Carter discovers an old love letter written by Stuart. He decides to set Stuart up with the addressee of the letter, a woman who turns out to be Stuart's ex-wife. The woman quickly manages to set a whipped Stuart into his old rut. Meanwhile, Caitlin hires an image consultant when the mayor's approval ratings go down. The consultant discovers that the mayor has a problem with women, causing Charlie to make himself over. And also, Paul worries that he's unrecognizable.
Quest roles:
Kaitlin Hopkins, Joanna Going, Rosie O'Donnell(Rosie O'Donnell), Bob Glouberman(Reporter), Monique Edwards(Focus Group Woman #1), Naomi Serotoff(Focus Group Woman #2), Frank Mancini(Man in Focus Group)