Once and Again - Season 3 (2005)

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 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...

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 ...

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 ...

Grace finds an "adult magazine" in their home recycling bin. 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 ...

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.

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.

Flashbacks in 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. Meanwhil,e Karen's loneliness and discomfort is compounded when Jessie cancels plans with her mother to stay at Lily's house.

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.

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.

Grace decides to join the Gay-Straight Alliance to be closer to Mr. Dimitri. Lily wonders about her daughter's sexual orientation while Jessie does not know how to face the fact that her friend Katie used to have a girlfriend.

Sam places his dream of committing to Judy and having a family squarely on the shoulders of his eleven-year-old son. Meanwhile, Jake finally realises his feelings for Tiffany and his new baby daughter.

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.

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

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

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.