Michael tends to overestimate his importance to his employees, but despite constantly offending some of them, he has a close bond with them. Most of the employees have been the focus of Michael's jokes at one point or another, usually in reference to their race, sex, size, attractiveness, or sexual orientation. Examples of Michael's difficult relationship with his staff include getting slapped by Kelly for being racist, hitting Meredith with his car, getting kicked out of Phyllis and Bob's wedding, and
outing Oscar to the entire office without his permission. They are, however, generally sympathetic to his shortcomings and, while regularly losing patience when he interrupts their workflow, often try to assist him with his personal problems. Michael's relationship with the company warehouse employees is tense. He has a tendency to disrupt their daily work flow, and in a talking head interview, warehouse supervisor
Darryl Philbin (
Craig Robinson) explains that they have never been able to make a full year accident-free because of Michael's antics.
CFO David Wallace tolerates Michael's antics because he values his loyalty to the company, but Michael offends
CEO Alan Brand and the rest of the executives during his only meeting with them. Although many Dunder Mifflin employees are initially barely able to tolerate Michael, they gradually grow to appreciate his sincere intentions, even at times coming to find amusement in his sophomoric humor and behavior; this transition is most apparent in
Pam Halpert, with whom he eventually develops a genuine friendship. His co-workers are overjoyed when Michael finds his soulmate in
Holly Flax; they participate in his romantic proposal to her and are shown to be emotional at his leaving Scranton to be with her. Jim Halpert even teared up while calling Michael "the best boss [he] ever had."
Dwight Schrute Dwight has the most respect for Michael, viewing him as a model for success, and is thrilled when asked to handle any task given to him, however ill-conceived it may be. Although on the surface, Michael usually appears dismissive of Dwight and generally views him as a suck-up, he is genuinely hurt and angry at the few times when Dwight has deceived him, such as when Dwight went over Michael's head to vie for the manager's job or when refused to reveal office secrets to Michael's new company, the "Michael Scott Paper Company". In the episode "
Heavy Competition" of Season 5, Dwight takes Michael's
Rolodex and finds his own business card, on the back of which, Michael had written (before leaving Dunder Mifflin): "Dwight Schrute, tall, beets". Michael also cares how Dwight feels about him. After Michael beats Dwight at his own dojo, Michael finds out that Dwight no longer wanted Michael as his primary contact in case of an emergency which causes Michael to promote him from "Assistant to the Regional Manager" to "Assistant Regional Manager", with a three-month probational period. Dwight told Michael in Season 6 that Michael's pathetic career path hurt Dwight and he regretted working for him instead of taking a fast-track job at
Home Depot, but they buried their differences later on. When Deangelo Vickers arrives to be the new Branch Manager, Dwight is depressed that he didn't get the job after Michael recommended him, only to learn from Gabe that Michael didn't recommend him after all. At first Dwight is angry with Michael, but they make amends when Michael gives him a letter of recommendation on his final day at
Dunder Mifflin. They end the day with a paintball fight behind the building. In the
series finale, Michael is the best man at Dwight's wedding after Jim arranges it.
