The Office was one of the greatest workplace comedies of all-time. So much so, that we all find ourselves still quoting it nearly daily. With Michael Scott at the helm of the Scranton branch of Dunder Mifflin Paper Company, we watched him grow and evolve while still being his blissfully idiotic self.
During Michael's seven seasons on the show, we watched the many ups and downs in his relationships. Whether he was in his on again/off again relationship with his boss, Jan Levinson, or dating Pam's mom, Helene, or falling in love with Holly Flax, the new HR rep, he was always having misadventures in his dating life.
But when he met Holly Flax at the end of season 4, it really did seem like everything changed for him. He was able to fully be himself around her and his feelings for her never wavered, even when they were apart. Throughout their relationship and the breakups and makeups they endured, there were several milestones and new developments that always kept fans on the edges of their seats. In Holly Flax, Michael Scott met his perfect match.
For all of you The Office fans, here are the 25 Wild Revelations About Michael And Holly's Relationship.
25 Michael Didn’t Say “That’s What She Said” Around Holly
We all know Michael Scott’s favorite joke was “That’s what she said.” But as soon as he met Holly, he reined in his incessant need to make those jokes, which was a huge deal for Michael. This was first shown when Holly made an off-hand remark while on a ferris wheel outside the office with him.
His reaction was to make his crude joke, but stopped himself and carried on the conversation normally. This meant that Holly was a game-changer for Michael.
24 He Let Go Of His Hate Of HR Reps When He Met Holly
One of the things we could always rely on when watching The Office was Michael’s deep hatred of HR reps and more specifically, Toby Flenderson. He considers HR to be the people who suck all the fun out of working in the office and are just there to get you into trouble.
But when he meets Holly - Toby’s replacement - he goes from being wary of her to being completely enchanted by her presence. This was a major departure from Michael’s past feelings towards HR.
23 Michael Fell In Love With Holly Nearly Immediately
On Holly Flax’s first day, Michael felt that he fell in love at first sight with her. Or when he heard her voice, would be more accurate. In Michael’s own words, it was “Well, it’s love at first sight. Actually it was…No, it was when I heard her voice. It was love at first see with my ears.”
Michael may have been known for falling hard and fast with the people he dates, but this was a new record even for him. And little did we know that his feelings for her then would lead to a beautiful relationship.
22 Michael Was Mean To Holly To Protect Jan
Jan Levinson was Michael’s former boss and ex-girlfriend by season 5. She also fell pregnant and no, it wasn’t Michael’s. But Michael still wanted to be involved and even threw her a baby shower at the office.
So what did he do when it came to Holly? Pretended he hated her and was outright mean to her whenever Jan was around. This was apparently to protect Jan’s feelings. But in the end, Michael ended the charade and asked Holly out instead — against Jan's wishes.
21 Jim Advised Michael On Their Friendship Before They Began Dating
Jim Halpert is the classic romantic. After many ups and downs in his own love life with Pam, the office receptionist, they were finally together by the time Michael met Holly. And since they were happy and in love, Jim felt the need to help Michael with his budding romance with Holly. But with baby steps.
On the first day Michael met Holly, he was in love. So Jim helpfully told him to start with friendship and “court” her around the office while they get to know each other. It would naturally progress from there. And he was, of course, right in his assessment.
20 Their Romance Nearly Ended Before It Started Because Of Meredith
During the infamous ethics seminar that Holly had in the office and Michael assisted with, Meredith admitted some pretty damning things she had done that weren’t ethical at work. Holly felt compelled to report her troublesome activity, while Michael didn’t want Meredith to get in trouble, or worse, fired.
They had a major disagreement over this issue and it nearly cost them their friendship, and in turn, any potential romance between them from happening. Luckily they made up, but it could have been a lot worse.
19 They Are Both Dorks
Michael is known around the office for his pranks, inappropriate jokes, impressions, pop culture references, and even magic tricks. In other words, he’s a complete dork. And he found his dorky counterpart in Holly Flax.
It was obvious early on she was just as dorky, if not more so, than Michael. Which is a very big reason they got along so well. It’s also why their relationship worked far more than any other woman Michael had dated in the past. They not only accepted each other's dorkiness, but reveled in it.
18 Holly Gave Up On Their Relationship When She Was Transferred
Once their boss, David Wallace, caught wind of their relationship, he immediately transferred Holly from Scranton to the Nashua branch. Michael and Holly’s plan was to try a long-distance relationship — try being the operative word.
But after only one drive to Nashua from Scranton, Holly realized it would be extremely hard on both of them with how far apart they were. She decided then and there that they should end the relationship before it got any more serious. This was a punch to the gut for Michael and needless to say, he didn't handle it well.
This nearly broke Michael.
17 Michael Never Got Over Holly After They Broke Up
There was a significant amount of time between Michael and Holly’s breakup to their reconciliation. But throughout that entire time, it seemed like everything always led back to Holly for Michael.
No matter who Michael dated, or how he saw Holly seemed to have moved on, he still couldn’t get over her and frequently wished she hadn’t been transferred and that they were still together. It's understandable that most people would have a hard time getting over a breakup, but for Michael, he felt like he couldn't let go of who he thought was the love of his life. Turns out, he was right not to.
