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Every Michael Scott Love Interest In The Office, Ranked

Streaming services like Netflix and Peacock continue to bring classic comedy series like The office to new and old fans alike. Although the hit NBC series has been off the air since 2013, it remains one of the most-watched shows thanks to online streaming services. Much of that fan support stems from her love for lead character Michael Scott.

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Michael Scott led the Scranton branch of Dunder Mifflin Scranton. The office he went about his daily life while trying to be the best boss and find love. Michael Scott had quite a few different love interests in The office before finding their happily ever after. Some were perfect for him, while others were toxic, and some might have worked if Scott had given them a chance.

12/12 Jan Levinson Was Michael Scott’s Most Toxic Love Interest

One of Michael Scott’s oldest and longest-lasting relationships was with his boss, Jan Levinson. He was also one of the most unpleasant characters in The office. Michael Scott and Jan Levinson first got together after a successful sales meeting with a client, and their relationship blossomed in secret.

Jan Levinson was on a downward spiral when she started dating Michael Scott. She lost her job with Dunder Mifflin and moved in with Michael, which contributed to her toxic relationship. She tried to change Scott’s personality, which ultimately made him miserable. They argued constantly and she manipulated her feelings for her. Both characters did much better in life after they broke up.

11/12 He fell in love with a chair model named Deborah Shoshlefski

Michael Scott and his chair model from The Office

Michael Scott reached a new low when he fell in love with a chair model from an office supplies catalog. In one of Michael Scott’s creepiest moments, he began to imagine a future with a woman in a magazine he knew nothing about.

This led Dwight Schrute, Assistant Regional Manager, to investigate the model to learn more about it. She found out that her name was Deborah Shoshlefski and that she died in a car accident. Scott visited her grave so he could get over the “loss of her” of her.

10/12 Michael Scott fell in love with the bag saleswoman Katy

Michael Scott and Katy Moore from The Office

While he didn’t used to allow salespeople at Dunder Mifflin, Michael Scott changed his mind when he met Katy Moore. She was a handbag saleswoman who he asked to set up shop in the Dunder Mifflin conference room during the day.

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Michael Scott fell for her immediately and tried to woo her over fancy coffee and anecdotes about her goal of writing a book. He apparently secured a possible date from her in her eyes when she agreed to take her home. However, Jim decided to ask Katy out as well. She went with him in her place, crushing Michael’s spirit temporarily.

9/12 I couldn’t tell Nikki from Benihana apart from her friend

Michael and Andy with waitresses from Benihana at The Office

Michael Scott broke down long after his many breakups, so his employees often tried to cheer him up. When he broke up with his real estate agent, they took him to Benihana to make him feel better. Michael Scott invited a waitress named Nikki to one of Dunder Mifflin’s many Christmas parties after some sake.

Nikki came with her friend to the party, where Scott tried to impress her by giving her a bike from the toy drive. Unfortunately, he couldn’t tell Nikki from her friend and marked her with a marker. Nikki and her friend left after shooting down Michael’s new advances, and he laughed with his friends about the strange night.

8/12 He never gave his blind date Margaret much of a chance.

Margaret on a blind date with Michael Scott from The Office

Michael Scott went on a couple of blind dates in The office, although it was not his preferred way of meeting people. After her breakup with Jan, Pam set up Michael on a blind date with her landlady, Margaret. They agreed to meet at a coffee shop, though Scott completely ignored her description and started looking for the wrong woman.

When Margaret showed up, Michael Scott pretended he wasn’t there to greet her. However, the barista called him by her name and they began their awkward blind date. Michael was rude to Margaret due to her age and appearance, and even negatively compared her to her ex-girlfriend. It is understandable that they never saw each other again.

7/12 Michael was the other man when he was dating Donna Newton

Michael Scott and Donna Newton from The Office

When Michael Scott met Donna Newton, he was actually on a blind date with another woman. However, he started acting silly, leading Donna, the owner of the bar, to almost throw him out. Oddly enough, they later bonded through business discussions and a mutual attraction.

