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.

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.

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.

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

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