Barb and Matthew visit New Christine, but only manage to get her angrier with Richard. Meanwhile, Old Christine and Richard's reunion with some old college buddies does not go as planned.
While Richard and New Christine reach a stalemate over who gets to stay in the house, Old Christine has a horrific experience as an uninsured health care patient.
Right before Barb is to marry Richard to avoid deportation, Christine sues Barb for alimony. Meanwhile, Marly and Lindsay ask Matthew to be their new "therapist."
Christine gets fired as Matthew's temporary secretary, and then develops a romantic interest in his mentor. Meanwhile, Richard and New Christine's new arrangement becomes more complicated.
Christine considers herself popular by association when Ritchie is asked to a dance by the most popular girl in school, and Matthew and Richard try to evict an elderly woman from the apartment they hope to rent.
Max points out to Christine that she quits anything that gets too hard, including relationships, which is one of the reasons he chose to be her therapist rather than her boyfriend.
Christine sets Richard up on a date with a gorgeous, passionate woman who works out at her gym, while Richard's friend, Tom, continues trying to woo Christine.
Barb asks Christine to join her on a date with Dave, and Christine insists that Richard "woo" her if he expects their rekindled relationship to survive.
Christine only makes things worse when she tries to make amends to a girl she bullied in junior high, while Matthew has a surprise in store for him when he tries to "friend" an ex-girlfriend on Facebook.
Christine and Matthew reluctantly attend a neighbor's Christmas party, while Richard and Ritchie participate in New Christine's unusual holiday tradition.
Christine goes out on a date with Mr. Harris with Max's blessing. But after consultation with Matthew, Barb, and Richard, Max finds out that he probably made the wrong decision.
Christine is torn over whether to spend her share of the gym's profits on a new dress or on charity, and Matthew discovers that Richard has an embarrassing new job.
Christine is stuck at the subway station while trying to chaperon Ritchie and his classmates on a school trip, and Barb drives through Christine's fence while responding to a naughty text.
Christine decides Ritchie deserves to go on a family vacation like his friends, but her plans to take him to Florida don't turn out quite as she had intended.
Christine impulsively demands change in her life when she discovers that her 5-year car lease is up, and Max responds with a marriage proposal. Meanwhile, Matthew seeks a new roommate after Richard moves back in with New Christine.
Matthew reluctantly agrees to stay with Christine to protect her from a prowler in the neighborhood, and New Christine does everything in her power to keep her baby from being born on Christine's birthday.
Christine feels like she is dumb after she meets Max's super-smart ex-wife at Christine's "surprise" engagement party, while Richard is forced to improvise when New Christine won't let him hold the baby.
