Every Michael Scott Love Interest on The Office, Ranked From Awkward to Adorable

Michael Scott's dating history on 'The Office' is a wild ride—awkward, sometimes a little tragic, and, at times, completely hilarious. He started out basically as the world's worst boss (season one Michael is tough to rewatch), but somehow, over the years, we all came to root for him as he fumbled through relationships with a mix of real women, crushes he would never meet, and—sure, why not—his own temp employee. Let's break down Michael's greatest (and not-so-great) love interests.

Michael Scott's Greatest Loves—Ranked by Chaos and Cringe

• Katy Moore (Amy Adams): Remember Amy Adams showing up in season one as the 'Hot Girl' with handbags? Michael went into full cringe mode, proving just how insufferable he was back then. Katy wisely ditched him for Jim. Bullet dodged.
• Margaret (Brooke Dillman): Post-Jan heartbreak, Pam set Michael up with her landlady—who, unfortunately for Margaret, met Michael at his most awkward. He fakes his way through the start of the date, then gets bluntly rude when he realizes she's not his dream girl. Painful to watch, but kind of classic Michael.
• The Chair Model (Deborah Shoshlefski): Yes, this is a real entry, because Michael got obsessed with a random woman in an office catalog. The joke? She was already dead . Michael's deeply weird romantic standards hit a high point here.
• Donna Newton (Amy Pietz): The bar owner from 'Happy Hour'. Michael meets her after launching into his unbearable 'Date Mike' routine. She likes him anyway, but then it turns out she's engaged—and he's the affair. Michael thinks this is honestly kind of cool, but nobody else in the office agrees, and, predictably, it ends in chaos.
• Ryan Howard (B.J. Novak): No, it's not romantic, but Michael's crush on 'the temp' is legendary. Growing a beard to match? Declaring, 'I would have sex with Ryan' during office games? Michael's over-the-top hero worship is one of the show's persistent gags.
• Helene Beesley (Linda Purl): Definitely peak awkward—Michael dated Pam's mom. They actually seemed pretty happy, until Michael (of course) freaked out about her age and dumped her, on her birthday, in front of Pam. Even for this show, that was rough.
• Carol Stills (Nancy Carell): Played by Steve Carell's real-life wife. Michael and Carol met over a condo sale, then started dating for real in season two. It was promising until Michael tanked it by proposing way too soon. Carol bailed, and who can blame her?
• Glove Girl (Katie Aselton): One of Michael's rare almost-romances. He met an actually nice mystery woman donating blood, but after he passed out, all he had to remember her by was a pink glove. He turned the search for her into his own mini-epic love quest—totally on-brand, and kind of sweet/sad.
• Jan Levinson (Melora Hardin): This one gets the 'most infamous' award. Jan started as Michael's boss and tried to keep things professional—lasted about five minutes. Their relationship quickly spiraled into power games and chaos, peaking with the infamous dinner party for which the word ‘trainwreck’ doesn’t even seem adequate. Poor Michael.
• Holly Flax (Amy Ryan): Finally, Michael meets his match. Holly's just as weird, and their chemistry is obvious from the start. Even after setbacks—the Jan detour, Holly's transfer to Nashua—they find their way back. By the finale, Michael’s married to her and has a bunch of kids (he returns briefly to Dwight’s wedding as a happily ever after cameo). Frankly, it’s the ending Michael deserved.

The Bottom Line

Michael Scott's romance resume is a case study in cringe comedy, but somehow it works—and honestly, it's a big reason why he went from being one of TV's most annoying managers to someone you'd actually root for. His disastrous dates (and delusions) made his eventual happy ending with Holly all the sweeter.

'Never, ever, ever give up.' — Michael’s words might have been cringe, but you sort of have to admire his commitment.

Who's your pick for Michael’s greatest love? Personally, I'm still stunned about Glove Girl. Let me know if any of his failed romances should get more credit—it's not like there’s a shortage of options.