Richard hires a gospel singer (Jennifer Holliday) to perform at his uncle's funeral; Ally invites John on a double date, which ignites his insecurities. John: Peter MacNicol. Richard: Greg Germann. Ally: Calista Flockhart.
Ally tries to shed her innocent image by betting she can tell a dirty joke in front of an audience at the bar better than Renee. Rabbi Stern: Jason Blicker. Renee: Lisa Nicole Carson. Ally: Calista Flockhart.
A divorcée (Brenda Vaccaro) needs Ally's help to persuade her rabbi to make her separation legal in Jewish law. Meanwhile, the rabbi makes Ally an unexpected offer. Rabbi Stern: Jason Blicker. Jason: Andrew Heckler.
Billy confesses to Ally that he is not completely over her, which leads the one-time lovers to set personal boundaries so they can work together. Meanwhile, Georgia and Ally try to find a way around a prenuptial agreement for a client who is being divorced by her wealthy husband for another woman. Marci: Christine Rose. Jason: Stan Ivar. Billy: Gil Bellows. Ally: Calista Flockhart.