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Katie's secret war reporter boyfriend, Trip, is back in town and working at the MMN offices. Despite Katie's best efforts, Carol quickly uncovers the covert relationship using a plan she stole from "Days of Our Lives". Meanwhile, Chuck, feeling threatened by Trip, is determined to return to the field. Greg and Justin support the idea until they find footage of Chuck's time as a war reporter in the '90s.

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.

Carol is excited when Chuck asks her to wait for the cable guy at his townhouse, until Chuck gives an ominous warning that tests her curiosity. Meanwhile, Portia's phone gets hacked and Katie struggles not to read her private emails.

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.

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 makes a huge discovery about the story she's been chasing and, with the help of Carol and the rest of the staff, concocts a scheme to get the story out. Greg struggles with balancing his conflicting loyalties to his family, co-workers and conscience.