Karen Filippelli - Season 3

Season 3

Karen first appears in the Season 3 premiere, "Gay Witch Hunt". It is implied in a deleted scene that she was a likely candidate for Assistant Regional Manager before Jim arrived and got the job, causing her to feel somewhat threatened by him; she refers to him as a "major kiss-ass." She is initially annoyed by Jim's trademark mugging at the camera but later develops a crush on him.

The two share some flirtatious moments. Jim also helps her find some Herr's Salt and Vinegar potato chips, which she mentions are her favorite. In "Diwali", she gives Jim a much-needed ride home when Jim gets drunk at work with Andy and is unable to ride his bike. It is also shown she drives a Honda Passport.

In "Branch Closing", Karen is saddened when it seems that Jim is pushing her to move to New York City instead of Scranton—much like Jim's reaction to Pam in the episode "Halloween"—indicating he does not really care where she ends up. At the end of "Branch Closing", she admits to the documentary crew that she likes Jim, although at the time she does not think he likes her.

Karen manages to immediately hit it off with Pam. Later in the same episode, Jim tells Pam he was "seeing someone" (implying Karen). It was later confirmed in "The Convict" that Jim and Karen are dating. Phyllis commented to Karen in the episode "Traveling Salesmen" that she thinks Karen is good for Jim. Dwight remarked during a sales call to Jim that he finds Karen to be "pretty" and that she "appears intelligent".

In "A Benihana Christmas", after Pam admits she has been "cold" to Karen, the two leave the party planning committee to form their own party, becoming friends in the process. In "Back from Vacation", Karen thinks of getting an apartment two blocks away from Jim's. They get into a slight argument over this. Pam helps to mend their fight by advising Jim to "go easy" on Karen.

In "Traveling Salesman", Karen learns of Jim's feelings for Pam. When Jim initially denies Karen's accusation, she mentions that she moved from Connecticut (presumably for Jim), which prompts him to confess the old "crush" he once had for Pam. He admits that he told Pam before he transferred to Stamford and that she did not reciprocate. Karen seems relieved when Jim adds that he is glad she took the Scranton position.

In "The Return", Karen declines to play a prank on Andy with Jim. Jim ends up conducting the prank with Pam, which irritates Karen. She eventually confronts Jim about it, and asks him if he still has feelings for Pam, which he quietly affirms. This revelation seems to be taking a drastic toll on the two, as it is revealed in "Ben Franklin" that Karen is doing everything she can to keep the relationship afloat, while Jim is becoming increasingly uninterested. Karen did gain a small victory in the episode when Pam claimed that her feelings for Jim are non-existent. In "Phyllis's Wedding", Jim implies that he hypothetically would go out with Pam if she appeared to be interested. But after witnessing Pam leaving the party with Roy, he states a non hypothetical: That he's glad he's with Karen.

When Jim is invited as an assistant manager to a cocktail party at the house of David Wallace, Dunder Mifflin's CFO, in Mount Vernon, New York, Karen accompanies him and uses the occasion to prank her boyfriend. Throughout the evening, she frequently mentions to Jim that she had previously dated some of the male guests at the party. She later reveals that he was "kinda her first." When Jim shows surprise by this admission, Karen mentions, once again, how easy it is to fool him.

In "The Negotiation", Karen tries to convince Jim to go out on a date with her instead of staying home to watch a Phillies game. Karen remarks that when she learned about Pam and Jim's kiss, her response was to talk with him about their feelings while Roy's response was much more violent. Karen confesses that she does not know which reaction Jim "hated more". In "Women's Appreciation", Jim reveals that he is taking Karen out for their six-month celebration; Karen is seen buying sexy underwear from Victoria's Secret and Phyllis comments that Jim will love it, as Pam looks on sadly. It is revealed by Jim that Ryan asked Karen on a date a few months earlier, and Karen tactfully turned him down.

In "Beach Games", Jim chooses Karen for his team, which he names "Voldemort", to anger Dwight. During a lull in the games, Jim and Karen set up interviews for a position at corporate. Karen has an upset and almost disbelieving look on her face when Pam addresses the entire office to talk about herself and Jim.

In "The Job", Karen becomes increasingly adversarial towards Pam. Karen and Jim go to New York City a day ahead of their interview to enjoy the city. Karen makes it clear that if Jim gets the job, she would move to New York City to be with him, and that she expects the same from Jim should she get the job.