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.

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.