Lily tells Jake she wants a divorce, and tells Rick about her one-night stand with Jake. Rick can't forgive her, putting their future in jeopardy.

Lily Manning, separated from her husband, and Rick Sammler, divorced for 3 years, meet by chance when her daughter, Grace, injures her ankle in a soccer game. They go out on a date, and are instantly attracted to each other.

Rick and Lily ponder taking their relationship to the next level.

Rick and Lily's families gather at the school carnival. Lily and Karen, who don't know of each other at this point, are paired to work together in a booth there.

After meeting Rick, Judy expresses to Lily her misgivings about Lily's blossoming relationship with him.

Rick introduces Lily to his kids under awkward circumstances.

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.

Being divorced means Karen and Rick must both go to Eli's weekend basketball tournament, creating some awkward moments for them.

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.

While Lily is at a convention, Judy allows Grace (and Rick and Karen allow Eli), to go to a party that ends up with bad consequences.

Lily's father decides to invite Jake to Thanksgiving at Lily's house against her wishes. Her father has difficulty in deciding whose side of the divorce to support.

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.

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.

Eli feels tempted to cheat on Jennifer. Karen feels attracted to a younger co-worker.

Rick and Lily begin to mend their relationship. Judy meets a man who might fulfill her dreams.

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 and her family cope with a life-altering accident.

Aaron proves to be a source of comfort and renewal for the Manning family; Lily gains ground in the divorce proceedings.

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.

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.

When Judy's continuing affair with Sam is discovered, she takes steps to prevent any more pain from entering her life. Lily realizes just how much she's taken Rick for granted when he's sick in the hospital. Grace continues to have difficulty with accepting her father's past infidelity.

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

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.

Parental pressure bears down on Eli to get his act together for college. However, Eli wants to form a music group.