Jacqueline Barrett ("Jack") abandons her unfaithful fiance at the altar, and heads to NYC (where her friend Audrey works as a dancer) to rebuild her life. Moving into Audrey's apartment, she encounters David Jillefsky ("Jill") who's preparing to move in with his girlfriend Elisa. "Jack" and "Jill" develop a hot and cold romantic relationship, but face obstacles in their relationships with their friends.
The main characters were David Jillefsky (Ivan Sergei) and Jacqueline Barrett (Amanda Peet, replacing Amelia Heinle after the pilot). The two become romantically involved just as they both face major obstacles in their relationships with their friends. The show's theme song was "Truth About Romeo" written by Pancho's Lament, the stage name of songwriter Jeff Cohen. It was performed by Pancho's Lament during the first season and by David Crosby and Beth Hart in the second season.
Due to the average ratings of the first season, the second season was only 13 episodes long and was aired as a midseason show. The final episode detailed the problems during preparations for the couple's wedding. Jacqueline discovered she was pregnant, but before she could tell David, he decided that their relationship was moving too fast and he wanted to call the wedding off and move things slower. Despite the rallying of fans, the series was not renewed for a third season, so the series ended in a cliffhanger.
Co-stars Amanda Peet and Sarah Paulson would later reunite for the NBC series Studio 60 on the Sunset Strip, which debuted in 2006.