Ryan Howard Michael has one-sided affection for
Ryan, which often makes Ryan uncomfortable. Examples of this are when Michael gives Ryan the "Hottest in the Office" award in
The Dundies, when Michael declares he would definitely want to have sex with Ryan in "
The Fire", and when Michael gives Ryan a $400
iPod for the Secret Santa gift exchange, despite the 20-dollar limit. In "
The Deposition", a page from Michael's diary reveals he describes Ryan as "just as hot as Jan, but in a different way." On multiple occasions, Michael behaves inappropriately around Ryan, including slapping Ryan's buttocks, pinching Ryan's nipples, staring constantly at Ryan from behind his window blind, pinning Ryan to sit on his lap and making kissing gestures toward Ryan while calling him
the belle of the ball. Michael is devastated when he finds out about Ryan's arrest for fraud, and much to the dismay of David Wallace, he later re-hires Ryan. In "
Prince Family Paper", Michael acknowledges that his heart has led him astray before, naming Jan and Ryan as examples of this. In "
Dream Team", Michael convinces Ryan to leave his job at the bowling alley and join his newly formed paper company. When working together, Ryan comes to respect Michael's skills as a salesman. In Season 7, Michael heavily invests in Ryan's WUPHF.com and won't agree to sell his majority shares when it is clear Ryan is exploiting Michael's goodwill and is incapable of saving the venture from bankruptcy. Michael's obsession with Ryan is further shown in a number of deleted scenes. In one from "
Diwali", Carol says that Michael constantly talks about Ryan's attractiveness and has begun stalking Ryan. In another from "
Safety Training", Michael confesses that he will miss Ryan the most after dying, which angers Ryan. In a deleted scene of "
Beach Games", Michael says he especially wants to see Ryan put a hot dog in his mouth. In "
Night Out", Michael is in bed with Ryan asking "Do you miss us?," to which Ryan declines to answer.
Jim and Pam Halpert Michael doesn't hesitate to compliment or criticize Pam for her looks and he frequently mentions her breasts. In the episode "
Diwali" Michael mistakenly thinks that he and Pam have a connection, and is rejected when he tries to kiss her. Throughout their relationship, Pam has served as something of a
shoulder angel for Michael by encouraging him to be more productive and discouraging his bad ideas, with varying degrees of success. She grows closer to Michael as he supports her goals in pursuing sales and art. Pam is visibly touched when, after many art show attendees (including Oscar and his boyfriend Gil) dismiss her artwork, Michael is so impressed that he asks to buy her painting of their office building. Their relationship comes to a rocky point when he begins dating her mother Helene. This is only repaired after he breaks up with Helene and allows Pam to slap him in the face in the parking lot. He trusts and respects Jim, although when they were co-managers they clashed due to their polar-opposite management styles. In "
Secret Santa", Michael mentions that in a future vision he sees himself and his future wife living next door to Jim and Pam and that their children will play together. He often also refers to Jim as his best friend in the office, although, based on his impersonation of Jim using surfer slang in "
Michael's Last Dundies", does not have a very good understanding of his personality. While Jim and Pam are both shown to care about Michael, his clingy nature makes them reluctant to socialize with him outside of the office; such as when, after numerous unsuccessful invitations, Michael is forced to trick them in order to have them over for a disastrous dinner in the episode "
Dinner Party." In a Season 5 episode, Michael also shows his admiration for Jim, when Jim wears a tuxedo to work and goes on and on about having a 'classy party' for the party planning committee, and frequently suggests all of the ideas Dwight had offered that Michael had then rejected, only to bother Dwight by having Michael accept the same ideas from him. During Cecilia Halpert's baptism, Michael approaches Pam referring to himself as "the godfather" while imitating
Don Corleone. After Pam sympathetically but emphatically asks him to acknowledge that he won't be Cece's godfather, he is disappointed but does so, and is hurt to learn that the godparents are a couple they'd only recently met. Pam is shown to have a soft spot for Michael, such as when she consoles him after he finds Holly to be in a relationship with AJ, and when she advises him on how to propose to Holly. In "
Goodbye, Michael" it is revealed that Michael is secretly planning to leave for Colorado at the end of his penultimate work day, thereby avoiding having to say goodbye to everyone. Jim figures this out and goes along with it, telling Michael that he will tell him what a great boss he was the following day at lunch, which they both know Michael will not be around for; Michael and Jim both get sentimental during this final conversation between them. The strength of his relationship with Pam is revealed as he continuously asks about her whereabouts, not wanting to leave without saying goodbye. Pam, who spent the better part of the day away from the office, finds Michael at the airport and says goodbye in a touching scene just as he's about to board his plane for Colorado. She watches from the window as his plane flies off. In a deleted scene of "
The Inner Circle", Pam is flattered that Michael named his new dog "Pamela Beagsley." Pam later teases Jim that their second child will be named "little Michael Scott" displaying the friendship she had developed with her former boss. In the
series finale, Jim convinces Michael to replace him as the "bestest mensch" at Dwight's wedding. Pam is so thrilled to see photos of Michael's children that she does not judge him for paying for two phones to hold all the pictures.
