Divorced working mother Christine Campbell (series star Julia Louis-Dreyfus) owns a women's 30-minute workout gym, successfully juggling the daily stresses of motherhood and her business. Her 8-year-old son, Ritchie (series star Trevor Gagnon), has just been accepted into a posh private school frequented by two snooty stay-at-home moms, Marly (series star Tricia O'Kelley) and Lindsay (series star Alex Kapp Horner). Christine's twenty-something slacker brother, Matthew (series star Hamish Linklater), lives with her and also serves as Ritchie's babysitter. Christine gets along with her charming ex-husband, Richard (series star Clark Gregg), even better than when they were married, but her life gets a lot more complicated when she meets Richard's new girlfriend: a nice, young, impossible-to-hate woman also named Christine (series star Emily Rutherfurd)...the "new" Christine.

Upon learning that Richard and "new" Christine are enjoying an intimate relationship, Christine becomes determined to make her own romantic conquests. After several failed attempts to meet eligible men, she finally runs into a divorced guy named Stan (recurring guest star Andy Richter - "Andy Richter Controls the Universe") at the grocery store. Unbeknownst to Christine, however, needy Stan is known as "Sad Dad" at Ritchie's school.

Upon learning that her close friend Barb (recurring guest star Emmy Award winner Wanda Sykes - "The Chris Rock Show") is responsible for matching up "new" Christine and Richard, Christine allows Barb to set her up on a blind date of her own. After a series of unsuccessful dates, Christine finds the possibility of love in the strangest of places. Meanwhile, Matthew takes Ritchie to swimming lessons.

Upon learning from the gloating Matthew that Christine is out enjoying her fifth date with an attorney, Burton (recurring guest star Matt Letscher - "Joey"), Richard does what any self-respecting ex-husband would do: He sabotages the happy couple's goodnight kiss and insults Burton with lawyer jokes. But when Richard tries to make it up to the pair by inviting them to dinner with him and "new" Christine, his best-laid plans go awry.

Christine gets nervous when Burton (recurring guest star Matt Letscher) tries to take their relationship to the next level. After 10 dates, Christine faces a critical moment. Will she or won't she--let him in the house, that is, to meet her son, Ritchie. She eventually relents, only to freak out even more later.

Concerned about the uniformity of Ritchie's schoolmates, Christine takes it upon herself to help diversify the student body at his exclusive private school. But her attempt to promote racial and ethnic diversity has unintended consequences. Recurring guest star Wanda Sykes appears as Christine's friend Barb.