Spin City (1996)

S2E4 The Goodbye Girl

Michael attempts to convince the Mayor to reconsider his budding romance with Jennifer, a significantly younger woman. While grappling with his own relationship issues, Michael finds himself the target of Jennifer's flirtations. At the same time, Paul, relishing his role as Michael's aide, struggles to hire the most qualified candidate, Stacy Paterno, as he becomes increasingly attached to his current position.