The Office: The 10 Most Important Milestones In Michael & Holly’s Relationship

Jim and Pam might be talked about the most when it comes to romantic pairings on The Office, but Michael and Holly end up playing almost as important of a role in the plot. It’s this relationship that allows Michael to have a believable and well-loved ending in the series, even if he was gone before the show wrapped completely. This relationship was the only one Micahle had that isn’t toxic or wrong for him, and while things didn’t get off to an easy start for them, they eventually worked it out.

Michael and Holly’s relationship had some interesting stops and starts along the way, and these key moments made for a rather fascinating, and often hilarious, love story.

10 Holly Replaces Toby As HR Rep

This is the milestone that starts it all. While Michael was already thrilled that Toby was going to take his trip to Costa Rica, he was even happier once he realized that Holly wasn’t going to be as boring as Toby. It didn’t take Michael very long to warm up to Holly, and they were joking with each other right away.

Unfortunately, things hit a bit of a road bump when Jan’s pregnancy was discovered by Kevin. And, in true Michael fashion, he really messed things up at first by thinking he should get back with Jan.

9 The Disastrous Ethics Seminar

While Michael and Holly seemed like they’d make a good match early on in their relationship, there was one sequence that threw a wrench in this. When Holly was in charge of the ethics seminar, Michael, unsurprisingly, didn’t take it seriously.

Holly was unimpressed by how he ignored Meredith’s questionable behavior, and Michael was annoyed at Holly for actually caring. It was one area where these two weren’t completely compatible and also a conflict of interest as Holly’s job was to enforce the rules of the company.

8 They Started Dating

Holly and Michael’s relationship started rather quickly before being pushed to an abrupt halt, but, while they were briefly dating, things went well. They had good rapport as Holly also enjoyed pop culture references and was a bit of a dork in the same way Michael was. Plus, they seemed to have physical chemistry in a healthier way than Micahel had experienced with Jan.

However, while they did get along well, their dating experience was rather short. They didn’t get to know each other beyond this surface-level before David Wallace learned of their relationship.

7 Holly Is Sent To Nashua

On the one hand, it’s easy to be frustrated with David Wallace sending Holly away from Scranton. It seemed like it wasn’t his place to break up a couple, especially when dating wasn’t against company policy. However, given Michael’s disastrous relationship with Jan and its impact on Dunder Mifflin, the impulse makes sense.

Holly leaving for Nashua was rather devastating to Micahel especially, but it was also a bit surprising when Holly didn’t even try at all to make things work long-distance.

6 Michael Steals The Letter Off Holly’s Computer

When Michael and Pam go on their tour of the branches, they go off-schedule by heading to Nashua. Since Holly isn’t there, Michael gets onto her work computer and downloads a letter Holly had written to him. While this did feel a bit like a plot contrivance, it provided a message to fans that this relationship might not be over.

Pam ended up reading the letter and telling Michael that Holly did still have feelings for him. Not much happened after this for a while, but it did illustrate that Holly wasn’t gone for good.

5 The Company Picnic Skit

This moment was a bit of a mixed bag for their relationship. On the one hand, they got to bond over their shared humor, work together one-on-one, and Michael was somewhat chill about the fact they weren’t dating and able to enjoy the friendship. On the other hand, they also revealed to the Buffalo branch that they were all about to be fired.

However, despite this awkward moment, neither of them seemed all that phased. Michael is overall a rather selfish character, so it makes sense that he would only care that he had a good day with Holly.

4 Holly Comes Back To Scranton

While Holly had been gone for all of season 6, she was reintroduced into the show in season 7. This reunion prompts Michael to go all out and act rashly to throw the Classy Christmas party. And, this is the beginning of a real relationship between these two.

However, while Michael assumes they will just fall into each other’s arms, Holly is still dating AJ. This comes as quite a shock to Michael, and he shows his immaturity once again by trying to ruin the Toy Story doll that AJ gave Holly.

3 Holly’s Ultimatum/Michael’s Expectations

While things seem like a dead-end between Michael and Holly, it’s revealed that Holly and AJ’s relationship isn’t going that well. Holly tells the women of the office that she’s going to give him an ultimatum, and Michael gets the idea that after the holidays, Holly will be single.

However, it doesn’t all go that smoothly. Holly doesn’t actually give the ultimatum, and she’s still with AJ. Michael doesn’t take this well, but fans were able to see that Michael and Holly were likely going to get back together eventually.

2 They Start Dating Again

The episode when Holly and Michael get back together is meant to show just how perfect they are for each other. After Michael gets lost at the gas station, Holly is the one who is able to track him down just by doing what she herself would do.

While it’s a rather sweet idea that ends with these two kissing and starting up their relationship, it did stretch their connection a bit too far. Relasticially, they didn’t know each other all that well, and they also hadn’t always gotten along perfectly either.

1 Their Sweet Engagement

Michael and Holly’s engagement was a surprisingly sweet moment that was also a big fire hazard, even if Pam did reign Micahel in somewhat. However, it ended with the sprinklers going off and became a rather magical moment.

While this led to Michael leaving for Colorado to be with Holly, it was probably the best ending the character could have had. He got a happy ending while also getting character growth as Dunder Mifflin was no longer the most important thing in his life.

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