The journey of Michael Scott through The Office was littered with awkward interactions with women. Frankly, it was also littered with awkward interactions with men, children, and a few dogs. Fans of the series knew early on that Michael was not going to be lucky in love, thanks to a visit from a friendly purse seller. And the only way he could have made their interactions worse would have been literally setting her car on fire.

Michael Scott was simultaneously the most awkward and offputting human on the face of the Earth as well as being one of the most caring. And no one tried harder than him. His main problem seemed to be that Michael had a lot of love to give but really didn't seem to know how to express it even close to appropriately. This was certainly the case when it came to women.

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Virtually every interaction he had with a woman through the course of the series reached new and impressive levels of awkwardness. Unfortunately for the women who worked at Dunder Mifflin with him, they were often the recipients of that awkardness. This was a huge downside of being his assistant, something Pam had to live through on an almost daily basis. But being the focus of his romantic affections was even worse.

Michael and Dwight take Katy on a tour

Fans first got a good look at the horror show that was Michael having a crush on someone in Season 1, Episode 6. A woman named Katy Moore arrived at the office to sell purses. As she pointed out in the episode, her best customers were men buying presents for their girlfriends and wives. While she might have just been there for business, Katy also, unfortunately for her, caught the eye of one Michael Scott.

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As he was want to do, Michael decided to attempt to woo Katy. It went impressively badly, even for him. Michael was wildly unsuccessful in his attempts to help her sell purses. He took her on a tour of the office, something she desperately did not want to do. Then, when other men tried talking to her, Michael interrupted them, and often ran them off entirely. It got really bad when Katy tried to interact with Ryan Howard.

This episode set the tone for so many of Michael's relationships with women as the series went on. Nothing ever really seemed to go right for him, including his extended, difficult, and one-sided partnership with Pam Levinson. It wasn't until he met Holly Flax, the only person on the show who was as strange and awkward as he was, that his luck really changed. Once they finally got together, everything fell into place for both of them.

Katy Moore would go on to date Jim in Season 2 before they had an extremely messy breakup. She played a part in furthering the growing relationship between Jim and Pam, but she also helped define Michael's character. While his behavior around women he was interested in would only continue to get more and more ridiculous as The Office rolled along, his meeting with Katy gave fans a clear look at the absurdity they were in for.

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