Toby Flenderson Despite liking the majority of the staff, Michael fiercely hates
Human Resources Manager Toby Flenderson. The origins of Michael's hatred for Toby go largely unexplained in the show itself, although writer/executive producer
Paul Lieberstein, who also portrays Flenderson, has said that the genesis of the joke for the writers was in a deleted scene where Toby signs Meredith's birthday card. Within the context of actual aired scenes, Human Resources Manager Toby often has to reprimand Michael for violating company policies, which is consistently a source of friction between the two. Michael's long-time goal is to get rid of Toby and any attempts at reconciliation between the two usually backfire. In the episode "
Goodbye, Toby", Michael is thrilled when Toby decides to move to
Costa Rica and gives as his going away present a rock with a note that reads "Suck on this". The next season, after Toby's replacement Holly is transferred, Michael is horrified when Toby returns to Dunder Mifflin. In "
Frame Toby", he goes to great lengths to get him fired, trying to frame him for possession of
marijuana, and although he later admits his actions to the cops out of guilt when they initially prepare to arrest Toby (indicating his hatred has limits), he ends up hating Toby, even more, when the latter criticizes him for wasting the cops time instead for being framed (it is possible that Michael is disgusted that Toby lets himself be abused). In "
The Chump", Michael says if he had a gun with two bullets and was in a room with
Adolf Hitler,
Osama bin Laden, and Toby, he would shoot Toby twice. In "
Nepotism", after Michael spanks Luke, the office intern who is also his nephew, he is ordered to attend counseling sessions moderated by Toby, much to Michael's horror. At first Michael is uncooperative but is gradually tricked by Toby into discussing therapeutic details of his life and childhood. In "
Michael's Last Dundies", Michael eggs Toby's house while he and Deangelo are handing out Dundie nominations in the cold open. In "
Goodbye, Michael", Michael is seen saying goodbye to Toby without insulting him, possibly indicating that he will miss Toby on some level in spite of his tremendous animosity towards him.
Erin Hannon Once Pam is promoted to salesperson following Dunder Mifflin's buyout of The Michael Scott Paper Company, Michael keeps
Erin Hannon as her replacement. Michael is initially unkind to her as he misses having Pam as his receptionist, but she is able to earn his respect by cheering him up after his disastrous school visit in "
Scott's Tots." Unlike her predecessor, Erin loves working as a receptionist, admires Michael and cheerfully accommodates many of his unusual requests (such as serving him a plate of
ants on a log every day at 2:30 and spinning him in his chair until he's dizzy). Although he generally enjoys Erin's thoughtful treatment, his dismissive feelings towards Erin continue until "
Secretary's Day" when he reluctantly agrees to take her out to lunch. Erin relishes the opportunity to spend time with her boss, while Michael finds their conversation awkward and mentions that her then-boyfriend
Andy Bernard was previously engaged to
Angela Martin. Erin was previously unaware of this, and after learning of it she ends her relationship with Andy. Later that day, Michael apologizes to Erin; the two are finally able to relate to each other over their mutual fondness for silly humor, stemming from their similar immature tendencies with Michael's ignorance and Erin's naïveté. Their working relationship then develops smoothly while they bond by making each other laugh with childish jokes, such as Erin pointing out that the phrase "it's not" sounds like "snot." In "
Viewing Party", Erin throws a
Glee party with her new boyfriend,
Gabe Lewis. Throughout the night, she unsuccessfully attempts to get Michael and Gabe to bond. Michael is jealous that the office looks to Gabe as the boss and attempts to sabotage the party. After being confronted by Erin in private, Michael questions why his opinion matters so much to her as he is not her father. In a moment of insight, Michael realizes that Erin, who was raised in foster care, does indeed look to him as a father figure and he instigates a playful fight as father and daughter by saying "go to your room, young lady!" Erin becomes protective of Michael to the point where she is hostile towards Holly Flax, saying in a talking head interview that she doesn't understand what Michael sees in her, until
The Search when she, Dwight and Holly go searching for a missing Michael. Erin sees that Holly is able to sense where Michael is, and when she sees them reconcile, she finally understands their love for each other and smiles. Later in "
Goodbye, Michael", Erin talks to Michael about her love life and wishes that she knew her birth mother so she could tell Erin what to do. Michael advises Erin that she shouldn't rush things and that she'll know what to do when the right guy comes along. Michael then tells her that she won't need her mother for advice, because she will always have his personal phone number when she needs advice and kisses her on the head.
