S1E1 - Pilot
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.
Sept. 21, 1999, midnight
S1E2 - Let's Spend The Night Together
Rick and Lily ponder taking their relationship to the next level.
Sept. 28, 1999, midnight
S1E3 - The Scarlet Letter Jacket
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.
Oct. 5, 1999, midnight
S1E4 - Liars and Other Strangers
After meeting Rick, Judy expresses to Lily her misgivings about Lily's blossoming relationship with him.
Oct. 12, 1999, midnight
S1E5 - There Be Dragons
Rick introduces Lily to his kids under awkward circumstances.
Oct. 19, 1999, midnight
S1E6 - A Dream Deferred
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.
Oct. 26, 1999, midnight
S1E7 - The Ex-Files
Being divorced means Karen and Rick must both go to Eli's weekend basketball tournament, creating some awkward moments for them.
Nov. 2, 1999, midnight
S1E8 - The Past is Prologue
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.
Nov. 9, 1999, midnight
S1E9 - Outside Hearts
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.
Nov. 16, 1999, midnight
S1E10 - Thanksgiving
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.
Nov. 23, 1999, midnight
S1E11 - Where There's Smoke
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.
Dec. 7, 1999, midnight
9.0
S1E12 - The Gingerbread House
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.
Dec. 21, 1999, midnight
S1E13 - Mediation
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.
Jan. 24, 2000, midnight
S1E14 - Sneaky Feelings
Eli feels tempted to cheat on Jennifer. Karen feels attracted to a younger co-worker.
Jan. 31, 2000, midnight
S1E15 - The Mystery Dance
Rick and Lily begin to mend their relationship. Judy meets a man who might fulfill her dreams.
Feb. 7, 2000, midnight
S1E16 - Daddy's Girl
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.
Feb. 14, 2000, midnight
S1E17 - Unfinished Business
Lily and her family cope with a life-altering accident.
March 6, 2000, midnight
S1E18 - Strangers and Brothers
Aaron proves to be a source of comfort and renewal for the Manning family; Lily gains ground in the divorce proceedings.
March 13, 2000, midnight
S1E19 - Cat-In-Hat
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.
April 3, 2000, midnight
S1E20 - My Brilliant Career
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.
April 10, 2000, midnight
S1E21 - Letting Go
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.
April 17, 2000, midnight
S1E22 - A Door, About to Open
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
April 24, 2000, midnight