Michael and Ryan have an interesting dynamic on The Office. Michael always cares about Ryan and believes the best of him, and Ryan doesn’t always return the favor very well, as he can be quite selfish. On the other hand, Micahel is also a person who doesn’t understand boundaries, which makes it understandable why Ryan gets annoyed with him at times.
One thing is for sure, however, and that’s that these two have a lot of hilarious moments together over the course of the entire series. We’ve put together a list of the 10 best moments between Michael and Ryan including the funny, awkward, and heartfelt.
In the episode called “The Deposition,” Michael’s journal is submitted as evidence. This episode is all about Jan’s case to sue Dunder Mifflin for firing her. When the journal is submitted, the lawyers ask who the person named Ryan is. As the journal says, Ryan is “just as hot as Jan, but in a different way.”
Of course, Ryan isn’t actually a woman but is instead Ryan Howard. The fact that Michael recognizes that Ryan is so attractive is pretty cute, to be honest.
Michael often thinks that Ryan is an extremely cool person. Ryan also thinks this about himself, too. While Ryan seemed like a pretty logical person at the start of the series, he becomes more delusional and full of himself as time goes on.
During the time when Ryan is at corporate, Michael is even more desperate to be pals with him in "Weight Loss." This leads to him growing a goatee just like Ryan’s after helping him move into his apartment.
This is another example of Michael thinking that Ryan is extremely attractive. It’s definitely endearing that Michael doesn’t have any issue talking about Ryan being hot, although sometimes he definitely needs to cool his jets and be more professional.
Many fans have even wondered if Michael could be a little bisexual since he is always talking about Ryan’s good looks. Plus, he also clearly wants to emulate what Ryan does all the time.
Ryan isn’t really a great person. He starts out not so bad in the series, but after he gets Jan’s job at corporate, he turns into a big jerk who is totally full of himself. When Ryan started the company, WUPHF, Michale and others gave him money to get it off the ground.
Instead of forcing Ryan to sell, Michael tells him he believes in him. This actually ends up convincing Ryan to sell the company, and it's a great example of Michael believing in Ryan even when he doesn’t deserve it.
Michael is always there to give Ryan another chance, even when Ryan hasn’t been a great friend to him. After committing fraud and being fired from Dunder Mifflin, Ryan ends up working at a local bowling alley in Scranton.
When Michael leaves Dunder Mifflin to start his own paper company, he saves Ryan from this job and offers him a sales job. It’s pretty clear that Ryan doesn't always deserve Michael’s help, but he definitely is lucky to have Michael.
Early on in the series, Ryan has Michael come to business school to be a guest speaker in one of his classes. He does so because it will give him a full letter grade boost in his class. Of course, this visit does not go that well. Other students in the class question Michael and suggest that Dunder Mifflin won’t be able to last more than a few more years.
Michael becomes really offended by this. This is one case where Michael gets the upper hand in their relationship as he ends up sending Ryan to the annex with Kelly in retaliation.
There are definitely a few times where Michael recognizes that Ryan isn’t a good friend to him and doesn’t have his back. While Michael sees himself as a mentor to Ryan, this dynamic changes when Ryan gets the corporate job and Michael doesn’t. Ryan becomes really full of himself because of this and Michael ends up saying this hilarious quote:
“We had a foreign exchange student living with us when I was young. And we called him my brother... Then he went home to what is now formerly Yugoslavia, taking all of my blue jeans with him. And I had to spend the entire winter in shorts. That is what Ryan is like. A fake brother who steals your jeans.”
In season two of The Office, Micahel needs to write Ryan a review so Ryan can send it to the Temp agency. This makes Micahel think Ryan is asking for his business advice.
He decides he needs to give Ryan his rules of business, which are unsurprisingly not that helpful. This entire exchange is pretty funny, and it's even funnier because it makes Dwight so jealous.
There are a few times in The Office where Ryan isn’t a complete jerk to his coworkers. One of these times is during the “Grief Counseling” episode when Ryan participates in a prank with Pam.
Ryan tells a story about his cousin Mufasa getting trampled to death by wildebeests, and Michael is totally unaware that he is just telling the plot of The Lion King.
While Ryan is always pretty clear that he thinks he’s too good for Michael and Dwight, things change when he is under the influence of drugs.
Michael and Dwight end up having a good, albeit hilarious time, partying with Ryan in NYC. This also gives some insight into the issues Ryan is having and shows that Michael does care about him.