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A huge snowstorm traps everyone in the building overnight. Meanwhile, Portia convinces Katie that Chuck's romantically interested in her; and Carol saves the day when she breaks into the offices of their competitor and steals all the morning show's wine.

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.

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.

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.

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 has a midterm she must pass in order to keep her internship. Katie needs to choose between helping her mom and focusing on her hacking story, which she can't seem to crack. Meanwhile, Greg's wealthy estranged grandmother pays a visit to the office. Chuck finds her cold and cruel, but almost immediately falls in love with her.

Katie secretly investigates a celebrity phone hacking ring behind Greg's back. In Katie's absence, Carol falls into producing a piece on her favorite phone game, "Biscuit Blitz." Meanwhile, Chuck gets in hot water when Portia accuses him of mansplaining.