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.

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

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

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 pursues her teacher and Jessie develops an attraction for her friend Katie.

The prospect that Grace may be romantically involved with her creative-writing teacher troubles Lily, infuriates Jake, and imperils the career of the instructor.