Heartbreak City

First Airdate: January 20, 1999

Episode number 31 Episode 2.09 Written by: David Simkins Directed by: Michael Zinberg Guest Stars: Lochlyn Munro (Jack Sheridan) Clayton Rohner (Drasi) Michael Reilly Burke (Cupid) Tiffany Salerno (Cindy) Brody Hutzler (Max) Jonathan Aubé (Kevin)