After arriving at work to propose a story about plastic surgery, Jack's mood turns unexpectedly ugly. Ordered to leave her father alone, Maya and her colleagues look for what could have suddenly caused his mood to sour. And after ruling out a possible health problem, Maya begins to suspect her dad is having an affair. Meanwhile, Finch is surprised when a fellow employee suddenly responds to his suggestion that they go out on a date. While Nina uncovers a problem with some alterations Jack wanted made to an old school jacket, a look at a photograph on his desk convinces Maya that her suspicions of an affair are justified. Between Elliot's close scrutiny of the photo and a search of his phone messages, Maya concludes that he's involved with a waitress named Rhonda. Meanwhile, Finch realizes he's being played for a fool after Courtney asks him to pick up an old boyfriend at the airport. After tracking her down at the Brooklyn diner where she works, Maya and Elliott discover that Rhonda is actually an elderly waitress who has been serving her dad and some friends since they were classmates in high school. And after Rhonda reveals that Jack's depression is a result of an annual gathering of his old pals that has failed to materialize for the first time in forty-five years, Maya takes matters into her own hands. Finally, after Nina manages to get the prized jacket repaired, she, Maya and the others arrive to help Jack make his annual walk across the Brooklyn Bridge.