: Alyssa Milano guest stars as Mayor Randall Winston’s rebellious daughter, Meg. She returns home after dropping out of law school with a "loser" boyfriend, prompting the Mayor to ask Caitlin (Heather Locklear) for help in getting through to her.
In the Spin City episode (Season 5, Episode 17), Deputy Mayor Charlie Crawford (Charlie Sheen) finds himself caught between his old carefree ways and his developing feelings for Julia. [S5E17] Rain on My Charades
: By the end of the episode, the dynamic shifts; following advice from his colleagues, Charlie realizes he is ready for a committed relationship, but Julia decides she is not. The episode originally aired on February 28, 2001, on ABC. "Spin City" Rain on My Charades (TV Episode 2001) - IMDb : Alyssa Milano guest stars as Mayor Randall