Caitlin hires an image consultant to determine why Mayor Winston's approval rating with women has plummeted. Stuart's overbearing ex-wife comes back into his life, courtesy of Carter's bungled attempt at matchmaking.

Randall's visiting daughter Meg decides to become a free spirit by dropping out of law school and moving south with her loser boyfriend. Charlie blows off a date with Julia to attend a sporting event with Stuart, Carter, and Paul.