‘The Office’: Holly Flax Was Never Supposed to Date Michael Scott

The Office might have been a comedy series about a paper company, but the show also examined interpersonal relationships. The “World’s Best Boss,” Michael Scott (Steve Carell), wanted nothing more than to find love. He eventually found his perfect match in Holly Flax (Amy Ryan), but not before getting put through the proverbial ringer. Ironically, showrunners on The Office never intended for Michael and Holly’s relationship to last. Here’s why. 

Michael Scott was looking for love in all the wrong places 

Michael Scott had several girlfriends throughout his time as Dunder Mifflin Scranton’s Regional Manager. He dated Carol (Nancy Carell), his realtor, who was put off by how quickly Michael progressed their relationship. 

Michael also dated Jan Levinson (Melora Hardin), his direct superior, who was actually a terrible match. He also had flings with Donna (Amy Pietz), Pam’s (Jenna Fischer) mother, Helene (Linda Purl), and Concierge Marie (Wendi McLendon-Covey), amongst others. But none were as perfect a match as Holly Flax. 

Michael Scott and Holly Flax made for the perfect couple 

Throughout The Office, Michael Scott had one goal — fall in love. Though he dated several women over the seven seasons he was on the show, finding his soul mate proved to be difficult.

The character of Michael Scott loved and craved attention. “Do I need to be liked?” Michael said during one of his hilarious talking heads. “Absolutely not. Do I like to be liked? I enjoy being liked. I have to be liked. But it’s not like this compulsive need to be liked, like my need to be praised.” 

When Holly entered his life, suddenly, Michael wasn’t seeking attention from anyone and anything anymore. He solely wanted to be recognized and celebrated by Holly. And he didn’t have to work hard to do that. That’s partly what made them such a perfect match.

Originally, showrunners had a different plan for Holly Flax 

Holly Flax joined the series at the end of season 4. She replaced Toby Flenderson (Paul Lieberstein) in human resources. Initially, because of her position, Michael had a distrust for Holly. But he quickly realized she was his dream woman. 

As Lieberstein explained to co-star Brian Baumgartner on his podcast, An Oral History of The Office, showrunners simply wanted to put someone next to Michael who liked him to “see how it [looked].” Originally, Holly was only written into six episodes. 

“The decision of Holly came out of the decision to evolve Michael’s character past Jan,” writer Jen Salata explained. The writers wanted to get Michael to a point where he found a partner and a peer. The difference between Holly and every other woman in Michael’s life was that she actually liked him. Also, Holly was just like Michael in a lot of ways. 

Ironically, Michael and Holly’s relationship became one of the strongest on The Office. 

Michael Scott and Holly Flax ended up living happily ever after 

Almost instantly, showrunners knew Holly and Michael were meant to be. Holly allowed Michael to grow as a character and ultimately end Carell’s time on the series in a way that made sense. 

“I think when you find true love, nothing else really matters,” Ryan told Baumgartner. “Eventually, [Michael] finds his true family.” And for him, that was Holly. 

In season 7, episode 19, Michael perfectly proposed to Holly. Together, they moved to Colorado to care for Holly’s aging parents and, ultimately, live out their happily ever after.