Michael-Holly Relationship

"Holly and I are like Romeo and Juliet. And this office is like the dragon that kept them apart." Michael and Holly are one of the main couples of The Office. They get engaged in the seventh season. They have been married for 11 years (2022). They move to Colorado together. It is revealed that they have 3 children and are expecting a fourth child.

Season 4
Holly arrives at Dunder Mifflin Scranton in "Goodbye, Toby" to take over the HR job of Toby Flenderson, who is moving to Costa Rica. At first, Michael seems very unpleasant to Holly, since he thinks Holly follows the stereotype of Toby, who is arch-enemies with Michael. Michael even goes as far as asking Dwight to haze Holly, which Dwight does, claiming to Holly that Kevin has special needs.

However, Michael starts to see that Holly is different from Toby, and is momentarily at a loss for words when Holly says that Toby bored her to death when he was showing her the HR files. Michael goes to Jim for help, and he suggests that Michael take it slow and first make friends with Holly.

Michael spots Holly on the floor of The Annex, fiddling with Toby's old chair. She says that she's trying to adjust the lumbar support and strikes up a conversation with Michael. They seem to be very similar, being right at home with one another and having fun changing their voices and joking around.

At Toby's going-away party, Michael and Holly sit on the Ferris wheel together and are having a grand time. Unfortunately, their happy moods fizzle and disappear when Dwight, still on his hazing mission, shoves a raccoon into Holly's car with the help of his cousin Mose Schrute. When confronted, Dwight says that Michael told him to do it, which isn't exactly untrue. Holly seems shocked, but Michael praises Holly, saying that she's the "Best thing that ever happened to this branch!" Holly seems touched and Michael recovers nicely.

Later, after Michael belts out a parody of "Goodbye Stranger", Holly is impressed and asks him out for dessert. But Michael doesn't seem to understand that she's asking him out on a date, and declines, leaving her to take Kevin instead.

Season 5
In "Weight Loss", Holly asks out a yoga instructor, since she's under the impression that Michael is not interested in a romantic relationship. But Michael is, and he is a bit jealous. Holly and Michael's bond grows stronger, and Holly's relationship with the yoga guy is going downhill. In fact, he never calls back to confirm their concert date, and Holly now has extra tickets. She sells them to Michael, who rips them apart instead of just going to the concert with her.

In "Business Ethics", Michael and Holly disagree for the first time. When Meredith Palmer admits that she has done something unethical, Holly wheedles Michael to fire her, but Michael is protective of his subordinates and does not budge. Their friendship is still intact, though.

Disaster strikes when Jan Levinson, Michael's ex-girlfriend, gives birth to a baby from a sperm donor. Michael tells Holly to not be alarmed if he's cold to her, since it is a front for Jan's sake. Holly is shunned all day and seems a bit miserable. However, Michael is unsuccessful in hiding his friendship with Holly, and Jan asks him to not date her. This compels Michael to ask Holly out, and she happily accepts. ("Baby Shower")

Michael and Holly have their first date in "Crime Aid". They plan to have sex and leave the office late. Michael and Holly have their first kiss in the stairwell of the office building before leaving, forgetting to lock the door in their high spirits. Because of this, the office building is burglarized, and computers are stolen. Holly and Michael decide to have an auction loosely based on Farm Aid. They kiss at the end of the auction in the warehouse, oblivious that Dunder Mifflin CFO David Wallace spots them. Trying to avoid another office romance involving Michael, David Wallace sends Holly back to Dunder Mifflin Nashua.

Holly goes to Nashua with Michael in Darryl Philbin's warehouse truck in "Employee Transfer". They have a grand time singing in the truck and chatting animatedly, but Holly realizes that it will be difficult to date long-distance. After she is dropped off in Nashua, her and Michael decide to end things.

