Michael-Ryan Relationship

"I’m not blind! I know exactly who he is. He is selfish and lazy and image-obsessed, and he is a bad friend. And he’s also clever. And he shoots incredibly high. And he may just make it. But you know what? Even if he doesn’t, I would rather go broke betting on my people, than get rich all by myself, on some island like a castaway. And there is no middle ground."

Overview
Michael has a very one-sided fondness for Ryan that often makes Ryan very uncomfortable. Despite the better treatment he received from, for example, Dwight, Michael often favors Ryan over everyone else in the office, given him special treatment. He makes various suggestive gestures to Ryan, like when he gives him the "Hottest in the Office" award in "The Dundies," confesses that he would definitely want to have sex with Ryan in "The Fire," and in his personal diary, Michael says that Ryan is "just as hot as Jan, but in a different way" in "The Deposition." Along with that, he often makes sexual remarks to Ryan, once saying that in prison he would be da belle of da ball, before proceeding to make kissing noises at him.

Michael also shows a genuine investment in Ryan's life, devastated when he discovers that he was arrest in "Goodbye, Toby." And in "Dream Team," convinces him to join the Michael Scott Paper Company after he tracks him down to working in bowling alley, also getting him a sales job upon his company's merging with Dunder Mifflin.

Ryan often takes advantage of this friendship Michael believes they share, getting him to invest in WUPHF.com, despite his poor management forcing them to sell the website domain name when it becomes apparent that the website will go bankrupt.

Season 1-3
For the first episode and for much of season 1, Ryan's purpose in the show mirrors that of his British equivalent, Ricky Howard. He is the audience surrogate, allowing other characters to introduce themselves to him, and by extension, the viewer. He is present in the pilot episode, when Michael, as a really mean joke, pretends to fire Pam, clearly made uncomfortable when breaks down crying in front of them, Michael then revealing his lie, saying it was his and Ryan's idea.

In "The Fire," Ryan accidentally starts a fire at the office trying to cook a cheese pita. Upon Dwight discovering this fact and telling Michael, the two make fun of him by singing a song they create called, "Ryan Started the Fire."

In "Performance Review," it is revealed that Ryan was hired to replace Tom Peets, an employee who lost a battle with depression and committed suicide shortly before the start of the documentary.

In "The Injury," Michael burns his foot on his George Foreman Grill, and frequently makes Ryan run errands, often that either him or Pam do favors for him, instead of Dwight, who is more than willing to help. When Michael falls off the toilet in one of the bathroom stalls, he asks that Ryan lift him up and clean him up, who refuses, terrified at the prospect, with Toby coming with a half-hearted excuse, saying "Ryan is...dead."

By the third season opener "Gay Witch Hunt", Ryan becomes a full-time employee and inherits the job vacated by Jim Halpert. Despite the promotion, Michael still treats Ryan as his personal assistant.

In "Business School," Ryan brings Michael to his college as a guest speaker, because if he brings his boss to class, it will automatically bump him up a full letter grade. Michael doesn't hear Ryan's introduction, wherein Ryan explains how Dunder Mifflin is a dying company. Michael accompanies his entrance with a Brandenburg concerto playing from a boombox and begins his speech by ripping the pages out of a student's expensive textbook. Michael illustrates his description of how to start a business with a series of candy bars, throwing them to the incredulous audience.

Ryan redirects the speech into a question-and-answer session. Michael solemnly states that "real business is done on paper," and tells the students to write that fact down. The Q&A session intensifies, with students wondering aloud how a small business could survive against the "five Goliaths" of the paper industry. Michael defends his company, commenting at the students' inability to understand the situation based upon their age and lack of experience. He also states that the United States faces "five goliaths" as well but only states four: Al-Qaeda, Global Warming, sex predators, and mercury poisoning. When a student uses Ryan's prediction of Dunder Mifflin's obsolescence as proof of his point, Michael is shocked to hear that Ryan had made such a statement. He informs the room that Ryan still hasn't made a sale, started a fire in his attempt to make a cheese pita, and "a lot of people think he's a tease." He heads for the exit, shouting, "Ryan doesn't know anything, and neither do any of you. So suck on that!"

In the car ride back, Michael tells Ryan to clean out his desk. Ryan has mixed feelings when he learns that he is simply being relocated to the annex... right next to Kelly. Michael then comments to Ryan that "... a good manager doesn't fire people, he hires people and inspires people... people will never go out of business". The words of wisdom surprise Ryan.

In "The Job," Michael is interviewed and rejected a position at corporate, only for Ryan to get the job, despite his inexperience.

