A divorced father and a soon-to-be divorced mother meet and begin a romantic courtship which is always complicated by their respective children and their own life problems.
A boy in the play school play asks Jesse out. Grace is less than happy with the news, because she thought that the boy was flirting with her during rehearsal. Karen is upset that Rick didn't left her out of the loop on this. Les takes over a talk show after the host leaves following an argument between the two. He asks for Lily's opinion on a call (while on the air), which leads to her taking over the show that night, and a once-a-week gig after that. Rick and Lily argue about her discussing Jesse's ""date"" when it hasn't been decided if he'll let her go. Grace thinks about quitting the play (over her sorta-feelings for Tad and the whole Tad-Jesse thing), but that's not what she tells Mr. Dmitri. He convinces her to stay. Grace is irate that Lily offered to loan Jesse Lily's pearl necklace when she wouldn't let Grace borrow it earlier. Grace is starting to think that Lily likes her stepdaughter Jesse more than her. Karen accuses Lily of using Jesse's personal life for radio ""mat
When Eli loses his job and Grace's teacher questions her acting, they both learn the hard way that real self-confidence can be one of life's toughest accomplishments. Both learn that tough love can be a powerful motivator.
A tragic accident shakes Karen from her deep depression and sets her up for the toughest battle of her life. This makes Eli and Jessie learn the hard way that their parents are more fragile than they'd thought.Watch Now:Amazon
Rick and Lily face more life-altering decisions when he is offered a major architectural position in Australia and she is offered a chance to take her Chicago-based radio show into national syndication. The Series Finale Episode concludes with this show's traditionaly black and white breaking of the fourth wall but this time, its the actors and not the characters as they speak about the realtionships formed amid the cast and what the show has meant to them.Watch Now:Amazon
Karen finds out that a grand jury is being impaneled to investigate the Atlantor project. The District Attorney wants Karen to help them, but she is reluctant. She acts nervously around Rick and refuses to discuss the investigation with him. Rick is subpoenaed to appear before the grand jury investigation of Atlantor. Allegations of bribery and arrests are floated about. Lily forces Christie not to print an unsubstantiated story concerning the grand jury. Rick fills his kids in on the situation. He finally talks to Miles, but Miles doesn't give him any assurances or definite answers. However, he does reveal that he has cancer, and it's advancing throughout his body rapidly, so he might not be around if the case goes to trial. Rick undergoes five hours of questioning by the grand jury. The episode ends with the Cook County sheriff arriving with a search warrant to search Rick's apartment...
Parental pressure bears down on Eli to get his act together for college. However, Eli wants to form a music group.
Grace doesn't know what to make of her new teacher. Judy asks Lily to work at her planned bookstore/cafe. Lily also interviews at a radio station. Karen brings up the idea of hiring Jake to work on the bookstore/cafe. Lily isn't sure about that idea or where she wants to work. She gets hired at the radio station, so she has a decision to make. Jessie becomes increasingly annoyed by Grace and Eli's behavior when they're around each other. Judy and Lily argue about working together. Judy and Jake resolve the dispute they had the day before and Jake agrees to work on the bookstore/cafe. Will tells Judy that he found his daughter in Florida and that he's moving there to get to know her again. Eli becomes the subject of Grace's journal entries. Judy finally realizes that she has to do the bookstore/cafe without Lily.
Jessie and Grace both audition for the same role in a school production of ""As You Like It."" Mr. Dimitri throws them a curve when he announces that he is planning a musical version of the play. Judy and Sam Blue spend the night together and Lily suspects there is something going on. Judy would like a real commitment from Sam, but he's not quite ready yet. Grace tells Mr. Dimitri that Jessie can't handle the stress of the play because of her eating disorder and eventually lands the lead role.
Lily Manning, separated from her husband, and Rick Sammler, divorced for 3 years, meet by chance when her daughter, Grace, injures her ankle in a soccer game. They go out on a date, and are instantly attracted to each other.
Rick and Lily's families gather at the school carnival. Lily and Karen, who don't know of each other at this point, are paired to work together in a booth there.
Rick and Lily celebrate their engagement. Tiffany reveals to Grace that she's pregnant, but Grace pretty much had that figured out when she heard Tiffany throwing up in the bathroom. Lily and Rick tell their kids about the engagement, and Rick and his kids moving into Lily's house. Lily finds out Tiffany is pregnant. When Rick tells Karen about his engagement and move, she seems less than thrilled. When the rooming arrangements are discussed, not everyone is happy with the decisions. Disagreements about where to put things come up also. Rick and Jake put a hole in the wall for a possible bay window, Lily gets upset at Rick for ""making all of the decisions,"" assuming she'll just go along with them. A family meeting at the end of the episode resolves a few issues.
Lily and Rick begin their wedding plans and want Judy to help, but Judy seems hesitant. Jesse faints and falls in the girls' locker room. Grace learns of it and voices her concern to Judy. Judy tells Karen, who tells Jesse, and argument ensues. Dr. Rosenfeld tells Rick and Karen to put restrictions on Jesse's activities until she eats what Rick and Karen ask her to. Jesse, of course, doesn't like this either. Judy reveals to Jesse that she was bulimic when she was younger. Judy finally blurts out that she doesn't trust Rick enough to watch Lily get married to him. Karen makes the decision not to let Jesse go on the ski trip with her classmates. This makes Jesse even more upset. Judy and Rick settle, somewhat, their differences. Dr. Rosenfeld makes Karen realize that she can't control every possible aspect of her and Jesse's life. Lily and Judy make up, and Karen lets go enough to allow Jesse to go on the ski trip.
Rick and his kids start to move their stuff to Lily's and Lily gets a call to sign the divorce papers. Carla tells Eli that she's not going back home because she's convinced that her parents hate her. So Eli asks Grace to ask Lily about staying at Lily's house. Eli gets his reply from the University of Illinois about admittance, and it's not good. Lily's hesitant about Carla staying with them. Eil tells his dad about the letter, at the dinner table, and neither one of them is happy now. Carla is worried that her plans to travel in Europe in the summer might not happen. Lily discovers medicine missing from her cabinet. Suspecting Carla, she goes to Carla's bag and finds them. Carla confesses to Rick about the pills. Lily goes to visit with Carla's stepmother and finds out some reasons for her problems. Carla tells Eli, in the middle of school, that she is leaving town immediately for Portland, Oregon. Eli says he wants to go with her. They plan to meet at the bus station that night. Ric
As the wedding approaches, hardly anything is finalized. Lily's father appears to her in her dreams. He asks her to ask Jake ""what's been lost"". Grace gets a letter from Carla, who's living with her brother, saying that she misses Grace, but not Eli. Grace lies to Eli and says Carla does miss him. Rick finds out that he's really low on cash and his attorney asks about scaling back the wedding plans. ""What's been lost"" is Jake's restaurant. He tells Lily this when she goes to pick up the cocktail napkins. Judy finds out details about Will's past through Tiffany, like that he has a daughter he gave up for adoption. Disagreements about who's staying where and who's paying for what prompt Lily and Rick to call off the wedding. Eli finds Carla's letter. Jesse calls Karen to tell her that the wedding is back on, and Karen sheds a tear. Jesse knew that her mother was secretly hoping that Rick wouldn't go through with the wedding. Lily's mother surprises everyone by showing up. Lily sees her aWatch Now:Amazon
Grace pursues her teacher and Jessie develops an attraction for her friend Katie.
Judy turns the bookstore into a ""book club for singles."" This attracts an interesting clientele, including Jake (who's tiring of his girlfriend Tiffany) and Lily's boss Christie. Judy isn't sure of her attraction to the handyman who's fixing up the store.