Though The Office primarily focuses on the happenings of Dunder Mifflin, it’s not without its expansive line of subplots. One of these side stories — which drives much of the series — is Michael’s endless quest for love.
In fact, Michael has multiple romances throughout the series. And though not everyone lasts beyond an episode, they’re all worth diving into. After all, without his long string of relationships, Michael might not have ended up with the woman of his dreams.
Its time to slow it down in Scranton; Here is a ranking of Michael Scott’s serious girlfriends, casual dates, and old flames.
Updated on April 28th, 2020 by Alyssa Avina: The Office is a show that stands the test of time, which is why we keep going back for a re-watch time and time again. Over the course of the series, we see Michael Scott repeatedly trying to find “the one” but instead mostly dates and is interested in people who are completely wrong for him.
Let’s take a look back at his disastrous dating history and crushes with this definitive ranking of them all.
Jan Levinson
Michael’s relationship with Jan is arguably the most explored of the bunch, with Jan first appearing in Season 1 and continually being referenced through the remainder of the series.
As Michael’s boss, Jan at first maintains a professional relationship with him. She constantly tries to get ahold of his antics, but eventually, she gives in to his affections and turns things toxic.
She is manipulative and controlling, which leads her to spend Michael’s money and grow lazy. Though she has never been kind to Michael, he still feels responsible for the child she conceives after visiting a sperm bank. Thankfully, he learns to let go.
Ryan Howard
It was no secret that Michael had a seemingly not-so-innocent admiration for his protégé Ryan Howard. It always bordered on an inappropriate crush he had on Ryan, even if Michael would deny this until the day he dies.
They obviously were not ever going to work out, but Michael had a tendency to toe-the-line of workplace appropriate behavior with his favorite employee. Ryan took advantage of his favoritism repeatedly which only further proves that they were not a match made in Dunder Mifflin heaven.
Nikki
Nikki is the Benihana waitress who is Michael’s date to the holiday party at the office in “A Benihana Christmas.” He gives her the bicycle he was going to donate to the poor as a gift and ends up confusing her with her friend Amy (who is Andy’s date) at the party. Clearly, she was about as memorable to him as their short-lived relationship.
What could Michael have expected, though? Carol had just broken up with him for photoshopping his face onto that of her ex-husband in her family’s ski trip photo. Rebounding was not a good idea.
Donna Newton
Donna was one of Michael’s more major relationships, though it wasn’t the slightest bit healthy. He first meets Donna in “Happy Hour” (S6E21) at the bar she manages, where she asks him to stop dancing on the pool table. Despite a rocky beginning, they flirt with each other and eventually begin a relationship with after she visits the office.
Unfortunately for Michael, he starts to believe Donna is cheating on him, only to find out that she is married and using him to cheat on her husband. Though it is difficult for him to break off the relationship, he sends Donna a text message officially ending things after getting pressure from his co-workers.
Margaret
When Michael decides he wants to get back in the dating game, he asks all of his employees at Dunder Mifflin to write down a woman’s name and number on a card in the hopes they would set him up with his ultimate match. Pam pities him and decides to actually try to set him up with someone — her landlady, Margaret.
She thought she was sweet and kind and would be a good date for Michael. But when Michael meets her for their blind date, he clearly is unattracted to her and unfortunately, makes that known to her, as well. It was mighty cringe-worthy.
Katy
Yes, Katy became Jim’s girlfriend, but she started out as Michael’s one-episode love interest. In fact, most of the guys at Dunder Mifflin showed attraction toward her.
As a purse vendor, Katy sells handbags in the office conference room. However, Michael is enamored by her and continually makes attempts to win her affections. He offers her a ride home after work, but ultimately gets rejected when he learns that Jim is heading out with Katy instead.
There was never much hope that this relationship would work out, but it was entertaining.
Pam Beesly
Pam Beesly never dated Michael in actuality, but if you listened to Michael’s story to Jan, you would think otherwise. As we learned in the infamous “Dinner Party” episode of The Office, Michael had been telling Jan for some time that he and Pam had previously been an item.
Pam, of course, vehemently denied this allegation only to have Jan — and Angela — not believe her. It was hilarious, sure, but Pam was not too happy about this turn of events. We can’t exactly blame her, either.
Deborah Shoshlefski
In “Chair Model” (S4E14), Michael is supposed to be picking out a new chair but instead becomes fascinated with the woman showing it off in the catalog. Unfortunately, Dwight does research and learns that she died in a car accident.
In order to get some closure, Dwight takes Michael to her gravesite at which they sing “Bye-Bye, Miss Chair Model Lady” to the tune of “American Pie.”
Though Michael and Deborah never met, you can’t say he wasn’t dedicated for a hot second.
Concierge Marie
Marie is the concierge Michael encounters on his business trip to Winnipeg with Oscar and Andy. He misunderstands what her job is and believes she is actually a “classy” prostitute.
Still attempting to move on from Holly, Michael takes a liking to Marie and gets excited when she invites him back to her hotel room. However, nothing real develops out of their brief relationship.
A deleted scene from “Sex Ed” (S7E7) shows Michael calling a concierge to tell her to get tested for herpes. Though the woman sounds nothing like Marie, it is assumed she is who he is trying to reach.
Glove Girl
After breaking up with Holly, Michael donates blood in the parking lot on Valentine’s Day. There, he meets a female donor whom he gets along with. However, he passes out because he didn’t eat enough food before giving blood, and when he wakes up, she is gone. He finds only a glove in her place and hopes she will return to retrieve it — though she never does.
It’s a romantic memory — after all, their blood bags touched. Too bad it couldn’t have become something more.
Julie
Julie is set up by Pam and Jim to go on a date with Michael. It initially goes well, since Julie laughs at everything and Michael enjoys her attention. But when he learns it’s an actual date, he turns on his “Date Mike” persona and it immediately goes awry.
Julie seemed like a nice enough woman, she was pretty and laughed at all of his jokes, so if he hadn’t ruined the date and met Donna that night, they might have been a nice couple to watch.
Helene Beesly
Pam’s Mom and Michael briefly date, and when Pam learns that a relationship has formed between the two, she goes crazy. Though she at first deems the relationship inappropriate, she later accepts that she can’t change it and goes out to lunch with Michael and Helene for her birthday in “Double Date” (S6E9). However, when Michael learns Helene is turning 58-years-old, he dumps her because he feels he is “robbing the grave.”
Helene may be sweet, but her relationship with Michael was never meant to last.
Carol Stills
Carol, who is played by Steve Carell’s real-life wife (Nancy Carell), is introduced as Michael’s real estate agent in “Office Olympics” (S2E3). She mistakenly believes Michael and Dwight are in a relationship with each other, but actually ends up dating him herself.
In “Diwali” (S3E6) Michael ends up proposing to Carole during a party, but she declines stating that it is only their ninth date. Things go downhill from there, and he doesn’t reconnect with Carol until Season 7 when he believes she has given him herpes.
Holly Flax
Holly tops off the list, as the woman Michael ultimately gets married to. Though their inconsistent relationship lasts throughout many seasons, they eventually learn they are perfect for each other in every way. To quote Jim, “Holly is kind of a major dork.” He meant it in the best way possible, implying that Holly’s and Micahel’s quirky personalities fit together like magic.
It is revealed in the finale that Michael and Holly are doing well together. Michael needs two phones to hold all the pictures of Holly and his kids.