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Their relationship turned physical after she went to Dunder Mifflin to buy a printer. She made a series of awkward advances until finally she too revealed her feelings. Unfortunately, Michael Scott soon found out that she was married and that he was the other man. He ended the relationship on the advice of his employees.

6/12 His “Date Mike” persona ruined the blind date with Julie

Julie on a blind date with Michael Scott from The Office

Pam and Jim tried to set up Michael Scott with their friends on more than one occasion. They invited Michael along with them to a bar to meet his friend, Julie. The night was going well as Julie laughed at every joke Michael told. However, things fell apart once Jim revealed to Michael Scott that he was on a date.

Michael stopped acting as himself and instead adopted his “Date Mike” persona. He quickly turned Julie off with her wild antics trying too hard and nearly getting him thrown out of the bar. Michael Scott’s “Date Mike” character ruined what could have been a good pairing with Julie.

5/12 Scott shared a one night stand with Marie The Concierge

Marie the concierge from The Office

Michael Scott went on a business trip to Winnipeg after a bad breakup. Andy and Oscar accompanied him on the trip and tried to help him meet someone new. They told him to ask the hotel concierge for help finding a good time while he was in Winnipeg.

Michael Scott inquired about the hotel concierge, Marie, who was one of the The officeThe best characters from a single episode of They met later at the bar she recommended and he flirted with her. They had a one-night stand, though he was quickly kicked out of her room. Still, it was one of Michael Scott’s least traumatic relationships.

4/12 He hooked up with an unknown woman while donating blood

Michael Scott and Glove Girl donating blood from The Office

Michael Scott didn’t get a chance to learn much about the mysterious woman he met during the Dunder Mifflin parking lot blood drive. Known to fans only as “The Glove Girl,” she impressed Michael Scott when they were both struggling to donate blood.

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He was able to help her calm down with his teasing while she did the same for him. It seemed like there was a possible connection, though she did pass out after seeing blood. When he woke up, all that was left was the glove she had left behind. He held a singles lunch at Dunder Mifflin to find her, but her missing connection was never explored further.

3/12 Scott dated Pam’s mom, Helene, until he found out her age

Michael Scott and Helene Beesly from The Office

Jim and Pam were definitely the main romantic focus of The office. Their romance often took attention away from Michael Scott’s own attempts to find love. However, he found a new love interest at her wedding when he met Pam’s mother, Helene.

Helene Beesly and Michael Scott began a passionate love affair that quickly became a sore spot for Pam. However, she began to accept the fact that Michael was dating her mother and agreed to go out for lunch to celebrate Helene’s birthday. Unfortunately, Michael Scott found out Helene’s true age at her birthday lunch and broke up with her.

2/12 He scared his real estate agent Carol Stills when he proposed to her

Michael Scott and Carol Stills from The Office

When Michael Scott decided to buy his own condo, he worked with real estate agent Carol Simms. Steve Carrell played Michael Scott in The office, and his real-life wife, Nancy Carrell, played Carol Stills. This helped fuel the fireworks between his characters.

Michael Scott and Carol Stills eventually began dating on The office after a few meetings. She even asked Carol to join him at Dunder Mifflin’s disastrous “Casino Night,” which was also attended by Jan Levinson. While they seemed to be a good fit together, Michael Scott moved too fast and proposed to her after only a few dates, scaring her.

1/12 Holly Flax complemented Michael’s unique personality

Michael and Holly from The Office

While Michael Scott used to have a contentious relationship with Dunder Mifflin’s human resources representatives, that all changed when he met Holly Flax. He took over as Dunder Mifflin’s human resources representative when Toby Flenderson briefly left. The office.

Holly impressed Michael Scott immediately by accepting his hatred for Toby. They shared a similar sense of humor, and Holly seemed to be the only one who really understood Michael. While the relationship was put on hold after Holly was transferred, they found their way back to each other. They left together to start a new life in one of The officeThe most iconic episodes of .

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