Michael and Holly’s relationship timeline on The Office was complex because of where they were tly employed and the circumstances around dating someone in the workplace. There were multiple in-office relationships at Dunder Mifflin Scranton, but for whatever reason, the CEO, David Wallace, found it to be a problem for the regional manager to date the temporary human resources transfer. This bump in the road was a huge turning point in not just Michael’s relationship with Holly but his working relationship with David.
Aside from becoming best friends with his employees, Michael’s dream was to be a husband and father. He thought he found love with his former boss, Jan Levinson, but that relationship turned out to be toxic, and he thought he found love again with Donna, but she turned out to be married. Every woman Michael dated before Holly didn't mean a thing to him once he met the right person. Here's the timeline of Michael and Holly's relationship on The Office.
Season 4, Episodes 18-19: Michael & Holly Met At Toby's Going Away Party
In The Office season 4, episodes 18-19, "Goodbye, Toby," Holly was transferred to Dunder Mifflin's Scranton branch to cover for Toby, who was quitting his job for a new life in Costa Rica. Before meeting Holly, Michael told Dwight how much he hated her because HR and managers never got along. To his surprise, Holly understood his humor, was loving, and was a great listener. Michael changed his tune with Holly, and the attraction between them was mutual. Their introduction was a significant milestone in Michael and Holly's relationship because it's what started their love story and gave Michael what he's always wanted: a suitable romantic partner.
Season 5, Episode 3: Michael & Holly Became Best Friends In The Office
By the time of The Office season 5, episode 3, "Business Ethics," Michael and Holly had become even closer. In the episode, Michael – who usually loved leading a meeting – had Holly co-lead a presentation on business ethics with him. Their choreographed dance and reworked cover of the song "Physical" ("let's get ethical") made it clear that these two had a stronger connection than Michael ever had with another person. Holly even called him her best friend in the episode. At this point, Holly became a regular Office character who was changing Michael for the better, but there were a few things holding their potential relationship back.
Season 5, Episode 4: Michael & Holly Go On Their First Date After Jan's Baby Shower
Although Michael wanted to act on his feelings for Holly, he held himself back because his ex-girlfriend Jan was having a baby. Michael had no relation to that baby whatsoever but was so infatuated with the idea of being a dad that he thought he could be a part of the baby's life in some way. This changed in The Office season 5, episode 4, "Baby Shower." The Scranton branch held a baby shower for Jan, not realizing that Jan had already had the baby. Michael's views on being a father figure to her child changed after this.
There were plenty of theories on who the father of Jan's baby was, but what mattered was where Michael stood with the situation. Realizing a shifty life with Jan and her baby was not what he wanted — and after being cold to Holly all day because Jan was around — Michael asked Holly on a date. This was a huge step for Michael because it proved he was ready to move on and find happiness with someone who felt as ionate about him as he did for her.
Season 5, Episode 5: Michael & Holly Break Up When Holly Gets Transferred To Nashua
Holly and Michael's relationship was cut short when their mistake led to an office break-in. After dating for a few days, Michael and Holly had sex in the office and forgot to lock the door on their way out. It was one of Michael and Holly's more awkward moments, as thieves broke into Dunder Mifflin and stole valuable company property. What followed was a fundraiser in The Office season 5, episode 5, "Crime Aid." With CEO David Wallace being there to the branch, he saw Michael and Holly kiss, which raised some red flags. David didn't want a repeat of Michael and Jan, so he felt it was best to transfer Holly.
Transferring Holly meant another loss for Michael. Although they planned on dating long-distance, they broke up when Michael was moving Holly into her new house because the distance to Scranton was too far. Losing Holly was important for Michael's character because it was a time to reflect on what he actually wanted in life and whether working at Dunder Mifflin was worth it.
