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.

Amid complete chaos, a surprise Christmas Eve delivery of Tiffany and Jake's baby unites the Manning and Sammler families like never before. Meanwhile, Judy's first encounter with Sam's eleven-year-old son doesn't go very smoothly.

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.

Grace finds an ""adult magazine"" in their home recycling bin. This leads to a whole ""will you talk to Eli about this?"" talk coming from Lily to Rick. Rick is amazed at Sam's continued inability to be with only one woman at a time. Judy and Sam have yet another awkward conversation, this time at a newsstand. Judy later confesses to Sam while having lunch that she can't kiss him because she wouldn't stop once she started. Lily worries that Rick isn't as interested in her now that they're married. Rick confides to Sam that he thinks the same thing about Lily. Karen and Judy go out to a bar/club. Karen isn't sure she wants to be there in the first place. She meets a man there, and feels guilty when she ends up spending the night at his place. Tad makes Jesse uncomfortable at his party. Lily tells Rick that she doesn't necessarily WANT sex, but rather just to BE with him and not have his mind a million miles away. Judy and Sam have their usual ""we can't be together but we have to

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. She cancels her dinner plans with friends and stays at home in her nightgown all day. In a moment of reflection, she wonders if she's ever been happy, or just making sure everyone else is happy. The theater janitor kicks them out, so the play rehearsal is moved to Lily's house. She even fills in for one of the students. Jesse ends up walking home from the theater. Not realizing his mom was still ho

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

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

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.

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.

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.

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.