Fictional Characters Wiki

"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's a school night, and you know, uh... Hooters is catering. You know, is that not—is that enough? Should I keep going?"

  • Toby, after shutting down Michael's plan to invite Boy Scouts to Casino NightToby Wyatt Flenderson M.S.W. (born 1971) is a character in the NBC sitcom The Office. He is played by showrunner Paul Lieberstein.

Toby is the Human Resources representative at Dunder Mifflin Scranton. Toby can be somewhat mournful about his life choices (he fell into the field of Human Resources after leaving his training at a seminar to pursue the woman he would marry, and eventually divorce). He likes to colleagues, but is sometimes annoyed by the excessively chatty Kelly Kapoor. He had a long-standing crush on former receptionist Pam Beesly, which he almost reveals to her at the end of season four before he moves to Costa Rica.

Former branch manager Michael Scott greatly despised Toby, largely due to Michael not having any authority over Toby since he reported to corporate headquarters, and because Toby disapproved to Michael's 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? 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, 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 that he has a degree in social work from Temple University. Toby was in a seminary for a year but dropped out because he wanted to have sex with a girl. He followed her back to Scranton, married her and had a young daughter named Sasha, who adores Michael. Toby is alsodivorced (a fact which Michael constantly and unkindly mentions). Toby loves his daughter and went the extra mile in "Moroccan Christmas" to buy her one of Dwight's Princess Unicorn dolls, noting that his ex-wife "will be so pissed" and that "for once, Daddy's going to be a hero." He went to Amsterdam for a week (or a month) after his divorce.

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 Scottpublicly reads off all listed complaints.

Toby is in the unfortunate position of needing to try (but usually failing) to enforce corporate policies and rules when Michael disregards them, which most notably shown when Michael tries to invite children to the office's casino night.

Toby 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. However, he gets along with the rest of the staff and even attends Jim's barbecue party, playing video games while Michael sings karaoke. When Dwight approached Michael about missing a gift bag during "A Benihana Christmas," Michael immediately 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). In addition, whenever someone says they are having problems at the Scranton branch, Michael immediately asks if the problem is Toby's fault, and the answer has always been "no." In many cases, that person will continue on, saying that Toby was in fact kind and helpful.

He seems to have plain bad luck in many instances in his life. It seems to be a recurring theme that some sort of tragedy befalls him frequently, if only in a minor sense. He sadly accepts his misfortunes, seeming 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).

He once 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. Also, according to a deleted scene from the episode "Launch Party," it is stated while Toby is taking a driver's test that 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 (which he called the "silent killer," leading to Michael saying "You are the silent killer. Go back to the annex."); and he put together a meeting to discuss the radon testing kits he was dispersing in "The Chump."

Seasons 1 - 2[]

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.

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 "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 by far 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."

Seasons 3 - 4[]

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 everyone believes she is a paid escort. Toby says, "We met at the gym, why is that so hard for everyone to believe?" 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.

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's "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's 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.

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 Toby sees Pam kiss Jim he sends out a memo about Public Display 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 can't 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 4:58PM on a Friday so no one would attend. Jim agrees, but comments that he likes Toby but that the guy is really annoying him. 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.

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 toCosta 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. 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's kind of cute. Toby faces a cruel exit interview from Michael but the tables are turned when the new HR rep, Holly, and Pam join the interview. Michael is unable to berate Toby at length, but does threaten to kill him if he honestly answers the question "How can Dunder Mifflin be improved?," so Toby gives a "things are OK as they are" answer. Toby gets revenge when Michael's insulting farewell gift to him is exposed and Pam gets Michael to give up his watch to Toby. 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. In a deleted scene at his farewell party,

Seasons 5 - 6[]

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 "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 acaprese 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 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 canceling Casual Fridays at the office.

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.

In the episode "Niagara", 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, he is not seen dancing with the others or 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.

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's 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 "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!"

Seasons 7 - 8[]

In "Nepotism", as a punishment for physically injuring an employee, Michael is sent to a 6-hour counseling 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 counseling for Michael. They briefly become friends as Michael talks to Toby about his life, but when Michael realizes that Toby is in fact counseling 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 "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.

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's 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.

n the beginning of "The Inner Circle", Deangelo Vickers informs Toby that he is getting a new chair, but Deangelo, trying to be confusing so the staff won't "figure him out", tells Toby he doesn't 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 wouldn't change his life at all, except for quitting his job, moving away, and maybe re-entering the dating world.[10] 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 isn't 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's fired. Toby finds Bert's treatment of him hurtful—especially Bert saying he can have Toby fired because he's 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 pinecones). When Toby isn't 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.