16 Darryl Witnessed Their Breakup
On the doomed road trip to Nashua from Scranton for Holly’s transfer, Michael wasn’t the only one in tow. Darryl - our favorite warehouse worker - was the one to actually drive them there.
He inevitably witnessed the demise of their relationship, and it was just as awkward as you would think. He took it all in stride, because that’s just how Darryl is, but he also provided some comedic relief when it was much needed. Even so, we're sure he wished he had been anywhere but there.
15 They’re Both Star Wars Fans
While Holly and Michael are definitely dorky, their love of Star Wars actually makes them one of the most relatable couples on the show. The first time they make a Star Wars reference was on the first day they met.
When Holly mentioned she could sit a certain way because she does yoga, Michael begins speaking like Yoda from the Star Wars franchise. He then laughs awkwardly and says, “YoDA”. Holly doesn’t miss a beat and begins talking like Yoda herself. It was a sickeningly cute moment between the two future lovebirds.
14 Michael Told People They Were Engaged - After They Broke Up
Michael Scott can be an enigma at times. He also is an attention-seeker and makes stupid mistakes because of it. A prime example of that was when he and Holly had just broken up, and instead of informing the office of this, he tells them all he’s engaged instead. You heard that right: engaged.
It only served to make things that much more awkward and embarrassing for him, so we’re not really sure what he was hoping to get out of telling that lie.
13 He Made Her A Mixtape
Once Michael knew he was falling for Holly on that first day they met, he decided to woo her the old-fashioned way: he made her a mixtape.
Or a mix CD, as it were. He began this process that day while in his office, and wanted it to work on “two levels.” He told Jim, “The two levels being “Welcome To Scranton” and…”I love you.” It was adorable, really. But also probably not the most appropriate thing to do with a new co-worker. Michael just couldn't seem to help himself.
12 They Became A Fan-Favorite Couple
Over the course of the series, fans had their favorite couples they preferred on the show. There was, of course, Jim and Pam. Then there was Dwight and Angela. But then, there was Michael and Holly.
Fans found the way Holly affected Michael and made him a better man than he already was was truly heartwarming to see. Watching their relationship unfold made it that much sweeter. They were the epitome of the dorky, endearing, perfect couple everyone wanted to see on their television screens each week.
11 Holly Wrote A Letter To Michael That She Never Sent
After the sad ending to their blossoming relationship, Holly moved on with her life in Nashua - or so it seemed. Even though she had a new boyfriend, while Michael was at her branch for a lecture, he noticed a letter addressed to himself on her computer.
So he did the only logical thing he could think of: he put the letter on his USB drive. He never read it, though he wanted to. But Pam did, and according to her it’s not completely over for Holly. The feelings were still there.
10 Pam Encouraged Michael To Not Give Up Hope With Holly
After Pam read that important letter Holly wrote, she not only told him that it seemed Holly still had feelings, but even seemed to encourage him not to give up hope when it came to her.
This likely came from her own relationship problems she initially had when it came to Jim. From her own experience, she knows if it’s meant to be, it will work out. It looks like she saw that was the case for Michael and Holly, too.
9 Holly Stayed With Her Boyfriend Even Though She Had Feelings For Michael
Once Holly and Michael ended their relationship, Holly felt she had to move on and did so in Nashua. She met a salesman there named A.J. and they dated for quite a while.
While they were together, it was obvious she still had feelings for Michael. Besides the letter she wrote, any time they were around one another there were sparks flying. It made you wonder why she still stuck with A.J. when Michael and her were a much better fit.
8 They like PDA
Public displays of affection can be a tricky thing. When it’s appropriate and not appropriate is not always cut and dry, but the workplace is probably not the best place to engage in some PDA.
But when Holly and Michael got back together for good in season 7, they couldn’t keep their hands off each other — literally. They were going all around the office being disgustingly cute and handsy which made everyone else feel uncomfortable. It didn’t seem to bother them, though.
7 They Did A Skit Together At The Company Picnic That Went Horribly Wrong
At the end of season 5, there was a company picnic thrown for Dunder Mifflin where all of the branches got together, including Scranton and Nashua.
This meant that Michael and Holly would be reunited. And though Holly had a new boyfriend, A.J., Michael still wanted to woo her during their skit. The skit they ended up performing in front of all of the branches, though, went so horribly wrong that it nearly ruined the entire picnic.
Luckily, it didn’t affect their friendship, and Michael accepted the fact that she was not with him again — yet.
6 He Threw A Toy From Her Then-Boyfriend Away Out Of Jealousy
Everyone remembers Woody from the Toy Story franchise. The toy, it turns out, was also a beloved gift that Holly’s then-boyfriend, A.J., gave to her.
When Holly returned to the Scranton branch in season 7 with that toy in tow, Michael was irrationally angry and jealous over her relationship with A.J. His reaction? To throw her treasured toy in the trash. Probably not the best decision but was pretty typical for Michael.
At least he cleaned him up after all was said and done out of guilt.
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