Season 1 Lily is in the process of divorcing her restaurateur husband, Jake. She is reluctant to begin dating again due to the sensitivities of her daughters, who are still emotional about the divorce. She meets and is instantly attracted to divorced architect Rick Sammler. However, their new relationship is complicated by Lily's many remaining emotional and financial issues with Jake. Lily must navigate the complicated worlds of divorce, finding herself in midlife, and reentering the workforce. She is able to find strength and resilience as she affirms her marriage to Jake is over, starts a new job as a publishing assistant at the magazine Pages Alive, and grows in her relationship with Rick. Grace and Eli become close when she becomes his tutor. Judy has a relationship with Rick's friend, Sam Blue (
Steven Weber) before discovering Sam is married.
Season 2 Lily and Jake's divorce is finalized and she hopes to spend more time with Rick. However, Rick becomes sidetracked by difficulties at work and has to begin working with unscrupulous developer Miles Drentell (
David Clennon, reprising his role from the series
thirtysomething). Things become difficult for Lily when Rick's project runs into legal difficulties and his ex-wife Karen is hired to represent the opposition. Jessie flirts with an eating disorder and begins to address her problems with the help of a therapist (played by show producer
Edward Zwick). Jake's girlfriend Tiffany announces she is pregnant. At the end of season two, Rick has to dissolve his architectural firm, and Lily and Rick get married.
Season 3 Rick resumes his partnership with Sam Blue, now divorced, to design a hotel for a new client. Sam and Judy try to be friends but eventually resume their romantic relationship. Jake and Tiffany have a baby girl and eventually decide to get married. Grace develops a crush on her English teacher, Mr. Dimitri (
Eric Stoltz); although their relationship never became sexual, an investigation eventually forces Mr. Dimitri to leave the school. Meanwhile, Jessie discovers she is attracted to another girl: upperclassman Katie Singer (
Mischa Barton), and after Katie acknowledges her own romantic feelings towards Jessie with a love letter, the two girls quietly begin dating while hiding their romance from everyone, in what became the first teen lesbian romance on American network television. Karen deals with her depression; just as she is starting to make progress, she is hit by a car, leading to months of painful rehabilitation where she meets physical therapist Henry Higgins (
D. B. Woodside). Lily faces more painful domestic struggles when her mother begins to show signs of
Alzheimer's disease and her brother Aaron (
Patrick Dempsey), who is schizophrenic, wants to move in with his girlfriend. By the end of the season, Rick and Lily face big decisions when he is offered a job in Australia and she is offered a nationally syndicated radio show. Their decisions are never shown, but in the last moments of the series finale, Lily reveals she is pregnant and everyone comes together to attend Jake and Tiffany's wedding. ==Cast==