Jesse doesn't want to go to a dance by herself, which frustrates Karen because they bought a dress for it. Christie and Graham continue to clash at work. Karen's worried that her relationship with Leo isn't building towards something. Lily is uncomfortable with Graham's flirting and when she goes to establish that their relationship is purely a working one, he confesses his feelings for her. Rick interrupts him before anything else can happen. When she tells Christie, Christie basically tells her it's no big deal. Later, Graham kisses Lily unexpectedly. When Leo shows up late for a museum trip with Jesse, Karen is really upset with Leo because she knows that Leo means a lot to Jesse. She finally decides to break up with him. Lily angrily confronts Graham about it, with Christie present.

Layoffs at her workplace make Lily even uneasier there. But the new management consultant reverses those firings, putting Christie on edge and making Lily look foolish for speaking up at a staff meeting. Christie fires Lily for meeting with Graham behind her back. Judy accuses Lily of taking her BookLovers idea and using it for the magazine at work. Zoe feels abandoned because Grace doesn't want to baby-sit and stay home all of the time. In the end, the investors liked Graham's presentation, and Grace and Zoe (and Lily and Judy) make peace with each other.

Lily and Rick try to blend their families together, but it doesn't go smoothly. Jesse has trouble adjusting to high school.

Changes in the design of Miles' building that Rick's firm are designing means a dinner meeting for Rick - and a reluctant Lily -- with Miles and important clients. When Lily puts her two cents worth in at the dinner, it makes for an awkward evening for Rick.

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

Rick and David are served with a notice to get an injunction to stop the Atlantor project - and the hearing is on Valentine's Day. Grace is troubled by the fact that a building that is helping those who need help is being torn down to build Miles' (and therefore Rick's) project. David is frustrated that no one but him thinks that they have a serious problem with the project and the injunction to stop its construction. Rick sees Grace protesting and they have an argument. David quits the firm because of his opposition to the project. The court's decision makes no one happy, with the possible exception on Miles. Rick proposes to Lily, but she feels it's not the right time.

Jake gets into trouble with his business. A small fire at Lily's house causes a lot of worry. Karen struggles with Eli's moving into the basement.

Judy finds herself drawn between two men: the intellectually stimulating Paul, and the physically stimulating Will. Eli grows tired of Carla always wanting to get into trouble.

Tensions between Benny (a busboy) and Giancarlo (the chef) at Jake's restaurant boil over. Jake separates the two and tells Benny to go home. He returns with a gun to confront Giancarlo. But he isn't there and can't be reached, so Benny holds everybody hostage. Over the course of the night, Tiffany hands Jake some surprising news, Grace and Spencer (who's there for his grandma's 75th birthday) become closer, and Lily realizes her feelings for Rick and accepts his proposal. At the restaurant, at the end of the night, Benny lets everyone go... and then puts the gun to his head...

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.

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.

Lily and Rick deal with the ghosts of their failed marriages. Rick's becoming consumed with a project at work triggers Lily's memories of Jake doing the same thing in their marriage, causing its downfall. Meanwhile, Eli's frustration with his schoolwork reaches new depths.

Lily and her family cope with a life-altering accident.

Flashbacks in the series' interview style recall a telling incident in the lives of Rick, Karen, Sam Blue's estranged wife Jeannine, and Sam himself, who rues another dalliance. Also, when Sam and Judy's relationship becomes the talk of the whole family, Sam finally realizes he wants Judy to be more than just a friend. Meanwhile Karen's loneliness and discomfort is compounded when Jessie cancels plans with her mom to stay at Lily's house.

Just when Lily thinks life can't get any more complicated, her mother begins to show early signs of Alzheimer's disease.

Jake and Lily begin mediating their divorce, and the future of the house hangs in the balance. Meanwhile, Rick struggles with a demanding client, complicating his partnership with David. At Jennifer's insistence, Grace fills in as an English tutor for Eli, and the two discuss Lily and Rick's recent breakup. Rick arrives at a decision regarding his future with Lily.

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.

Lily's new job helps her put her priorities in order. While talking to Grace, Tiffany lets it slip that her relationship with Jake started BEFORE Lily and Jake split up, possibly altering her relationship with her father forever.

Grace gets her learner's permit. She has a crush on Pace, a boy from her driver's education class, who seems oblivious to her feelings. So she goes out with Paces' annoying friend, Spencer, in an attempt to maybe make Pace jealous enough and have him ask her out. The date is a disaster. Tiffany breaks up with Jake when it becomes clear to her that their relationship wasn't going to go beyond the physical attraction.

Lily thinks she might be pregnant, and the reaction she gets from Rick wasn't what she was hoping for. She begins to think that he's not who she thought he was. Grace has an accident in Rick's vehicle after being distracted spotting Carla and Eli together. So Grace starts to rethink her opinion of Carla. The episode ends with Rick and Lily making up, and Eli and Carla in the back seat of a car...

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.

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...

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.

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 g

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.