‘The Office’: How Many Girlfriends Did Jim Halpert Have in the Series Before His Relationship With Pam Beesly?

In the highly popular mockumentary series called The Office about the Dunder Mifflin Paper Company in Scranton, Pennsylvania, Jim Halpert (John Krasinski) and Pam Beesly (Jenna Fischer) weren’t always an item. Although years would go by before they made things official, even in season 1, it was obvious they had an attraction toward one another and feelings were developing. But before things became official between them, Jim had two girlfriends.

John Krasinski as Jim Halpert
John Krasinski as Jim Halpert | Paul Drinkwater/NBCU Photo Bank

Amy Adam’s Katy Moore in Seasons 1 and 2 of ‘The Office’

Amy Adams
Amy Adams | Paul Treadway/Barcroft Images Getty Images

The accomplished actor Amy Adams had a small stint in the series, appearing in three episodes in total. Her arrival to the series happens in season 1, episode 6 called “Hot Girl.” She sells her purses in the conference room when Michael Scott (Steve Carell), the Regional Manager, takes a liking to her. But it’s Jim who wins her over, and he offers to give her a ride home and they go for a drink, which upsets Michael, as he was going to take her home.

Jim and Katy form a new relationship, but things fizzle out because of Jim’s feelings for Pam, who is currently engaged to Roy Anderson (David Denman) at the time. After Roy sets a date for the impending nuptials, Jim and Katy watch the couple dance and kiss. Jim breaks up with Katy when she asks if that will ever be them. Jim’s feelings for Pam are undeniable, and he realizes that he cares about her, so he dumps Katy. However, more time will pass before Jim and Pam are together at last.

Jim Halpert and Pam Beesly kiss more than once

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Despite the undeniable connection between Jim and Pam, they won’t make things official until season 4. Pam kisses Jim while drunk in season 2, episode 1 called “The Dundies,” but she stays engaged to Roy, who she’s been with for years, until season 3 when we learn she canceled the wedding plans, according to Dunderpedia, The Office Wiki Fandom page. Despite Jim telling Pam his true feelings about being in love with her, she dismisses it, and they even share another kiss in season 2, episode 22 called “Casino Night,” which seems to lead nowhere for a while.

Karen Filippelli as Jim’s Girlfriend in Season 3

Rashida Jones in 'The Office'
Rashida Jones as Karen Filippelli in ‘The Office’ | Paul Drinkwater/NBC/NBCU Photo Bank/NBCUniversal via Getty Images

Jim takes a transfer to the Stamford, Connecticut branch of the company, and a major reason behind the change is the situation with Pam. It’s there that he meets Karen Filippelli (Rashida Jones) who works in sales, someone he’ll eventually start dating in season 3. When the Stamford office is closed though, Jim returns to Scranton with Karen as well. Jim tells Karen about how he feels about Pam at one point, but they continue to be together, which is kind of strange.

To top it off, Pam admits to Karen in season 3, episode 15 called “Ben Franklin” that she is in love with Jim. New developments emerge when Jim is honest with Pam about his feelings later on after she had already told him that she canceled the engagement with Roy because of him.

While Jim, along with Karen and Michael, interview for a promotion in a corporate capacity, Jim sees a note Pam left for him, and things change in season 3, episodes 24 and 25 called “The Job.” He heads to the Scranton office, totally ditching Karen. Finally, Jim asks Pam to go to dinner with him, and they finally start a relationship. Jim reportedly breaks up with Karen, and that was the end of things. She transferred out of Scranton as the Regional Manager of the Utica branch, and Jim and Pam became the happy couple we all know and love. However, Karen does return in an episode in seasons 4 and 5, and she gets married and has a child.

Jim and Pam become engaged in season 5, episode 1 called “Weight Loss.” And they marry at Niagara Falls in Season 6, Episode 4 called “Niagara.” The happy couple becomes a truly iconic staple in the series, and they go on to have two children together.