Streaming services like Netflix and Peacock continue bringing classic comedy series like The Office to new and old fans alike. While the hit NBC series has been off the air since 2013, it continues to be one of the most rewatched shows thanks to online streaming services. A lot of that support from fans is due to their love for the main character Michael Scott.
Michael Scott managed the Scranton branch of Dunder Mifflin Scranton. The Office followed his daily life as he tried to be the best boss and find love. Michael Scott had quite a few different love interests on The Office before he found his happily ever after. Some were perfect for him while others were toxic, and a few might have worked out if Scott had just given them a chance.
12 Jan Levinson Was Michael Scott's Most Toxic Love Interest
One of Michael Scott’s earliest and longest-lasting relationships was with his boss, Jan Levinson. She was also one of the most disliked characters on The Office. Michael Scott and Jan Levinson first got together after a successful sales meeting with a client, and their relationship secretly blossomed.
Jan Levinson was on a downward spiral when she began dating Michael Scott. She lost her job with Dunder Mifflin and moved in with Michael which contributed to their toxic relationship. She tried to change Scott’s personality, which ultimately made him miserable. They argued constantly and she manipulated his feelings for her. Both characters did much better in life after they broke up.
11 He Fell For A Chair Model Named Deborah Shoshlefski
Michael Scott reached a new low when he fell in love with a chair model from an office supply catalog. In one of Michael Scott's creepiest moments, he began imagining a future with a woman in a magazine that he knew nothing about.
This led Dwight Schrute, Assistant to the Regional Manager, to research the model to learn more about her. He discovered that her name was Deborah Shoshlefski, and she died in an automobile accident. Scott visited her grave so that he could move on from his "loss."
10 Michael Scott Developed A Crush On Purse Vendor Katy
While he didn’t often allow vendors in Dunder Mifflin, Michael Scott changed his mind when he first met Katy Moore. She was a handbag saleswoman who he asked to set up shop in Dunder Mifflin’s conference room for the day.
Michael Scott developed an infatuation with her immediately, and he attempted to woo her with fancy coffee and anecdotes about his goal to write a book. He seemingly secured a possible date in his eyes when she agreed to a ride home. However, Jim decided to ask Katy out as well. She went with him instead, crushing Michael's spirits temporarily.
9 He Couldn’t Tell Nikki From Benihana Apart From Her Friend
Michael Scott crashed hard after his numerous breakups, so his employees often tried to cheer him up. When he broke up with his realtor, they took him to Benihana to make him feel better. Michael Scott invited a waitress named Nikki back to one of Dunder Mifflin's many Christmas parties after a bit too much saké.
Nikki came along with her friend to the party, where Scott tried to impress her by giving her a bicycle from the toy donation. Unfortunately, he couldn’t tell Nikki apart from her friend and marked her with a felt pen. Nikki and her friend left after shooting down Michael’s further advances, and he laughed with his friends about the odd evening.
8 He Never Gave His Blind Date Margaret Much Of A Chance
Michael Scott went on a couple of blind dates in The Office, though they weren’t his preferred way to meet people. After his breakup with Jan, Pam set Michael up on a blind date with her landlady, Margaret. They agreed to meet at a coffee shop, though Scott ignored her description completely and started looking for the wrong woman.
When Margaret introduced herself, Michael Scott pretended that he wasn’t there to meet her. However, the barista called his name and they started their awkward blind date. Michael was rude to Margaret because of her age and looks, and even negatively compared her with his ex-girlfriend. They understandably never saw each other again.
7 Michael Was The Other Man When He Dated Donna Newton
When Michael Scott first met Donna Newton, he was actually on a blind date with another woman. However, he started acting foolish, which led the bar’s owner Donna to nearly kick him out. Oddly enough, they then bonded over business discussions and a mutual attraction.
Their relationship became physical after she came to Dunder Mifflin to buy a printer. He made a number of awkward advances until she finally revealed her feelings as well. Unfortunately, Michael Scott soon learned that she was married, and he was the other man. He ended the relationship after advice from his employees.
6 His “Date Mike” Persona Ruined The Blind Date With Julie
Pam and Jim tried to set Michael Scott up with their friends on more than one occasion. They invited Michael along with them to a bar to meet their friend, Julie. The night was going well since Julie laughed at every joke Michael told. However, things unraveled once Jim revealed to Michael Scott that he was on a date.
Michael stopped acting like himself and instead adopted his “Date Mike” persona. He quickly turned Julie off with his wild antics that tried way too hard and nearly got him kicked out of the bar. Michael Scott's "Date Mike" character ruined what could have potentially been a good match with Julie.
5 Scott Shared A One-Night Stand With Marie The Concierge
Michael Scott headed on a business trip to Winnipeg after a bad breakup. Andy and Oscar joined him on the trip, and they tried to help him meet someone new. He was told to ask the hotel’s concierge for help finding a good time while in Winnipeg.
Michael Scott developed an interest in the hotel concierge Marie, who was one of The Office's best single-episode characters They met up later at the bar she recommended to him, 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 He Connected With An Unknown Woman While Giving Blood
Michael Scott didn't get a chance to learn much about the mysterious woman he met during the blood drive in Dunder Mifflin's parking lot. Known to fans only as “Glove Girl,” she made an impression on Michael Scott when they were both struggling to give blood.
He was able to help calm her down with his jokes while she did the same for him. It seemed like there was a possible connection building, though he passed out after seeing blood. When he awoke, all that was left was the glove she had left behind. He held a singles luncheon at Dunder Mifflin to find her, but their missed connection was never further explored.
3 Scott Dated Pam’s Mother Helene Until He Learned Her Age
Jim and Pam were definitely the main romantic focus of The Office. Their romance often took the spotlight away from Michael Scott’s own attempts to find love. However, he found a new love interest at their wedding when he met Pam’s mom, 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 learned Helene’s true age at the birthday lunch, and he awkwardly broke up with her.
2 He Scared His Realtor Carol Stills Away When He Proposed
When Michael Scott decided to buy his own condo, he worked with realtor Carol Simms. Steve Carrell portrayed Michael Scott on The Office, and his real-life wife Nancy Carrell played Carol Stills. This helped fuel the fireworks between their characters.
Michael Scott and Carol Stills eventually started dating on The Office after a few meetings. He even asked Carol to join him at Dunder Mifflin’s disastrous "Casino Night," which was also attended by Jan Levinson. While they seemed to fit well together, Michael Scott moved too fast and proposed to her after only a few dates, scaring her away.
1 Holly Flax Complemented Michael’s Unique Personality
While Michael Scott usually had a contentious relationship with Dunder Mifflin’s HR representatives, everything changed when he met Holly Flax. She took over as Dunder Mifflin’s HR rep when Toby Flenderson briefly left The Office.
Holly made an impression on Michael Scott immediately by going along with 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 Office's most iconic episodes.