, we don't talk." Michael then insults Toby's divorce again and calls him a perv, but does state for the record that he and Jan do not have a relationship.

In "Phyllis' Wedding", Toby is seen with a beautiful woman whom he says he met in the gym, although Kevin believes she is a paid escort. When Phyllis tosses her bouquet, it is Toby's date that catches it, and then excitedly runs back to Toby and the two share a brief embrace and kiss. Toby is then shown in a talking head as very ecstatic towards the outcome. It is implied that Toby and his date eventually broke up afterwards as this is the only episode where she is seen.

In "Business School", he tells Pam he cannot make it to her art show because his daughter has a play. He then offers to miss his daughter's play because "what they do is not art."

In "Cocktails", Toby spends the whole evening trying to win Pam a duck from a claw machine after she comments on how cute it is. When he finally wins it, Pam suggests that he give it to his daughter instead.

In "The Negotiation", Toby is forced to listen to Ryan and Kelly bickering nonstop when Michael moves Ryan back to the annex. Toby wonders if Michael did this to punish Toby and that if he did, it was a genius move. Toby goes with Michael and Darryl to New York after Jan says she will not do the contract negotiation unless Toby is there. When Michael repeatedly mentions his and Jan's relationship at that point, Toby takes notes and Michael insults him, but Toby just says he has "preparing for the deposition" that he thinks will inevitably occur because Michael threatened to withhold sex from a female superior in order to get a modest, scheduled raise, commenting, "It will be a groundbreaking case when it inevitably goes to trial." Additionally, when Darryl says he will stay in New York for the night, he tells Toby he can join him and stay at his relative's house, pointedly not extending the same offer to Michael.

In "Women's Appreciation", Toby is out of the office at a parent-teacher conference when Phyllis is flashed. When he returns, Michael scoffs at his alibi and seriously asks to see his penis to rule him out as a suspect. Toby turns towards Michael and looks like he has about to get angry; Michael then seems to catch himself and admits what he said to Toby was wrong.

In "Beach Games", Michael bans Toby from attending the beach event because he wants it to be fun and says it will not be if Toby is there. Toby is visibly upset that he will not get to see Pam in a bikini (which she ends up not wearing there) and is seen despondently doing paper work in a deleted scene from the episode.[6]

On the Season 3 DVD, Toby gives a series of wraparound interviews. Among other things:

• He lists the various insulting nicknames Michael has for him, including "The Devil's Butthole" and "Gargamel", noting "I prefer Toby".
• He describes Michael's "invention" of a safe George Foreman Grill after he burned his foot, which involved putting the Grill inside a bunny cage.
• He says that his job is not a nightmare because you wake up from nightmares; it's more like an unrelenting "daymare".
• He lists what he would do if he had one day to live, including wanting to "Burn this place (The Office) to the ground" this makes the interviewer react with horror and/or disbelief which Toby responds to with a confused "What?".
• He says, "HR isn't just a job, it's a way of life. (Pause) But I wish it was just a job."[7]

In "Fun Run", Toby goes against Michael's theory of an office curse by mentioning he won a drawing at a local pizza place, but Michael insults him and later ignores his statement that you cannot ask employees about their religions. Before the race, Dwight puts Imodium in Toby's drink instead of Ex-Lax and Michael pulls Toby's shorts down right before the starting gun is fired. Toby later wins the race to cure rabies, beating Michael and accomplishing something noteworthy; however, no one notices his win, and Kelly does not even bother looking up when he crosses the finish line. Toby then wonders why the 5K course was a straight line instead of a circle that would have returned everyone to the Dunder Mifflin building.

In "Dunder Mifflin Infinity", after seeing Pam kiss Jim, Toby sends out a memo about public displays of affection. When Michael accosts Toby about the memo (thinking it's about him and Jan having sex in the office), Toby tells him, in front of everyone, that it is about Jim and Pam. When they confirm that they are dating everyone is happy, except Toby. Later Pam and Jim visit him to see if they have to sign a "Love Contract", but he tells them to wait and see. In a scene that was added to the episode's repeat airing on NBC, Toby comes into work with a woman he says is his girlfriend and makes out with her right in front of the reception desk and Pam.