In "Lecture Circuit", Michael and Pam go on a tour of many of the Dunder Mifflin  branches to spread the secret of Scranton's success. After they depart Dunder Mifflin Utica and Pam gets closure from Karen Filipelli, Michael wants the same and they decide to go to Nashua to get closure with Holly. Once there, he realizes Holly is on an HR training and is in a relationship with a salesman named A.J. Michael finds an unfinished file on Holly's computer that says "Letter to Michael." Michael copies the file to a flash drive and Pam later reads it for him. Pam says that Holly still has feelings for Michael, then deletes it. It is unclear if she is being honest or is just refraining from further hurting Michael's feelings.

In the final episode of Season 5, "Company Picnic", Holly and A.J. come to the picnic together. Holly and Michael have to put on a skit about the history of Dunder Mifflin. Michael is able to stay cool and collected, but is seen looking disappointed when Holly and A.J. walk off to their car and leave the picnic.

Season 6
In "Whistleblower", Sabre CEO Jo Bennett and Michael have a talk, and Jo says that he could ask her for any favor. Michael requests for her to bring Holly back from Nashua, and Jo says that she'll see what she can do.

Season 7
Michael is afraid he has herpes in "Sex Ed". He calls all of his ex-girlfriends to warn them, and when he gets to Holly, she says that she doesn't love him anymore before they hang up.

In "Classy Christmas" Toby has to leave to be on jury duty for the Scranton Strangler trial. Jo keeps her word and sends Holly to be his replacement. To Michael's dismay, she is still living with A.J., but he isn't making a move to propose, even after nearly two years of being together. Holly is cornered by Kelly and Phyllis, and they pressure her to give A.J. an ultimatum for marriage.

In "Ultimatum", everybody is anxiously waiting to see if Holly has a ring on her finger when she comes to work for the first time since the deadline. Holly realizes that everybody knows about the ultimatum and shows everybody her ring fingers, which are bare. At first, Michael is overjoyed, but he finds out that Holly and A.J. have not broken up yet. Holly is pressured once again, and once again, she cracks, and tells A.J. over the phone that they should take some time away from each other.

In the next episode, "The Seminar", Michael vies for Holly's affections, but she doesn't respond. Andy Bernard is putting on a seminar for small business owners, and he isn't doing very well. Holly and Michael come to his rescue and put on a skit, just like old times.

In "The Search", Jim abandons Michael at a gas station because of an emergency with his daughter, Cece. In his haste, he accidentally leaves Michael's phone in his car and Michael comes out of the gas station bathroom with no way to contact anyone. Dwight, Holly, and Erin all form a search party and scour the city around the gas station.

Michael ventures to a hot dog stand, a noodle house, and a pet store, among other places. In an uncanny way, Holly goes to each of the places in the search for Michael, showing the similarities between the two. Eventually, Holly finds Michael at the top of a building. Realizing their connection, the two passionately kiss.

In "PDA", Michael and Holly make their relationship public. Too public. They seem to know no boundaries between private and public manners and are shown kissing, fondling each other's body parts, and overall just flirting in front of the other office workers. Everyone finds it disgusting and band together to ban Michael and Holly's PDA. Later that day, Michael comes to the crushing realization that Holly will have to go back to Nashua when Toby returns and he's depressed. Holly retorts by saying that they can decide their future, not a company.

In "Garage Sale", Holly talks with her parents in Colorado over the phone. They appear to have dementia, and Holly seems genuinely worried about them. She meets Michael in the break room and tries to propose to him so they can live together in Colorado, but Michael sprints away, explaining to the cameras that he doesn't want his "Proposal Story" to be held in a break room.

Michael starts to think of elaborate and irrational proposal plans, starting with a scheme where he slathers gasoline over the parking lot in bold letters. Before he can light up the gasoline proposal message, but Pam talks him out of it, along with other concerned workers. Together, all of them decide on an elaborate proposal.

Michael acts it out perfectly. He starts with showing Holly around to important places for their relationship, and opens the door between the annex and the regular workspace. All the office workers hold candles and ask Holly to marry them. She declines each, and Michael leads her into the annex, where all of the desks and drawers are covered with candles. Unfortunately, this triggers the annex fire sprinklers, but Michael proposes anyway and Holly accepts.

It is confirmed that Michael and Holly have three children with a fourth on the way.

Status: Married