The Office: 9 Times Michael and Holly Made Fans Cringe

While Michael Scott didn’t seem like a character who was destined to find a perfect match, Holly Flax ended up being right for him when his other girlfriends were not. Fans rooted for the couple and found their eventual engagement endearing. However, despite these two having many sweet moments, it’s also not surprising to fans of The Office that Michael Scott’s humor and behavior could be downright awful and give second-hand embarrassment to viewers.

Overall, Holly Flax was better behaved and less cringe-worthy than Michael, but even she had her awkward and even inappropriate moments. Together, as a couple, there were times when Michael and Holly made fans cringe just as often as they made fans laugh or smile.

9 Michael’s Treatment Of AJ (S5 Ep17)

Michael is not an emotionally mature character, so it’s no surprise he doesn’t know how to act when he meets AJ for the first time. While Holly isn’t even there at the Nashua branch, Michael has outbursts toward AJ, and, as time goes on, he often calls him names or is just downright rude.

Of course, Michael doesn’t often treat even people he likes with politeness, so this isn’t a big shock. However, it is often difficult to watch as AJ didn’t do anything wrong.

8 Michael Stealing Holly’s Letter (S5 Ep17)

When Michael finds the letter on Holly’s work computer, he downloads it to read. Given how immature Michael is, it isn’t surprising that he doesn’t have the impulse control to leave the letter alone, which does lead to him copying it onto a USB stick (it also seems like a plot device, seeing as most people wouldn’t write something so private on their work computer).

Luckily, Pam convinces Michael not to read it, but it is a breach of Holly’s trust and privacy for Micahel to take it in the first place. Who knows how Holly reacted when she saw it on the documentary. It would have probably led to a huge fight between them.

7 When They Made Darryl Help Holly Move (S5 Ep6)

After Holly is transferred to Nashua, Darryl ends up helping the couple move her stuff. The entire car ride is extremely awkward, and it’s hard not to feel bad for Darryl having to be in this situation.

Not only is he forced to listen to ‘Life is a Highway,’ on repeat but there are also a few tense moments as Holly and Michael debate several times about whether they should break up or not. Although the fans’ hearts went out to Michael and Holly’s dilemma, there was certainly a time and place for this conversation to take place.

6 Michael Insisting They Were Meant To Be Together (S7 Ep7; Ep14)

Micahel and Holly did click well, and they had a good relationship. However, they initially dated for a short time before Holly moved. The fact that Michael was so hung up on the idea that they were meant to be together after such a short relationship is rather odd (although on brand for Michael, who often dramatizes things).

However, it wasn’t entirely fair for him to continually express this to Holly, even when Holly was dating AJ. Micahel should have learned to not be so pushy and overstep the personal boundaries she had set.

5 Holly Making An Inappropriate Joke To Oscar (S5 Ep1)

While Holly might have had overall better people skills than Michael, she did a couple of things when she first joined the Scranton branch that were very cringe-worthy and inappropriate.

When talking to Oscar about dating, she said that maybe she should “switch to women” since she was striking out with men. It was an inappropriate joke to make in general but especially bad because Oscar himself was a gay man. Holly might not have meant offense, but she did stick her foot in her mouth.

4 Michael Destroying The Toy Story Woody Doll (S7 Ep11; Ep12)

Michael’s immaturity is a running source of comedy and embarrassment throughout the series. He will do things like try to frame Toby for drugs or take long naps at work, but this is one of his pettiest moments.

After Holly returns to Scranton, Michael destroys the toy because AJ gave it to her. It’s something that even young children would know not to do, and it also wasn’t a smart move if he wanted to gain back Holly’s trust. As expected, tension rose between the two.

3 Michael Not Caring About Business Ethics (S5 Ep3)

Overall, the entire episode with the ethics seminar gives some fans secondhand embarrassment. Although Holly was trying to do her job, she was met with a branch that had no real business ethics to speak of. Michael wanted Holly to brush the Meredith issue under the rug, and this led to a conflict between them.

When Michael threw away Holly’s leftovers because she disagreed, he was lashing out in his immaturity once again. It was certainly a significant milestone in The Office as it showed Michael and Holly might not have been as perfect as fans thought they would be.

2 Their PDA Problem (S7 Ep16)

When Michael and Holly are reunited in season seven, they really seem to fall hard for one another. They start kissing, cuddling, and even nearly making out at work in front of their co-workers, and everyone around them is uncomfortable.

Given that Michael was the manager and Holly was the HR rep, this breach of just overall social conduct was particularly weird to watch, and it did seem like they were pre-teens who didn’t know how to handle themselves in love.

1 Revealing The Closed Branch At The Company Picnic (S5 Ep26)

One of the few times Holly is seen after their first break up is when the duo put on a skit for the company picnic, but this leads to one of the most cringe-worthy moments from The Office. In their attempt to merge Dunder Mifflin with Slumdog Millionaire, they revealed that the Buffalo branch was going to be closing.

The fact that they disclosed this information to a bunch of employees in front of their families was so awkward, and it was hard for viewers to not want to yell at Michael and Holly for being so obtuse.

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