In "Money", Toby shows that he uses very good grammar when he corrects Michael and clears up a confusion between the usages of the words "whoever" and "whomever" ("who" is used as a subject, while "whom" is used as an object). Michael responds by telling Toby to shove a letter opener in his skull.

In a deleted scene of "Local Ad", Toby pitches an idea of having a stop motion ad that Michael, of course, puts down although the rest of the office seems to like the idea. When the local ad is being played at the bar, Toby is in the ad, but only briefly. While Michael was shooting the scene of the paper airplane flying out of the hand of Creed towards the conference room window, you see Toby in the conference room packing up whatever work he was finishing. Michael did not want Toby in the video; however, for a fleeting moment, Toby had managed to unintentionally get a part in the ad.

Toby's distaste for Pam's relationship with Jim is again brought up in "Branch Wars" when Jim is allowed to join "The Finer Things Club", an exclusive organization built up by Pam, Toby, and Oscar, dedicated to discussing civilized culture. During the episode's final scene, after Jim contributes his ideas on the book being discussed, Toby scrutinizes him very bitterly, hinting again at his disdain for Jim's success with Pam. His irritation is attributed to the fact that Jim did not read the book, though Oscar and even Pam are also annoyed with Jim's wisecracking, uninformed behavior. Also in this episode Michael tells Karen she can have Toby instead of Stanley; when Karen says Toby is not a salesperson, Michael briefly tries to talk up Toby's ability to learn before saying he cannot fake it and insulting the HR rep anew.

In the episode "Survivor Man", Toby ends up getting on Jim's nerves. When Jim is named Acting Manager while Michael is off on his "wilderness adventure" and starts altering the office's birthday schedule, Toby asks Jim if he can have a birthday celebration, explaining that Michael deliberately held a party for Toby at 4:58 PM on a Friday so no one would attend. Jim agrees but comments that he likes Toby but that the guy is really annoying him, claiming that sometimes Toby can sometimes be a little bit much. Jim's dismissive, disgusted attitude toward Toby (whom he has always gotten along with before) very closely mirrors how Michael treats Toby. It is not clear whether Jim is genuinely fed up with Toby or whether this interplay showed that Jim was beginning to act like Michael. It is also possible that Jim was not annoyed at Toby specifically but at the general reaction to his plan. Jim's disgusted attitude can also be attributed to the fact that Toby has been treating Jim fairly poorly in previous episodes due to his jealousy of his relationship with Pam.

Michael's hatred for Toby is brought up again in "The Deposition" when Michael says he does not want Toby in the deposition and nastily asks if the HR rep is there "to renew your divorce vows" (Toby is also sitting a conspicuous distance from Michael in the uncrowded room being used for the proceedings). When the two happen to sit next to each other at lunch, Toby kindly tells Michael that he can relate to Michael's situation, of Toby's parents' divorce. While Toby is talking, Michael pushes Toby's lunch tray on the floor, then gets up and leaves. Later in the episode, Toby begins to laugh at Michael after learning Michael thinks Ryan is "hot." Also, after Jan's attorney brings out Michael's diary, and the head of the deposition says "Okay, we'll need ten copies of that diary", to which Toby says, "Make that eleven." In a deleted scene, Michael asks Toby if he will tell Meredith that the car accident from Fun Run was Michael's fault, and Toby nods.

In the episode "Night Out", he puts his hand on Pam's leg and caresses it for a long, awkward moment, which everyone standing around seems to notice, making this the first time the employees see Toby's possible crush on Pam. Immediately thereafter, realizing what he had just done, he abruptly announces that he is moving to Costa Rica, runs outside to the security fence, scales it, and disappears into the night. This scene was done by a stunt double, as Lieberstein wanted to do it himself but it was decided for insurance reasons to let the stuntman do his work.