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.

Season 4
In "Dunder Mifflin Infinity," Ryan unveils the idea for a new website for the company. Michael protests this idea, due to his dislike of technology, trying to prove that the company doesn't need it by sending their ex-clients gift baskets with Dwight, only for it to go horribly wrong, coming back to inform his employees that Dunder Mifflin will not be investing in any new technology, which Ryan explains isn't the case.

The episode "Night Out" begins with Ryan arriving at the Scranton branch and noticeably friendlier than on his previous visits. Ryan shows the staff at the branch the new Dunder Mifflin website, "Dunder Mifflin Infinity 2.0", the previous version of which was shut down because sexual predators had invaded the social networking component of the site. As Ryan leaves, he tells Michael of the women he meets in clubs in New York City. Michael and Dwight subsequently decide to go to New York, locate Ryan, attend parties with him, and try to meet women while doing so.

In New York, Michael and Dwight locate Ryan after discovering which club Ryan frequents; the latter appears to be under the influence of drugs (coke) but Michael and Dwight do not notice. Later, Michael, Dwight, Ryan, and Ryan's colleague, Troy Underbridge wait outside another club, but fail to get in because they do not have dates. Dwight comes to the rescue when he manages to pair each of them with members of a women's basketball team, who are also waiting in line. Inside the club, Ryan's dancing becomes erratic and aggressive, and he accidentally hits a girl, prompting her friends to attack Ryan. Dwight and Michael escort him out of the club, and after Troy advises them not to take Ryan to a hospital, he runs off. Michael and Dwight bring Ryan back to his apartment, where he tells them that he thinks "his friend Troy" has a drug problem, and asks what he should do about it. Michael, oblivious to the fact that Ryan is obviously referring to his own drug addiction, gives him hypothetical advice involving a wiretap and snitching on a drug dealer.

Michael is then very worried when in "Goodbye, Toby," Ryan is fired and arrested for business fraud, misleading the company shareholders about the website sales.

Season 5-7
In "Weight Loss," Ryan is released from prison on a sentence of community service, and has gone sober. Michael hires Ryan through the temp agency as the fill-in receptionist. In a deleted scene, he receives a call from David Wallace for Michael. Infuriated that Ryan is back at Dunder Mifflin, Wallace abuses Ryan by telephone in front of the staff. This prompts Michael to defend Ryan and save his job. However, Ryan still exhibits the ego issues he developed in the fourth season. Ryan is also creeped out when Michael copies his goatee.

In "Dream Team," after Ryan had left the company to go to Thailand (later revealed to be Fort Lauderdale), Michael tracks him down to a bowling alley, and hires him to work at the Michael Scott Paper Company.

After the buyout of The Michael Scott Paper Company by Dunder-Mifflin in "Broke," much to David Wallace's vocal opposition, Ryan is initially rehired as a salesperson, though, as a result of budgetary problems, is reduced back to the position of a temporary employee in "Casual Friday" by Michael, who instead decides to keep Pam as a salesperson.

In "The Sting", he helps Jim, Michael and Dwight spy on Danny. When they try to hatch a plan, Jim tells Ryan he is a "hot new executive" and Ryan tells them he wants to work at Google.

In "WUPHF.com", Ryan gets people at the office to invest in his new social media site. When he reveals he will be broke in nine days, everyone is worried, before Ryan tells them that he has an offer from the Washington University Public Health Fund (WUPHF), only for Darryl to realize that they are only interested because of the domain name. Ryan tries to weasel more money from Michael but is caught by surprise when Michael tells all the other investors that while he will not agree to divest their WUPHF holdings (they need Michael's assent because he holds more than 50% of the shares). He does reveal that he thinks Ryan is shallow and a bad friend and Ryan looks horrified when Michael says he has those nine days to make things right. At the end of the episode, Ryan tells everybody he has sold WUPHF.com, much to Michael's relief.

In "Garage Sale," Ryan is in the group that helps Michael think of a good way to propose to Holly. When Michael does propose to Holly, he has some employees jokingly ask Holly to marry them. He states that Ryan was the only one he was concerned about.

In "Michael's Last Dundies", he is shown to be upset that Danny Cordray broke his streak of winning the "Hottest in the Office" award, although he tries to hide it. Ryan's contribution to the office workers' version of "Seasons of Love" is that Michael helped him get off drugs. And in "Goodbye, Michael", Michael gives Ryan his St. Pauli Girl beer sign, but only after making sure he is not prone to seizures. Ryan seems to genuinely appreciate the gift.