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However the company's plans change when Stamford regional manager Josh Porter accepts a job at Staples.The Stamford branch then closes, with a few employees being offered a transfer to Scranton.This is presumably because, as Pam mentioned later, "everybody likes Jim".

After Dunder Mifflin is bought by Sabre Corporation, Jim is very briefly the sole regional manager of the branch, before returning to the Sales department until his termination in the series finale.

His reason is later stated as "It's just, I kinda put it all on the line. Throughout season 2, Jim dates Katy, who initially appeared in season 1 as the "Purse Girl" in "Hot Girl".

After Jim and Katy split up in "Booze Cruise", he leaves a message asking out a fellow Dunder Mifflin employee named Brenda, much to Kelly's disbelief.

Throughout the first two seasons, incidents such as Pam falling asleep on Jim's shoulder in "Diversity Day" and drunkenly kissing him in "The Dundies" show a possibility of the feelings being mutual; however, Pam never acts on them and she remains engaged to Roy.

On one occasion, in "The Fight," his flirting with her goes a little too far, when Meredith looks over to see him play-fighting with her, causing her to shut him down immediately, startling him with her abruptness, though she eventually forgives him.

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