In "Did I Stutter?", Toby and Ryan together (who both have a problem with Jim; Toby dislikes him for dating Pam and Ryan dislikes him for going over his head) warn Jim on his job performance, citing specifically his indifference toward his job and use of time (namely "goofing off with Dwight" and "time spent at Reception" with Pam). Toby then says to the camera that Jim's time spent with Pam "has finally caught up to him", but he repeats Pam's name several times when unnecessary. Toby later says, though, that he agrees that Jim has good numbers but Ryan thinks they are not good enough. In the same episode, Toby convinces Michael he needs to deal with Stanley for his open insubordination during a staff meeting, though Michael goes about it a different way because Toby's method "did not work because it was stupid." Michael also says Toby does not have any friends, but Michael does so in the context of stating that Stanley is Michael's friend, which is later shown to be completely inaccurate as Stanley despises him for his stupidity and is not afraid to confront Michael about it. It is also shown that Dwight thinks Toby may be Jewish, as Dwight's org chart shows a blue Star of David with a question mark next to Toby's name; Toby did not say what (if any) religion he practiced when Michael prodded the staffers to talk about their religious practices in Fun Run. As Toby spent time in a seminary (as revealed in season five episode "Casual Friday") he is most likely a Roman Catholic.

In "Goodbye, Toby", he follows through on his earlier plans and quits his job as HR representative to move to Costa Rica. Michael is overjoyed at his departure and plans to throw a lavish goodbye party that reflects this. Both Kelly and Pam say they are sorry he is leaving, with Pam saying in an interview that she thinks he is kind of cute. Toby also ends up annoying Holly, his replacement, to a degree while showing her around the office and she is somewhat rude to him and claims that he almost bored her to sleep, something which Michael enjoys hearing (Holly remains oblivious that Michael, in fact, abuses Toby and Michael claims that Toby tortures him, though it is possible she only puts Toby down so as to get on Michael's good side). Toby faces a cruel exit interview from Michael but the tables are turned when Holly and Pam join the interview. Michael is unable to berate Toby at length as Holly takes over. When Toby is asked; "What would you improve about Dunder Mifflin?", Toby claims he has a few ideas. Realizing that Toby has a potential opportunity to reveal and complain about his unethical work behavior and abusive treatment, Michael hides his face and angrily glares at Toby and silently threatens to kill him if he answers the question. Toby does not seem afraid but simply gives a "things are OK as they are" answer. Toby later tells the camera that he has made it far enough without disclosing Michael's behavior and that there is no point in doing so.

Toby gets revenge when Michael's insulting farewell gift to him is exposed (a rock with a note reading: "Suck on this!") and Pam gets Michael to unwillingly give up his watch to Toby, which he does, clearly upset. Toby's main concern on his last day is getting pictures of himself alone with Pam, which he finally does as his party is ending. Michael gets a last dig in by having Hank the security guard escort Toby out of the office as he leaves for his new life in Costa Rica and is still shown to be upset when Toby looks at his new watch. In a deleted scene at his farewell party, Toby refers to an undefined incident involving his sister; this marks the first time Toby has mentioned having any siblings, although late in season 7 he reveals also having a brother Rory.[8]

In season five, Toby is revealed to be in traction in a Costa Rican hospital, with a broken neck, after a zip-line accident on his third day in Costa Rica. He explains that he has yet to see the beach, but expresses some happiness with the camera crew for visiting. He also implies in an earlier talk with Oscar that he is attracted to a woman who is visiting a nearby resort with her husband, thus continuing his tendency to fall for unavailable women à la Pam. In a deleted scene from Baby Shower, Toby can be heard on the speakerphone with Holly, noting that he enjoys his stay at the hospital more than his treatment from Michael at the office.

In "Frame Toby", it is revealed that Toby had returned to the office for a week without Michael noticing. When the staff tells Michael that Toby is back, Michael thinks it's a joke until he sees Toby and screams "No God! Please No! No!" Michael asks David Wallace to get rid of Toby but the CFO says he can not fire Toby without cause. Michael then attempts to get Toby fired by giving Pam a fake letter to give to Toby, asking him to hug and kiss her no matter how much she resisted, and taunting the HR rep into punching him, but both plans fail. Michael then tries out Dwight's idea of planting drugs in Toby's desk (unknowingly buying basil from a caprese salad from warehouse workers who he thinks sold him marijuana). However, he does feel guilty about what he has done and, when the police are investigating the "drugs", Michael tells the police that it's a mistake and tries to stop them from arresting Toby. This suggests that, while Michael does hate Toby, there are limits to his hatred. Then again, Toby's reaction to the setup—that it wasted the cops' time that could have been used to deal with law enforcement—inspires more shock and disgust from Michael.

