Spin City - Season 1 - Eps 16: Kiss Me, Stupid
It's Valentine's Day, and Carter's old flame Spence wants to meet with him. Meantime, Mike goes on a date from hell with a beautiful friend of Nikki's, and Paul's romantic evening with Claudia becomes unforgettable for all the wrong reasons.
About Spin City

Title: Spin City
First Air Date: 1996-09-17
Last Air Date: 2002-04-30
Status: Ended
Rating: 7.05/10 (from 299 votes)
Language: EN
Seasons: 7
Total Episodes: 145
Network: ABC
Genres: Comedy, Drama
Production Companies: Ubu Productions, DreamWorks Television
Synopsis
Workaholic Mike Flaherty is the Deputy Mayor of New York City, serving as Mayor Randall Winston's key strategist and much-needed handler. Mike runs the city with the help of his oddball staff: an anxious and insecure press secretary; a sexist, boorish chief of staff; an impeccably groomed gay activist running minority affairs; a sharp and efficient, man-crazy accountant; and an idealistic young speechwriter. Like Mike, they are all professionally capable but personally challenged.
Cast

Charlie Sheen
Charlie Crawford

Heather Locklear
Caitlin Moore

Richard Kind
Paul Lassiter

Alan Ruck
Stuart Bondek

Michael Boatman
Carter Heywood

Barry Bostwick
Randall Winston