Jim from the office is dating
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.
However the company's plans change when Stamford regional manager Josh Porter accepts a job at Staples.
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.
Upon the merger of Scranton and Stamford branches, he becomes Assistant Regional Manager, and later co-manager alongside Michael Scott during the sixth season episode arc from "The Promotion" to "The Manager and the Salesman".
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.
Jim's misfortunes are assumed to be because he is unable to get over Pam.
However, things begin to look up for Jim as he befriends salesperson Karen Filippelli in Stamford, and when the company board of directors decides to close the Scranton branch, Jim is named Assistant Regional Manager of the newly created "Dunder Mifflin Northeast".