He is seen on occasion in the background in the "Annex" of the office. When Michael gives his two weeks notice, Toby shows he is not as resentful towards Michael as Michael is to him in a talking head, referring to him as a movie on an airplane, which is nothing special but something to watch. He was seen breaking up a jam session in the lunch room up between Dwight and Andy who were attempting to impress the new receptionist with guitar and banjo to the song "Take Me Home, Country Roads" by John Denver. Toby simply says, "You have to stop."

In "Stress Relief", Toby is seen attempting to help the others escape Dwight's fire drill. In the second part of the episode, during the roasting of Michael, Toby begins to walk to the mike but Michael stops him declaring that only friends are allowed to roast him and Toby agrees and sits back down and laughs with the rest of the audience at Michael being roasted. It is possible Michael stopped Toby from roasting him not only because they are not friends but because Toby would have the worst things to say about him.

He is also involved in the episode "Casual Friday" where he has a talking head about his beginnings at Dunder Mifflin. He used to be in seminary, but he left because he wanted to have sex with a girl named Kathy and took the HR job at Dunder Mifflin so he could be with her. Kathy is revealed to be the name of his ex-wife, and he does not appear to have a passion for HR. In the same episode, he has to deal with complaints about a too relaxed dress code by Oscar and Meredith. For the first time, he is stern with his employees and enforces HR policy by cancelling Casual Fridays at the office.[9]

In the episode "Gossip", Michael spreads rumors about various people throughout the Office, including that Toby is a virgin, even though he has a daughter.

In the episode "The Meeting", Dwight and Toby investigate a dishonest workman's compensation claim filed by Darryl, an event which results in Dwight and Darryl filing complaints against each other, leaving Toby to "drown in a sea of paperwork." During the episode, Toby ends up bonding with Dwight when they share an interest in trains, and finds that Dwight is restoring a life size one in his slaughterhouse.

Although he does not appear, directly, in the episode The Promotion, Michael and Jim put baked beans on pictures of the employees as a way to decide the raises. Jim then sees a drawn picture of what looks to be a clown with a caption saying "I'm an idiot" and asks Michael who it is, Michael answers, saying it is Toby. Jim reminds Michael that Toby is not part of this and Michael answers "I just wanted to draw a picture of him".

In the episode "Niagara", Toby kindly offers Michael the second bed he has in his room but Michael insults him by telling him he will be sleeping alone for the rest of his life and walks away. Toby seems to at least have some feelings left for Pam, as he seems to be happy when reacting to a possibility of Jim and Pam's wedding being called off. When the wedding does go on, however, he is seen dancing with the others and cheering Jim and Pam on as they walk down the aisle at the ceremony's end.

In the following episode, "Mafia", Oscar comments that with Jim and Pam off on their honeymoon and Toby having "mentally checked out in June" he is the only person left to counter insane antics with rational thinking. When hearing of Oscar's comments Toby casually agrees with him.[10]

In the episode "The Lover", Toby is yelled at by both Michael and Jim when he walks in on them just after Michael has told Jim he is dating Pam's mom. Later, after Pam blew up at Michael in the conference during an office meeting, Michael comes to Toby desperate to make Pam happy about his relationship with her mother. Toby offers to talk to Pam for Michael and Michael even goes as far as hugging Toby and calls him a good good-guy. Toby is extremely happy at the hope that things will finally change between them that he says "you know I always knew that if Michael just took the time to get to know me, we would be friends." But once Toby is unable to smooth things over, Michael dismisses Toby as a jackass and goes right back to hating him.

In the episode "Koi Pond", Toby is present in the meeting where Michael wants to talk about insults in the office and as usual when Toby simply makes a point Michael insults him by calling him a waste of life, though corrects himself claiming that's what he would like to say but the meeting is an insult free zone. However, when Michael reveals he has fallen into two fountains Toby appears to find this funny and laughs at Michael. After this, he asks for Michael to kick him out of the meeting and Michael tells him to go.

