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1-63 of 63
- Lily says that the kids in the two families should meet. So they schedule a night for that. Zoe is concerned about the environment. Grace again has conflicting feelings about Eli. Jennifer reveals to Grace that Cassidy is cheating on Eli. Grace is hesitant about telling Eli this information. Two of Cassidy's friends, Rachel and Lisa, warn Grace not to tell Eli what's going on (or else!). Naomi starts a book group and invites Karen, instead of Lily to be in the group because she feels that she and Lily have been drifting apart. Miles lets it be known to Rick that he doesn't want David involved on his project. Work pressures threaten to unravel Lily's plans for the meeting and they leave Rick on edge. Judy and Karen have a heart-to-heart in the bookstore about their two families. Eli finds out for himself that Cassidy's been cheating on him. Pressure from Miles forces Rick to cancel the dinner. A passage from the book the group is reading makes everything clear to Lily and Rick and Karen.
- Lily faces the reality of being on her own and Judy begins to pull away from her Lily. This happens after Rick offers to remodel the bookstore and Judy feels like the "odd man out" because Lily and Rick's relationship, she feels, leaves her little time to spend with Lily.
- Aaron returns for an extended stay and impresses everyone with his improvement. Grace and Spencer go back to the restaurant to write about their experience there, but Spencer gets nervous (because he was scared then) and goes home. The voices that have haunted Aaron for so long return at dinner and he freaks out. Shelley returns and says that despite the dinner outburst, he is getting better.
- When Lily's brother Aaron expresses a desire to move out on his own with a young woman who is also mentally disabled, she finds it emotionally impossible to let him go.
- 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.
- 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.
- 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 realise 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.
- 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 about her attraction to the handyman who's fixing up the store.
- Lily Manning, separated from her husband, and Rick Sammler, divorced for three years, meet by chance when her daughter, Grace, injures her ankle in a soccer game. They feel an immediate attraction. They date but family problems interfere: Rick's son Eli is having trouble academically and Lily's daughter Grace feels unpopular and unattractive. Rick and Lily are embarrassed when her children catch them entwined on the couch.
- As the two families merge into one house, disagreements over Jesse and Zoe's room decorations dominate the breakfast discussion. Lily's employer, Pages Alive, shuts down, so she's out of a job. Eli's busted for marijuana possession following a car accident. The officer finds Coop's marijuana in the car. This renews Karen's demands that Eli get a job and give up music. Lily, however, has a different opinion. Karen also talks with Rick about Eli living with her for a while. Predictably, Rick gets caught in the middle. Rick finally stands up to Karen and says that Eli will be okay. In the end, Eli ignores his mother's wishes and gets a job in a recording studio and continues to live with Rick and Lily.
- Karen pushes herself far beyond her comfort zone when her involvement with Leo becomes more serious. Eli plays his parents against each other in order to get into a bar to see his friends' band play. He gets in trouble when he sees his mother and she sees him there. Rick finds out that Karen said no and Eli didn't tell him that, getting Eli in trouble with Rick as well.
- 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.
- Lily and Karen both have unrealistic expectations for Thanksgiving celebrations. So naturally, nothing goes as planned. The lighting board at the theater goes out, so rehearsal is postponed. Lily does all the cooking herself after the kids are all busy. The pipes underneath the sink rust out, so that messes things up further. Judy doesn't want to be at dinner if Sam is coming (via Rick's invitation). Disagreement over building plans leads to Rick and Sam working on Thanksgiving, which upsets Lily even more. Karen is depressed about not having anyone to celebrate Thanksgiving with.
- Lily hires a divorce attorney. The last straw is after Jake reneges on his promise not to max out their credit card. She finds this out after it's rejected at a store. Grace meets a boy who seems to think like her.
- A boy in the 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 "material."
- As Valentine's Day approaches, Rick and Karen are battling over the Atlantor project. Things come to a head when Karen manages to get an injunction stopping work on the project and David quits the firm. Grace's protest of the Atlantor project adds to Rick's problems. Rick and Lily finally manage to get together for Valentine's Day but neither of them is happy with the way things turn out.
- The prospect that Grace may be romantically involved with her creative-writing teacher troubles Lily, infuriates Jake, and imperils the career of the instructor.
- Jessie's anxiety and guilt about her mother's slow recovery causes tension with every member of the family, especially Lily. Meanwhile, Eli is in denial about the seriousness of his mother's condition.
- It's Thanksgiving and that means the Sammlers and the Mannings get together for dinner, whether they want to be there or not. It turns out that the two mothers get along quite well. It's Rick and his mom that have issues. She questions whether Rick knows that his children aren't doing as well as he would like to think. Barbara sees her son Aaron for the first time since Phil's funeral.
- Jesse is taken to a psychiatrist to find out why she isn't eating. Karen's firm is hired to oppose the building of Miles' building -- the one that Rick is designing.
- Will returns to repair ice damage to Lily's house, making for awkward moments for Judy. Judy runs into Paul (the guy who went off on her when she broke it off with him), creating more awkwardness for Judy. Lily grows agitated with Graham's constant flirting with the office women. Judy tells Karen that she thinks that Paul is the one calling her late at night. When Jake finds out that part of the repair might include a workspace for Rick in the attic, he says that he won't pay for the repairs. Judy hears noises outside her store and calls Jake. Jake confronts Paul and tells him to stay away from Judy and assaults him in the restaurant's kitchen. Lily angrily tells Graham that he has a real problem when dealing with women. Lily was going to give Tiffany Grace and Zoe's old baby clothes, but decides to save them for Judy's future kids. Will reveals to Judy that it was he who was doing the calling and the noises. He angrily tells her she was wrong to dump him, among other things, which totally humiliates Judy into apologising for her behaviour towards him.
- 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.
- Parental pressure bears down on Eli to get his act together for college. However, Eli wants to form a music group.
- The women (and Grace and Zoe) want to hold a baby shower for Tiffany. This doesn't excite Jake. He doesn't want Grace - and especially Zoe - to have expectations about him and Tiffany. So Jake discourages the idea of having Zoe at the shower. So she calls Lily to cancel the shower, which upsets Zoe. Jake tells Tiffany that she shouldn't go home to have the baby just because of him and Zoe. Lily convinces Tiffany to have the baby in Chicago and to have the shower also. Jake wants Lily to butt out of "his business", but because the kids are involved, he relents. Judy goes to her doctor to see how many "baby years" she has left. She even tells Lily that she's considering in-vitro fertilization. Zoe is upset over Jake's seeming indifference about his upcoming baby. Jake goes ballistic in front of all the women and kids when he and Zoe get home and the ladies discover that he didn't get a gift. Lily reassures Jake that he is still a good father despite his outburst. Jake does go to the shower with one of the gifts that Zoe wanted. Jake explains his situation with Tiffany to Zoe, who seems to be okay with it.
- Sam returns to town, further complicating the lives of Judy, Lily, and Rick. Sam wants to hire Rick to be the architect for a project he has. Judy, however, wants to hire Rick to redo her bookstore. Colin is agitated over Sam's inability to produce any sketches. Jake grows increasingly worried with the impending arrival of his and Tiffany's baby. Fearing he's having an anxiety attack, Judy tells him to go see her doctor. Colin gives Rick an ultimatum: Sam better produce some sketches, or else Rick and Sam will be fired. So Rick lets Sam know how serious the situation is. Jake's test results are clean and Sam comes through. Sam and Judy agree that now isn't the right time for them to be together.