Season 5, Episodes 16-17: Michael Found Out Holly Had A New Boyfriend
Michael proved to be a good boss despite his chaotic ways. A great example of this was when he went on a road trip with Pam to perform lectures at different Dunder Mifflin locations about being a successful branch. In The Office season 5, episodes 16 and 17, "Lecture Circuit," Michael and Pam went to the Nashua branch for a lecture — and to see Holly. It was there that Michael found out Holly was dating a salesman at the office. This was one of the lowest points in Michael's arc because he felt replaceable. While peeking at her computer, however, he found a letter to him from Holly, proving she still loved him.
Season 5, Episode 28: Michael & Holly Reunite At The Company Picnic
Dunder Mifflin employees attended their annual corporate retreat in season 5, episode 28, "Company Picnic." Michael knew he'd see Holly there but also knew she'd be there with her boyfriend. In one of the more embarrassing things at the Office company picnic, Holly and Michael performed an awkward skit for the branches as entertainment, but it went horribly wrong. Doing the skit together still led to sweet conversations about their acting abilities and their friendship. Instead of being upset over Holly having a boyfriend after a great day together, Michael knew he couldn't rush the future of their relationship and was oddly calm about where they stood by the end.
Season 7, Episodes 11-12: Holly Is Transferred Back To The Scranton Branch
In The Office season 7, episodes 11 and 12, "Classy Christmas," Michael found out that Holly was being transferred back to Scranton while Toby had jury duty for a couple of weeks. With Holly being back in town, Michael assumed they would get back together. To his dismay, she was still with her boyfriend. While Michael and Holly had a good relationship, he acted childish when he realized her boyfriend was worth staying with, but he wasn't. This could have been a great time for growth for Michael, but instead, he spent the next couple of episodes questioning why they weren't together, which only bothered Holly because she felt pressured.
Season 7, Episode 15: Holly Realized She Wasn't Over Michael
Not long after moving to Scranton, Holly realized her relationship with her boyfriend wasn't going anywhere, and in The Office season 7, episode 13, "Ultimatum," she broke up with him. Holly wanted some time to figure out what she wanted, but that came short in season 7, episode 15, "The Search" when Michael got lost in Scranton. Without a phone to call on, Holly thought, "What would Michael do?" and eventually found him when no one else could. This showed they had one of the most compatible relationships in The Office and they shared their first kiss since breaking up years prior. This was a huge moment in their storyline.
Season 7, Episode 16: Michael & Holly Start Dating Again
In The Office season 7, episode 16, "PDA," Michael and Holly were better than ever. They were fully back together and even declared they loved each other. The branch knew Michael never stopped loving Holly but to hear that Holly felt the same was an endearing moment for their relationship timeline. Michael and Holly realized in this episode that she would eventually be transferred back to Nashua, but this time, they promised to make their relationship work.
Season 7, Episode 19: Michael Proposed To Holly And The Two Left Scranton For Good
Michael and Holly had never been better than in The Office season 7, but when Holly found out that her dad's health was declining, she wanted to move back home to Colorado — bringing Michael with her. Knowing that Michael and Holly were soulmates, it made sense for the couple to continue their relationship outside of Scranton. Michael then took the opportunity to solidify their relationship and proposed to Holly at the office with the help of his employees. For the first time, Michael was finally getting his happy ending with a woman who deserved him, but this meant the end of an era for Dunder Mifflin Scranton.
Season 9, Episode 25: Michael & Holly Went On To Have Four Kids
The finale of The Office showed Dwight and Angela's wedding, but it didn’t feel right without Michael since he and Holly moved to Colorado at the end of season 7. In a shocking twist, Michael showed up as Dwight's Best Man and all was right in The Office fandom. It wasn't said why The Office didn't include Michael and Holly's wedding, but in a sweet conversation with Pam, it was revealed the couple went on to have four kids and were happier than ever.
Michael and Holly's union on The Office was a long time coming, and it gave Michael a complete ending. After more than 15 years at Dunder Mifflin, there was nothing left for him to accomplish with the company. Moving on to a new career and life outside of Scranton was what he needed in order to grow and achieve his true dream: a loving family.