Lily Manning (Sela Ward) was a 40ish suburban soccer mom living in Deerfield, Illinois. Recently separated from her philandering husband Jake (Jeffrey Nordling), Lily was doing the best she could in the raising of her two daughters, insecure, anxiety-ridden 14-year-old Grace (Julia Whelan), and wide-eyed, innocent 9-year-old Zoe (Meredith Deane). Lily was a woman who, in her own words, had "always wanted to be safe." Now, for the first time in her life, she saw no clear direction as the life she had always imagined for herself and her family seemed to be slipping away. Although well supported by her younger sister, Judy (Marin Hinkle), at whose bookstore, called My Sister's Bookstore, she worked, she still felt very anxious about the future. Then, one day, she discovered an unexpected new possibility for herself when she met Rick Sammler (Billy Campbell) in the principal's office at Grace's school, Upton Sinclair High School.

Rick was a single father and co-head of an architectural firm, Sammler/ Cassili Associates, which was located in downtown Chicago. Rick had been divorced from his uptight ex-wife Karen (Susanna Thompson), for three years and had two children, Eli (Shane West), a 16-year-old basketball player at Sinclair High who suffered from a learning disability, and sensitive 12-year-old Jessie (Evan Rachel Wood), who longed for the days before her family's disintegration.

Lily and Rick shared an immediate mutual attraction and began dating. Their budding relationship caused problems in both of their respective families. Jake, who still maintained a close relationship with Lily's parents, Phil and Barbara (Paul Mazursky and Bonnie Bartlett on a recurring basis), was in the midst of remodeling and reopening their restaurant, Phil's, which they had left to him before retiring to Florida. His high level of continued personal involvement with them kept them from accepting Lily's relationship with Rick right away, even as Jake got them all into increasingly worse financial situations in his endeavor to get the restaurant up and running again. Grace strongly objected to Lily and Rick's relationship as she still hoped to see her parents get back together. Judy didn't care much for Rick, but still supported her sister since it seemed like no one else was going to. Karen, a public interest attorney at the downtown law firm of Harris, Riegert, and Sammler, was worried about the toll Rick's new relationship would take on their children, particularly Jessie, who was shy and emotionally fragile. She was also working through her own feelings of jealousy that Rick was moving on to a new relationship.

The stories presented on Once and Again explored the wonder and the difficulty of a second chance at love, as well as the family dynamics of divorce and subsequent remarriage, parent and child relationships, and the search for love, self-discovery, and personal fulfillment.

From: Wikipedia