Spin City - Season 6 - Eps 18: An Affair Not to Remember
Caitlin takes a trip down memory lane and realizes that she and Charlie met years before and that he was the reason why she lost what might have been the best relationship of her life. Flashback to a preppy and conservative Caitlin and a cool, life-of-the-party Charlie at an old college bash. The flashback makes Caitlin realize that her current boyfriend, Tom, might not be right for her, and she ends up kissing Charlie! Meanwhile, the Mayor bartends at a fundraiser at which Paul is trying to pick up a woman, and the woman's friend has fallen for Carter, who is gay.
About Spin City

Title: Spin City
First Air Date: 1996-09-17
Last Air Date: 2002-04-30
Status: Ended
Rating: 7/10 (from 301 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