Season 9[]

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 tight-rope, 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, strangled and nearly killed by him). In the series finale, it's revealed that Dwight fired Toby immediately after he fired Kevin Malone (why Dwight now had authority to fire an HR representative is unclear, as the show had always made it explicitly clear that Toby reported to the Corporate office in New York rather than to a local Branch Manager) and Toby then moved to New York where he's 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's 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.


Toby is seen as an awkward and quiet guy in the office. Nobody ever stands up for Toby when Michael makes fun of him, but he is generally liked in the office. 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. He is considered one of the few intelligent people in the office, being in the "Finer Things Club" with Pam and Oscar.

Michael Scott[]

Michael hated 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.

Michael viewed Toby as his sworn enemy and took 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" (Immediately following the above quote from Toby regarding the Casino Night). At various times, Michael has referred to Toby as "the worst human being ever," a "convicted rapist," "evil snail," "animal rapist," "Satan" and "theAntichrist." Michael once says that if he "had a gun with two bullets and was in a room with Hitler, Bin Laden and Toby, [he] would shoot Toby twice."

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. Some 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.

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.

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. 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. While they both attend Dwight and Angela's wedding, they are not shown to interact in any manner (for example, Toby breaks down in tears over his terrible life at the reception, but Michael does not react with happiness over Toby's misfortune).

Pam Beesly[]

Toby has had a crush on Pam ever since she called off her wedding with Roy and Jim went to Stamford, but he is too shy to tell her his feelings. In "Cocktails" Toby spends his whole evening trying to win a stuffed animal duck at a claw machine for her. When he finally wins, Pam gives back the stuffed animal and says "Don't you have a daughter?". In "Dunder Mifflin Infinity" Toby is the first to find out about Jim and Pam's relationship, by seeing her kiss him on the cheek in the break room. Upset about Pam's new relationship, he sends out a memo asking for no "PDA" in the office. In the episode "Business School," Pam asks Toby to come to her art show, and he says he can't make it because of his daughter's play. He then gets really upset and yells, "Damn It!" and questions if maybe he doesn't have to go to see his daughter's play and instead could go see Pam's art show.

In "Night Out," Pam thinks that a joke that Toby told was funny, and he gets really excited and touches her awkwardly on the leg. After an awkward silence, Toby announces his move to Costa Rica. In "Goodbye, Toby" Pam gives to Toby an office picture of the staff that excludes her (because she took the picture herself) for when he leaves for Costa Rica. Toby, unsatisfied by the lack of her presence, shouts at the office staff asking for a camera (possibly the loudest he's ever spoken). When no one responds, he runs off for an extended amount of time just to find a camera to have a picture of her and him together. At the end of the episode, Pam comments (though not to Toby) that she always thought he was kind of cute. In "Niagara" Toby appears to still have feelings for Pam, and is happy when they run out on their wedding. He is later disappointed when the wedding is called back on, but is seen smiling and clapping after they're married and run down the aisle. During "Roy's Wedding", while Jim and Pam are trying to find out if there's anything they don't know about each other, Toby correctly answers facts about Pam. Everyone notices him, and Toby, clearly embarrassed, attempts to cover it up. In the series finale, while dancing with Pam, Toby began sobbing. Pam questions Toby with "Is it me?" Toby shakes his head, and responds with "It's everything."

Jim Halpert[]

Jim mentions that when he first started working at Dunder Mifflin, he shared a cubicle with Toby and that the two of them got along well. Michael moved them apart because he thought that the two talked too much. In deleted scenes from The Fire and Take Your Daughter to Work Day it's implied that Toby and Jim are friends and Jim babysits Toby's daughter on occasion. When Jim becomes Co-Regional Manager with Michael in season six, however, Jim almost begins to mirror Michael's treatment of Toby. In "The Lover", when Toby casually says "Hi", a stressed Jim snaps "Not now Toby! My God!" leaving Toby bewildered and hurt. In the earlier "Survivor Man", Jim also says about Toby "He's great, but sometimes he can be a little bit much." Jim was aware of Toby's crush on Pam but never seemed very bothered by it. However Toby would occasionally be bitter towards Jim, as seen in "Did I Stutter?" where he assists Ryan (now Vice President) in giving Jim a formal warning for his job performance. During "Stairmageddon", Jim turns to Toby for advice on marriage counseling over coffee, given Toby's past experiences before divorcing his wife.