In the episode "Double Date", Toby talks to Pam to make sure she plans on hitting Michael off grounds. He then gives Pam some tips on how to punch harder, even going through motions with her on how to do it as Michael watches on from his office, visibly afraid.

In the episode "Secret Santa", Toby is called "Antichrist" for calling Michael's Jesus costume inappropriate. In "The Banker" Toby is interviewed by an investment banker as he evaluates the branch. Michael tries to have Toby distracted while Dwight impersonates him but Toby appears and makes Dwight leave. Despite knowing of several questionable incidents that have taken place in the office, he does not say anything to the banker. He expresses his torn feelings about this in a talking head.

In "Whistleblower", Toby is revealed to have written a few chapters of a mystery novel and receives advice on the plot from Jo Bennett to which he replies in an interview, "Write your own damn novel!"

In "Nepotism", as a punishment for physically injuring an employee, Michael is sent to a 6-hour counselling with Toby. In a deleted scene, Toby tells the camera crew that he finished writing his book over the summer and got four sales out of his self-publishing but is being sued for plagiarism.

In "Counseling", Toby does counselling for Michael. They briefly become friends as Michael talks to Toby about his life, but when Michael realizes that Toby is, in fact, counselling him, Michael yells at him. Toby reveals that he has a degree in social work. At the end of the episode, however, he seems to be communicating with Toby civilly, as most of his anger is fixed on Gabe Lewis.

In "Costume Contest", Toby dresses up as a hobo. In a deleted scene, while using a Ouija board at the office Hallowe'en party, he mumbles that "being dead is going to be so relaxing", disturbing his co-workers.

In "Christening", Toby has trouble entering the church where Jim and Pam's baby is being christened. After many false starts, he finally enters the chapel and can be seen in front of the altar asking "Why do you have to be so mean to me?"

In a deleted scene from "WUPHF.com", he is talking with his daughter via web chat, where he finds out through her that his ex-wife has a new boyfriend. Michael shuts off Toby's laptop and then proceeds to talk with him about the situation he is in with Ryan. Toby tries to offer the best advice he can, but as usual, Michael brushes off what he says and then pokes fun at the fact that someone else is banging his wife.

In "Classy Christmas" Toby has to go on leave so he can report for jury duty. The case turns out to be that of the Scranton Strangler, a fact Toby lets slip out despite his not supposed to be talking about the case. He later says to the camera crew he likes the attention. Michael is visibly disgusted when Toby returns on jury recess to attend the Christmas party and tells the staff to not ask Toby any questions as he will not leave and this will prevent Holly from returning. In the second part of the episode, Michael attempts to frame Toby for vandalizing Holly's beloved Woody Doll but Toby immediately denies it and flips it around on Michael claiming the vandalism is something he would do, to which everyone agrees to eventually.

Toby has a minor role in Michael Scott's film "Threat Level Midnight" as a hostage. When the villain Goldenface (played by Jim), decides to show the hero (played by Michael Scott) how serious he is, he decides to kill a hostage, naturally picking Toby. When Goldface shoots Toby's character, his head explodes in an overly dramatic fashion. However, Michael tells Goldenface that the joke is on him, saying that Toby was a "wanted animal rapist".

Toby returns in "Michael's Last Dundies", where he appears to have lost a considerable amount of weight. In the beginning of the episode, Michael eggs his house in the morning and drives away. Toby is later seen at the Dundies sitting with Jim and Pam. Michael awards Toby with the "Extreme Repulsiveness" award (with Deangelo commenting how mean that is). Toby refuses to accept it but is told he has to by the other employees because Michael is leaving. Toby then reluctantly accepts it, but tells Michael he finds the award hateful. He then goes on to say that he is taking advantage of being up on the platform, and lets everyone know that the jury found The Scranton Strangler guilty and that he is being put to death. However, Toby is now having doubts about the verdict, saying he thinks the Strangler might be innocent, but is interrupted by an "Oh Yeah" sound effect from Dwight's synthesizer.

