Michael Scott certainly wasn't the ladies man he thought he was throughout The Office, but he did have a few solid relationships before settling down with Holly Flax (Amy Ryan). Steve Carell portrayed the central character before leaving Greg Daniels' NBC sitcom in the midst of season 7. As the regional manager of Dunder Mifflin's Scranton branch, Michael served as the man in charge. Though he was a good salesman, he wasn't always emotionally equipped to lead the workplace since he prioritized personal relationships over bettering the business. Michael's romantic relationships also had a habit of affecting his focus on work.
Based on his difficult childhood, Michael grew up dreaming of having his own family someday to make up for what he missed. When The Office started, Michael was around 40 years old, and he never gave up his goal of finding a woman to settle down with. Eventually, Michael realized that HR rep Holly was "the One," but he was forced to stay patient until she recognized that fact. In time, the pair ended up together, allowing Michael to finally have his happy ever after. Before they could go off to marry and have a house full of kids, Michael moved to Colorado with the love of his life, leaving his Scranton connections in the rearview. Though Michael received the chance at having his own family, it took a few failed relationships before Holly.
While Michael attempted to go on as many dates as possible to bolster his social life, Michael dated four women before proposing to Holly. In addition, there were a few brief flings during his time on the comedy series. First, there was the on-again-off-again relationship with Jan Levinson (Melora Hardin), Michael's corporate boss from Dunder Mifflin. While Jan tried to keep their relationship a secret, the rest of the company eventually found out the truth. Jan was later fired from the Dunder Mifflin, resulting in her decision to move in with Michael. As seen in season 4's "Dinner Party" episode, a lot of tension started to emerge between the couple. Based on Jan's poor treatment, Michael finally found the courage to break-up with her before she got pregnant with the help of a sperm bank.
Whereas Jan was Michael's longest relationship before Holly, Michael also spent some of the early seasons with Carol Stills (Nancy Carell), the real estate agent that sold him his condo. Michael moved rather too fast with Carol, proposing to her in public and photoshopping his face on her family's Christmas card. These actions scared her off, leading to their destined break-up. After failing to meet a single woman at Jim and Pam's wedding, Michael ended up starting a relationship with Pam's mom, Helene Beesly (Linda Purl). Pam was already upset with the situation, but Helene's age emerged as a turn-off for Michael. After that, he dated Donna Newton (Amy Pietz), a married woman who worked as the manager of a local bar. Being the "other man," Michael finally listened to his morals and ended things.
Other than the four relationships with potential, Michael had a few short romantic flings on The Office. There was the Chair Model girl in season 4 in addition to "Concierge Marie" from his business trip to Winnipeg the following season. Of course, Michael also had his sights set on the girl at the blood drive, but he never managed to reunite with her after passing out. Thankfully, Michael found his match in Holly, and the two presumably lived a fulfilling life together.
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