Kelly Kapoor & Ryan Howard[]

Toby shares the Annex with Kelly, and he is exasperated at being in the close proximity of Kelly and Ryan's juvenile romantic escapades. Using the excuse that he was allergic to his desk, Toby moved locations to escape Kelly's constant talking, moving out of the cubicle, albeit only to a desk adjacent to it. Toby later wonders if Michael intentionally moved Ryan to his former area in order to torture him via Ryan and Kelly's endless fighting, commenting that "If he did... genius." Kelly stated in a deleted scene from Goodbye, Toby that she was attracted to Toby but could not stand "his stupid kid" and was visibly downcast when he announced his plans to leave the office and move to Costa Rica.

Darryl Philbin[]

In a deleted scene from "Ben Franklin," when warehouse foreman Darryl Philbin is told that Michael has sent Toby home to prevent him from interfering with the hiring of a stripper, Darryl refers to Toby ("that red-haired guy with the sad eyes") as a cool guy. While on a trip to the Corporate offices with Darryl and Michael in "The Negotiation," Darryl also offers to let Toby crash for the night at a relative's house in New York, denying Michael the same opportunity. He also had a nickname for Toby ("T-dog") at one point, though their relationship soured when Dwight's plan to expose Darryl's workers compensation fraud led to embarrassment for all of them.

Andy Bernard[]

Toby and Andy did not appear to have any major disputes when Andy was a salesman or during his first year as manager. In "New Guys", when Toby shoots down Andy's intention to make up a cause to fire Nellie Bertram, Andy responds "now I know why Michael hated you so much". Toby appeared dismayed at this. Andy later ridiculed both Toby and Nellie during the slack-lining later in the episode. Andy continued his irritability in "Work Bus" when asking Toby "how are you not murdered every hour", suggesting he, like Michael and Jim before him, has inherited the typical manager's disdain for Toby.

Toby appeared aware of Andy's poor treatment of Erin as a girlfriend, which he pointed out to Nellie in "Customer Loyalty". In the finale, however, after Andy returns with a more positive and friendly attitude, Toby is pleased to hear him (and several other staff members) encourage him to join them at the after party in the warehouse, implying the two are now on good terms.

Nellie Bertram[]

In "Get the Girl", Toby introduces himself to Nellie as Tony, to which Pam replies "You messed up saying your name?" He answers her by saying, "It happens, okay?"

In "Dwight Christmas", at the office Christmas party, Nellie expressed interest upon hearing that Toby had been a juror in the Scranton Strangler case. He proceeds to bore her, however, with a long, drawn-out account that is implied to have lasted for several hours. Nellie finally leans in close and shushes him. A puzzled Toby then asks if she is about to kiss him. Attempting to save face, Nellie gives him a small kiss, which causes an emboldened Toby to give her a much more passionate kiss.

Toby does not appear in the two subsequent episodes, during which the events of the party are not referenced. In "Customer Loyalty", however he appears very tactile and affectionate towards Nellie, apparently under the impression that the two are now in a relationship. Nellie, for her part, had forgotten the kiss until that point, and finds Toby's affection somewhat awkward.

In "Moving On", Nellie gets fed up with Toby's constant hand-wringing over the possible non-guilt of the convicted Scranton Strangler and pushes him to visit the man in prison; when the Strangler proves he is the killer and nearly kills Toby himself, Nellie admits Toby was brave and a speechless Toby (his larynx was injured by the Strangler) looks happy. However, Nellie later firmly establishes her contempt for Toby and there is no further romantic storyline between them.

When Toby returns to Scranton for the reunion and Angela & Dwight's wedding, Nellie (also returning to Scranton from her new home in Poland) lets the camera crew know she isn't thrilled about seeing Toby again. At the airport, Nellie rebuffs an attempted hug from Toby, snidely brushes aside his comment about a relationship she ended by saying she un-followed him on Facebook (Toby quietly says anyone can read non-protected tweets) and declines his offer to share a cab into town. After that point, Toby has no further interactions of any kind with Nellie.

Pete Miller & Clark Green[]

After the departure of Kelly and Ryan, Toby appears more excited with the arrival of the two twenty-somethings who are single like himself. He appears to see them as closer friends than they see him but neither of them treat him meanly either. He convinced both of them, along with Kevin and Darryl, to grow mustaches from "Movember", believing this was a bonding activity. He was disappointed when Pete shaved his mustache off, after Erin found it off-putting.

Toby appears to consider Pete a better fit for Erin than Andy, largely because he doesn't appreciate Andy's belitting treatment of him and also because he never had any romantic interest in Erin. At the documentary reunion, Pete is nice to Toby and is visibly happy when Toby decides to attend an after-party he had been planning to skip.