In "Goodbye, Michael", Michael is seen saying goodbye to Toby without insulting him, possibly indicating that he will miss Toby on some level. However, Michael is visibly disgusted when he learns that Toby has a brother, Rory (played by Paul Lieberstein's real-life brother Warren), who lives in Boulder, Colorado as well. Later, Toby is seen talking to Rory via Skype and tells him he thinks his brother and Michael would "hit it off in an odd way". Rory suggests that he could bring Michael a welcome basket, and asks Toby if Michael likes Jams, but Toby informs him that Michael hates them.

In the beginning of "The Inner Circle", Deangelo informs Toby that he is getting a new chair, but Deangelo, trying to be confusing so the staff will not "figure him out", tells Toby he does not care if he likes it. Toby is still grateful.

In "Dwight K. Schrute, (Acting) Manager", he gets to fill out the gun violence accident form, much to his excitement. After Jo demotes Dwight upon learning of his gun accident, she appoints Toby as one of the search committee members who would be in charge of interviewing candidates for the manager position (along with Jim and Gabe).

In "The List", new CEO Robert California makes a list of the people in the office, dividing them between perceived "winners" and "losers"; he takes the winners out to lunch. Although Toby is on the list of "winners", he concludes that it must be a mistake, and excuses himself in the middle of lunch.

In "Lotto", Toby says in a talking-head interview that if he won the lottery, he would not change his life at all, except for quitting his job, moving away, and maybe re-entering the dating world.[11] He also says he would spend a lot of time launching his true-crime podcast, "The Flenderson Files".

In "Garden Party", Toby arrives at "Schrute Farms" and asks Dwight's cousin, Mose, where to park. Mose states that he is the valet and that Toby has to give him his car. Reluctantly, and after much pressure, Toby lets Mose park his car. It proves to be a bad choice, however, as Mose drives his car straight into a cornfield (though it is not damaged, and becomes the first of many cars parked there in odd, Mose-chosen order).

In "Spooked", Dwight and Robert California's son Bert hearken back to the days when Toby was continuously mistreated by Michael when they "prank" Toby by telling him he is fired. Toby finds Bert's treatment of him hurtful—especially Bert saying he can have Toby fired because he is the CEO's kid—and Dwight finds the whole bit hilarious.

In "Test the Store", Toby has a rare substantial role in a Season 8 episode, where he leads a self-defense lecture for the employees after they believe Andy was attacked by a gang and left with a black eye (Toby and everyone else later find out Andy was punched by a rude 4th-grade girl when he defended Pam from a barrage of tossed pine cones). When Toby is not aggressive enough for Kelly Kapoor's taste, she stands up and begins threatening and swinging at him, after which Andy defends Toby and gets punched in his other eye.

In "New Guys", Andy returns from Outward Bound manager training, making him become more "decisive and confident". When Andy tells Toby that he plans to fabricate an excuse to fire Nellie, Toby shoots down the idea as a violation of corporate policy, prompting Andy to tell Toby "I understand why Michael didn't like you." When Andy hosts a motivational exercise involving a tightrope, he insults Toby and Nellie in front of the staff. Since that time, Andy has been rude towards Toby in a manner that echoes Michael Scott's hatred of his harmless HR rep, though Toby seems much less affected by Andy's behavior than he was by Michael's. When Andy went off on his long boat trip, Toby's time in the last season was devoted to his unrequited romantic interest in Nellie Bertram and his belief that he'd convicted an innocent man during his jury time on the Scranton Strangler case (a theory he put to rest when he went to visit the convict in prison and was, in fact, choked and nearly strangled by him). In the series finale, it's revealed that Toby was fired immediately after Dwight fired Kevin Malone (it's likely that the Corporate office fired Toby and Dwight simply had the burden of telling him) and Toby then moved to New York where he is trying to become a novelist and has six roommates. Toby surprises his former co-workers at the reunion panel when he says that his life feels meaningless now that he is not being filmed for the documentary anymore. He breaks down in tears while dancing with Pam at Dwight and Angela's wedding, saying of what's bad in his life that "It's everything!", but he seems cheered a little when the group insists he join them for post-wedding festivities. In a photo gallery NBC released of "where are they now?" info-bits for the characters, it's revealed that Toby has returned to his destiny by taking on an HR position at a TJ Maxx store.