"The Breakdown" gets a new boss, Diana St. Tropez, a tough business lady with big plans to bring their outdated news program into the 21st century. Katie is thrilled since this is exactly the kind of strong, professional female role model she hoped for, but Carol is immediately wary of this new influence in Katie's life. Meanwhile, Chuck has trouble adapting to Diana's idea for a new panel segment of screaming pundits.

Diana sets Katie off on a mission to take the job at the station that she wants, but when Katie tries to be executive producer for the day, she soon realizes that Greg has it much harder than she realized. Meanwhile, Carol uses Greg and Katie's workplace competition as an opportunity to push the two of them together. After Diana insults Portia on a women-in-business panel, Portia declares a "squad feud" that forces their two very different worlds together.

Diana has been promoted again, this time to the head of the corporation that owns MMN, but before she leaves she finds herself embroiled in a sexual harassment scandal. This leaves Katie unsure who to believe - her mentor or her friends in the office. Carol becomes head intern and struggles to prove to the other interns, and herself, that she deserves the job.

When the show is nominated for an American Journalism Award, Katie looks forward to spending the night with reporters she has admired her entire life; Chuck is eager to reunite with all of his old anchormen friends.

Katie tries to impress her friends by going to a hip Halloween party with Portia; Chuck is asked to use a new smart screen on the show but tries to get out of it by convincing Carol that it is possessed.

Katie is invited by Jeremy to do some real reporting; Carol is suspicious and kidnaps Greg to help her spy on them; Chuck bonds with Portia's fiancé.

Carol finds herself in a reverse "Christmas Carol" during which she learns that she has too much Christmas spirit and is driving everyone around her insane. Meanwhile, Chuck's estranged son, Petey, visits the office and Katie, who has been charged with babysitting him, tries to get the father and son to reconnect.

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Carol is devastated to learn that her parents are getting a divorce after 70 years of marriage. Katie, still hurting from her breakup with Jeremy, is convinced that love is dead, but Carol is determined to prove that it's never too late to have a happy ending. Meanwhile, Chuck discovers that the reason for Justin's newfound happiness is the cute new barista at the coffee shop and proceeds to compete for her affection at the expense of his and Justin's friendship.

Carol hatches a plan to get Katie to admit her feelings for her boss; Chuck finds himself an unwitting champion of the alt-right.

When "The Breakdown" staff finds themselves embroiled in a lawsuit with eccentric billionaire Fenton Pelt, Chuck is convinced he can solve the problem. But when Chuck's attempts to save the show backfire, he enlists the gang's help to pull off an elaborate heist. Meanwhile, after realizing that she has feelings for Greg, Katie is determined not to make a move on her unavailable boss. Her intentions are put to the test, however, when Diana St. Tropez demands that the two spend the night together fact-checking a story.

After an explosive fight with her daughter, Carol is excited about her new position at "Morning Wined Up," but is disappointed to realize that the job offers less responsibility than she had hoped. Katie is determined to bring down Fenton Pelt, the billionaire suing "The Breakdown," despite specific orders from Greg and the network's attorney to leave him alone. When Katie's rousing speech about journalistic integrity fails to inspire anyone but Chuck, who has been suspended from the show, she reluctantly joins forces, only to find that his investigative skills aren't what they used to be.