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Christine can't afford a fancy birthday bash for Ritchie, so she hosts a homemade party to show that money isn't a factor in fun, but Ritchie ends up with a new nickname at school: poor kid.
Christine begins to wonder if her marriage could have been saved after she runs into her old counselor and suspects the woman was not really trying to help them, especially after learning that Richard had an affair with her shortly after the separation.
Christine thinks she's found a kindred spirit at Ritchie's school in a parent who shares her outlook and tastes, but the woman turns out to be Marly's maid, who uses Christine to cover for her affair with the man of the house. Belinda: Ana Ortiz.
Christine thinks she may have another chance with Burton after meeting up with him again, but he has a new girlfriend---named Christine, of course. The shock sends her into Richard's open, and apparently willing, arms.
Christine intervenes in Richard's relationship with new Christine in an attempt to reconcile them, then meets a man outside new Christine's apartment and agrees to a dinner date in the spirit of her new “say yes to life” outlook.
Christine runs into Stan again and is unable to resist him, despite her best efforts. She asks Matthew to help keep Stan away from her, but her brother is having attraction issues of his own---his latest girlfriend refuses to leave.
Christine has money problems and tries to get help from everyone except the person offering it freely: Barb. Meanwhile, Matthew gets a video message from his past and decides it's time to make something of himself.
Christine is upset that Ritchie has more fun with Richard during their weekly visits than with her every day, so she insists the guys work on a school project during their weekend together to even the “funless” factor.
At the urging of his teacher, Ritchie joins the soccer team to improve his social skills and make friends. Christine is against the idea, but Richard pushes for it until Ritchie brings home his new friends: three girls. Mr. Harris: Blair Underwood.
Richard tries to make Ritchie take an interest in his work, while Christine attempts to take an interest in her brother's life. She attends a party with him, where she runs into one of Matthew's former girlfriends and tries to help get them back together (more…)
Christine takes some sleeping pills that cause her to behave even more irrationally than usual and she ends up rekindling her romance with Burton (Matt Letscher), but finds he is only tolerable while she is on the medication.
Richard's popular brother, Joe (Charles Esten), visits with some surprising news: he is gay and wants to keep it quiet, but coming out to Christine wasn't the best choice for secrecy on the subject.
When Christine shows no interest in an election and Richard chastises her about the example that sets for Ritchie, she realizes that she needs to be more politically involved. Audrey: Sandra Bernhard. Edmund: Patrick Breen. Dot: Tara Karsian.
Christine accidentally sends an embarrassing e-mail about Mr. Harris---which was supposed to go only to Barb---to all of the parents at Ritchie's school. Christine also learns that Richard's friend Tom (Dave Foley) has a crush on her.
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