Until the fourth season of got rejected in front of hundreds of people. He was unhappy in an on-and-off relationship with Jan for years. But in the season 4 finale, he met his “soup snake,” Holly Flax, and it was love at first sight.
As Holly was transferred away and fell in love with someone else before she ended up with Michael, their relationship was far from smooth sailing. Here are the 10 most pivotal moments in Michael and Holly’s relationship.
When They First Met
Michael decides he doesn’t like Holly before even meeting her. He hates his branch’s HR rep Toby more than anything in the world, so he assumes he’d hate Toby’s replacement, who takes over for him while he was in Costa Rica.
However, when Michael actually meets Holly and gets talking to her, he instantly falls in love. He decides to make her a mixtape for the commute to and from work, and calls Jim into his office to tell him that he was in love.
When Jan Told Michael Not To Date Holly
When Jan comes to the office for her baby shower, Michael is unaware that she’d already had the baby because she was supposed to call him when she went into labor.
Jan asks Michael not to date Holly, which only reaffirms Michael’s feelings and leads him to finally ask her out.
When They First Slept Together In The Office (And Accidentally Let In Some Robbers)
On their third date, Michael and Holly sleep together in the office. When they come into work the next morning, they find that the place has been ransacked.
Each of them thought that the other one would lock the front door behind them, so they left it unlocked, allowing the break-in to happen. Out of guilt, they organize an auction to recoup some of their losses.
When They Decided Not To Try A Long-Distance Relationship
When David Wallace finds out that Michael and Holly are dating, he decides to remove any chance of a conflict of interest by transferring Holly to another branch.
Michael takes a personal day to help her move up to Nashua, but along the way, they realize that a long-distance relationship won’t work and they end their relationship, at least temporarily. On the drive back to Scranton with Darryl, Michael is heartbroken, and they sing the blues to cheer him up.
When Michael Stole Holly’s Sleeve
In the two-parter “Lecture Circuit,” in which Michael and Pam go around the company’s branches to deliver lectures about how to be more successful, Michael initially intends to avoid Nashua. However, he has a change of heart after seeing Pam reconnect with Jim’s ex Karen and decides to go. But he finds that Holly isn’t even there and she has a new boyfriend, A.J., so he breaks down in the middle of the lecture.
Later, Michael goes to Holly’s desk, cuts off one of her sleeves, and steals a file from her computer called “Dear Michael.” Pam reads it and confirms that Holly still has feelings for him.
When They Did A Skit About The History Of Dunder Mifflin At The Company Picnic
When David Wallace recruits Michael and Holly to do a comedy skit about the history of Dunder Mifflin at a company picnic, Michael intends to tell Holly that he’s in love with her and he believes they’re “soup snakes” (meaning “soulmates”).
In the end, Michael decides not to tell Holly how he feels and instead just waits for their relationship to flesh itself out. He explains, “I think we are one of those couples with a long story when people ask how we found each other.”
When Michael Trashed Holly’s Woody Doll
When Holly gets transferred back to Scranton from Nashua, Michael is excited to rekindle their relationship. However, he finds that after breaking up with Michael when she was transferred to Nashua, Holly stays with A.J. when she's transferred back to Scranton.
Consumed with jealous rage, Michael throws the Woody doll that A.J. bought for Holly in the trash and pours coffee on it.
When Holly Found Michael On A Roof
After an emergency at home forces Jim to leave Michael stranded in a gas station bathroom, he wanders around Scranton.
Dwight’s leads get nowhere in the search, but Holly has a kind of magical connection to Michael that makes all of her hunches turn out to be correct. At the end of the episode, she finds him on a roof and they kiss.
When Michael Proposed To Holly
Michael’s proposal to Holly is one of the most heartwarming moments in the entire series. He sets up candles around her desk and gets down on one knee. Although it sets off the sprinklers, it was still a wonderfully romantic gesture.
When Michael Moved To Colorado To Start A Life With Holly
There’s a bittersweet quality to the episode “Goodbye, Michael.” On the one hand, it’s heartbreaking to see Michael bid his co-workers farewell.
But on the other hand, there’s a hopeful element in Michael finally having someone to share his life with.