Holly Flax Shortly after the dissolution of his troubled relationship with Jan, Michael found love with
Holly Flax (
Amy Ryan), Toby's replacement as HR Representative, who appears for a while to be Michael's best chance at love, with the two sharing a similar sense of humor and social awkwardness. However, after David Wallace witnesses them kissing, Holly is transferred to the
Nashua branch and she and Michael break up after choosing not to pursue a long-distance relationship. Despite the breakup and Holly's new relationship with another man, their affection for each other persists, as it is shown that Holly had been writing a note for Michael on her work computer, as well as their subtle romantic glances at one another during the summer company picnic. Throughout her absence in Season 5, excluding "Company Picnic" and carrying on into Season 7, Michael hooks up with a few other women, but ultimately he finds that none of them compare to Holly. Around Christmas in Season 7, Toby is forced to leave the office due to being selected as part of the jury duty for a local murder case, resulting in Holly returning as the temporary HR replacement. There is initial tension between the two of them and hesitation on her side (mostly after her sudden break-up with A.J.), but Holly finally reunites with Michael after realizing the two are soulmates. The two continue dating for a few weeks, and on Valentine's Day, they tell each other they love each other, decide to move in together, and resolve that they will not allow Dunder Mifflin to interfere with their future together. With her time at the Scranton branch almost up and the recent knowledge that her aging parents need to be taken care of, they ultimately become engaged. Holly later moves back to Colorado and Michael follows her soon after. In the finale it is revealed that they have children together. It was revealed in a photo album on NBC that they have three children and are expecting their fourth child.
Other romantic relationships Michael's longest relationship before his marriage was with
Jan Levinson (
Melora Hardin), his original-then-former boss from Corporate. Starting with a one-night stand after they closed their business deal at
Chili's in "
The Client", Michael and Jan begin awkwardly dating, become an official couple, and eventually move in together after Jan is fired from her job—although Jan usually treated Michael with contempt. After Michael fails to defend Jan in her
wrongful dismissal suit against Dunder Mifflin, they remain together for a short while, but end up blowing up at each other during an ill-fated dinner party and eventually break up. He also dated Carol (played by Carell's wife
Nancy Walls), a real estate agent from whom Michael bought his condominium. Michael was much more interested in Carol than she was in him, and after he made an unwanted and rejected impromptu public marriage proposal, Michael's decision to
Photoshop pictures of himself over Carol's ex-husband in her family pictures resulted in their breakup. On a business trip to
Winnipeg, Michael and "Concierge Marie" become close, and Michael does not wish to leave her after they are caught necking in her suite. After Jim and Pam's wedding, Michael begins dating Pam's mother Helene (much to Pam's horror), but he breaks up with her on her birthday after discovering she is turning 58. Near the end of season six, Michael begins dating Donna (
Amy Pietz), the manager of a local bar, but later finds out that she's married and he is, as he puts it, "the mistress". He continues seeing her until the disgust of his employees drives him to listen to his conscience and break things off with her. In Season 7's "
Sex Ed", Michael reunites in person or by telephone with all of his past girlfriends when he believes that he has contracted
herpes. In doing so, he realizes that Holly was the only one he truly loved. ==Legacy of "That's What She Said"==