Since New Christine broke up with Richard, he's been spending a lot of time at Christine's house, leading Ritchie to believe that his parents are back together. When Christine tells Richard that Ritchie told this to his new teacher, Richard suggests that they give their relationship another try.
Blair Underwood ("Sex and the City", "Dirty Sexy Money", "In Treatment") guest stars as Mr. Harris, Ritchie's new teacher.
Richard tells Christine that the reason he has good luck with women is that he "says yes to life." When Christine meets a good-looking man (Scott Bakula) after paying a surprise visit to New Christine, she decides to break out of her mold and says yes when he asks her out to dinner.
Scott Bakula guest stars as the handsome stranger.
When Christine's parents can't make it to Grandparent's Day at Ritchie's school, New Christine suggests that Jeff, the new man in Christine's life, go as Ritchie's special friend. Christine learns that Jeff really is a grandfather, causing her to rethink the relationship.
Scott Bakula returns as Jeff, the new man in Christine's life.
Ritchie returns from a church festival with Richard and New Christine with a new-found interest in religion. Christine, who once had a bad experience at church, re-examines her beliefs and, with Ritchie and Matthew in tow, decides to give God another go. Ed Begley Jr. guest stars as a pastor.
Original airdate: Christine tries to be supportive of Barb during her divorce from Pete, assuming Barb will be wallowing in misery like she was after her own divorce. Meanwhile, when Barb moves in, Matthew relocates to Ritchie's room where he discovers his nephew's strange sleep habits.
When "meanie moms" Marly and Lindsay guilt Christine into serving hot lunch at Ritchie's school, she finds herself serving with Stan and vows not to sleep with him again. She and Matthew, whose date from the previous night shows no intention of ever leaving, decide they must take control of their dating lives.
Andy Richter returns as "Sad Dad" Stan.
Christine's crush on Mr. Harris makes her lose her composure around him at Ritchie's school's big fundraising gala. When Ritchie wins the coveted raffle prize of a playdate with his teacher, Mr. Harris, Christine is thrilled -- until Richard's pre-scheduled father-son plans threaten to spoil the fun.
Blair Underwood returns as Mr. Harris, Ritchie's fourth grade teacher. Mary McDonough returns as Mrs. Wilhoite, one of the parents at Ritchie's school.
When Christine receives a notice about another tuition hike at Ritchie's posh private school, she and Richard each try to figure out what they're willing to sacrifice in order to pay for their son's education. Meanwhile, Matthew realizes he hasn't been living up to his potential and considers some extreme changes. At the gym, Christine's and Barb's friendship takes an interesting new turn.
Annoyed that Ritchie finds his weekends with his dad more fun than his weekdays with her, Christine decides to make Richard responsible for having Ritchie complete his big homework assignment. But when Marly and Lindsay explain the detriment of not creating an impressive project, Christine can't help but take matters into her own hands.
When Barb starts working at Christine's women's gym, which she recently bought into, Christine can't accept the reality of not being in complete control. Meanwhile, Matthew helps Ritchie find the perfect nanny to replace him when he starts medical school.
When Christine's environmentally-friendly hybrid car and Marly's gas-guzzling monster SUV hit one another, it becomes a bigger dispute than simply who hit whom. While her car is in the shop, Christine is forced to go against her principles and rent a luxury SUV when no other car is available.
Mary McDonough returns as Mrs. Wilhoite, a mother whose child attends Ritchie's private school.
Richard feels strongly that Ritchie should join the soccer team to learn about team sports and have more male influence in his life. Christine claims not to believe in competitive sports, but finds herself in competition with Richard over Mr. Harris' attention at a soccer game.
Blair Underwood returns as Mr. Harris, Ritchie's fourth grade teacher, as well as the school soccer coach.
Christine convinces Matthew to let her go with him to his friend's party. Once there, she learns about her brother's world outside of their home, which includes some colorful friends and a pretty ex-girlfriend. Intent on being a helpful sister, she takes it upon herself to meddle in his love life. Meanwhile, Richard tries to get Ritchie interested in his job as a contractor.
Christine resents that New Christine is reaping the benefits of all the time she spent trying to perfect Richard while they were married. When New Christine gives her attentive, romantic boyfriend Richard a thoughtful birthday gift that Christine recommended, Christine can't tolerate his thinking that it was her idea.
After taking some new sleeping pills, Christine wakes up to discover she made several embarrassing phone calls while knocked out.
After sleeping with Richard's wildly attractive brother, Christine learns an astonishing secret.
Christine attempts to become politically active by volunteering to collect signatures for an environmental cause. While soliciting signatures in front of an organic grocery store, she is confronted by an activist on the opposite side of the issue (Sandra Bernhard) and the two find themselves in a bitter battle to get shoppers to sign their petitions.
Christine almost gets Mr. Harris (Blair Underwood) fired after unintentionally sending all the parents at Ritchie's school an email revealing that their parent/teacher relationship may be something more. While Christine and Mr. Harris are being reprimanded by the head of the school ethics committee, Christine gets some surprising news from Mr. Harris.
When Christine learns that Richard has been hired to remodel "meanie mom" Lindsay's bathroom, she can't help but intervene to make sure he doesn't screw up the job and risk their reputation at Ritchie's school. Additionally, she and Richard are at odds over which of them gets to be the one to give Ritchie the sex talk.
Christine's attempt to stay sober at a friend's wedding doesn't help her keep her mouth shut.
Friendships take an unexpected turn when Christine, Richard, Matthew and Barb end up in a raunchy hotel in the desert while following Ritchie to a school camping trip.
Christine realizes that one reckless evening may have jeopardized her chance to begin dating Mr. Harris, on the second season finale.