Episode 28 of "Spin City"
s2e04 The Goodbye Girl
Title: The Goodbye Girl
Original Air Date: 10/15/1997 on ABC
Plot Outline:
Michael tries to dissuade the Mayor from a relationship with Jennifer, a much younger woman. However, as Mike deals with his own relationship troubles, Jennifer makes a pass at him. Meanwhile, Paul is acting as Michael's assistant, and enjoying it so much that he can't bring himself to hire the best candidate for the job, Stacy Paterno.