Michael Scott’s Love Interests, Ranked The Talks Today

In season one of The Office, Michael Scott (Steve Carell) was one of the most detestable characters on the show. Constantly showing his insensitivity to his employees, and just being a character, we couldn’t connect to him in any way, shape, or form. But as the show went on, Michael became a lot more endearing, showcasing his sensitive side and a lot of character growth which ultimately turned into one of TVs greatest characters.

Along his journey, Michael fell in love many times. To women he had just met, and even in some cases to women he will probably never meet, a trait that makes us love his harmless character so much more. From the likes of Jan Levinson, Holly Flax, Glove Girl and of course, Ryan Howard, here are Michael Scott’s best love interests.

Related: The Office: Best Projects From the Actors


10 Katy Moore

Katy Moore - The Office
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Played by the great Amy Adams, Katy Moore made her first appearance in season one’s “Hot Girl” episode, selling handbags in the office, where she immediately caught Michael’s eye. Michael was of course, inappropriate, which led to many awkward, yet hilarious moments between the two. Michael never really stood a chance, and we are glad he didn’t, as we previously mentioned season one Michael, was fairly irritating. Michael unsurprisingly, never got to go on a date with Katy, who instead, went on to date Jim Halpert (John Krasinski) for a while.

9 Margaret

Margaret - The Office
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After suffering from his heartbreaking separation from Jan, who we will get to later, Pam (Jenna Fischer) sets Michael up on a blind date with her landlady. Michael is excited to meet Margaret, but is sadly disappointed considering his fondness for the chair model scenes before, in one of the most awkward encounters on the show. Micheal pretends he is someone else to begin with, and then is just plain rude for the rest of the date. Margaret, played by Brooke Dillman, seems lovely, but to Michael, she isn’t “hot”, and leads to a hilarious date, of which Michael isn’t interested in, in the slightest.

8 The Chair Model

The Chair Model - The Office
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While searching through an office supply catalog, Michael immediately grows enamored with an attractive chair model, also known as Deborah Shoshlefski. Michael sits there for hours, staring at the chair model and tasks the rest of the office with fixing him up, and suggests that the chair model is a “template” of who he is looking for. Of course, this doesn’t pay off how Michael wants, and as Dwight (Rain Wilson) does his research, we find out that the chair model is in fact dead, after getting stoned and crashing into an airplane. Sorry Michael, but it just wasn’t meant to be.

7 Donna Newton

Donna - The Office
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In the season six episode “Happy Hour”, Pam and Jim set Michael up with one of Pam’s friends, and don’t tell Michael it’s a date, for good reason. When Michael finds out it’s a date, he puts on his irritating yet hilarious Date Mike persona, where he eventually meets Donna, the owner of the bar the entire Scranton office goes to in the episode.

Donna, played by Amy Pietz, is a wild character who strangely took a liking to Michael. However, we later find out that Donna is actually having an affair. But in a brilliantly hilarious twist of fate, it turns out Donna is having an affair with Michael, cheating on her husband. Michael obviously thinks this is cool, of course, but the rest of the office are not so keen, as they start rearing their heads at their manager. The two do eventually split, but their relationship was fun while it lasted.

6 Ryan Howard

The Office Ryan Howard
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Ryan Howard (B.J Novak), better known as “the temp” or “fire guy”, had Michaels attention right away. Of course, there was nothing sexual between the two, but Michael’s constant admiration of the young business tycoon was a joy to watch on screen. Michael grew a beard after him, hired him for the Michael Scott Paper Company, and even said he would “have sex with Ryan” during a game of “who would you do?” in “The Fire” episode. No matter if Michael meets the woman of his dreams, there is always a place in his heart for Ryan.

5 Helene Beesley

Helene Beesley - The Office
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Michael has had an assortment of girlfriends, but none were as surprising as when we found out that Michael was in fact dating Pam’s mom. Michael and Helene seem to have a great relationship, and both cared for each other, to the chagrin of Pam, who slaps Michael for dating her mom. When on a double date with Jim and Pam for Helene’s birthday, however, Michael finds out how old she actually is, and then has a strange meltdown, due to him not wanting to be with an older woman, which leads Michael to break up with Helene on her birthday in another incredibly awkward encounter. We think Michael and Helene would have been great together, but Michael couldn’t get over the age gap.

4 Carol Stills

Carol Stills The Office
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Carol, played by Nancy Carell, Steve Carell’s actual wife, is one of Michael Scott’s earliest love interests. Michael first met Carol when she sold him his condo, but the two didn’t actually begin dating until later on in season two. The two began dating in the brilliant episode “Casino Night”, where both Jan and Carol turned up to see Michael. Carol and Michael had a good run, but the relationship sadly ended when Michael prematurely proposed to Carol during “Diwali”, where she said no, and the two of them quickly ended things.

3 Glove Girl

Glove Girl The Office
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The story behind Glove Girl is actually kind of tragic. Imagine meeting someone you click with straight away, only for them to just disappear for good, with no name, phone number, or any trace of who they may be, barring a pink glove. During a Valentine’s Day blood drive, Michael donates some blood, when he meets a nervous woman next to him. The two hit it off, that is until Michael passes out. Michael then wakes up, and quickly looks over for the woman, but to his disappointment, it’s the office building’s security guard, Hank (Hugh Dane), sitting in her seat. Michael does, however, find her glove, which sends him on a quest to find the glove girl and return her glove back.

2 Jan Levinson

Jan - The Office
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Jan Levinson is arguably Michael’s most infamous love interest, whose illicit affair leads to a controlling and manipulative relationship. As Michael’s boss, at first, Jan attempts to keep things professional, but their relationship quickly turns into a loving relationship. At least during its early stages, as we soon discover Jan’s manipulative ways, of dumbing down Michael’s personality, and even forcing him to have two jobs, while she sits at home and drinks wine, and hosts awkward dinner parties.

Related: The Office: The Funniest Episodes in the Series, Ranked

1 Holly Flax

Holly Flax The Office
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Never has there been anyone as childish or as eccentric as the great Michael Scott; at least that’s what we thought. But upon Toby’s (Paul Lieberstein) farewell, we got to meet the love of Michael’s life, Holly Flax, played by Amy Ryan. The two hit it off straight away, telling stupid jokes and doing terrible impressions. From there, Michael was so infatuated with Holly that he immediately attempted to make a playlist to tell Holly he loves her.

Sadly, it takes a while for the two to inevitably be together, as Michael decides to help Jan through pregnancy, even though it’s not his baby, Holly moves to Nashua, where she meets her future fiancé. Thankfully, the two do end up together, eventually getting engaged in one of Michael Scott’s most endearing moments, and later in season nine, a season and a half after he left, Michael returns for Dwight’s wedding, where it is revealed that he is happily married to Holly, and the two have four kids together. We couldn’t think of a happier ending for Michael.

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