Christine and Matthew fly to the Bahamas to get Barb an illegal visa after she was arrested by immigration during Richard and New Christine's wedding ceremony.
When Christine and Richard meet up with some of their friends from college, they are shocked to see how much they've aged.
Richard discovers a suspicious mole on Christine's chest, and she panics when she can't immediately see a doctor. Meanwhile, Richard decides that it would be best if he moved back in with New Christine, but he has to engage her in a battle of wills if he's to make it happen.
When Barb sends over divorce papers, Christine hires an aggressive divorce lawyer who demands that Christine gets alimony.
Christine starts seeing a therapist who shares office space with Matthew, but they are both confused on whether they want to have a professional or romantic relationship.
When Ritchie is asked to a dance by the most popular girl in school, Christine believes that she is popular by association and has finally surpassed the Meanie Moms. Meanwhile, Matthew and Richard find an apartment that they want to rent together. Unfortunately, they will have to find a way to evict an old lady that lives there before they can move in.
Max tells Christine that she quits things at the tiniest obstacle and tries to get her to stick to what she's started.
Tom returns and makes another attempt to woo Christine, and Christine sets Richard up with a beautiful and passionate woman that works out at her gym.
Christine convinces Lindsay that being single is the key to happiness, which prompts her to leave her husband and move in with Christine.
Christine notices that Ritchie has been bullying other kids, and she decides to show a good example by apologizing to the woman she used to bully.
While reluctantly attending her neighbor's block party, Christine uncovers a juicy secret.
The response of her therapist is not quite what she had expected after Christine tells him that she's in love with him.
Right before Mr. Harris comes back into her life, Christine finds herself in love with Max.
Christine asks Richard for his help in order for her to have a new baby when she finds out Richard and New Christine plan on having their own baby soon.
After the business she shares with Barb turns out to be profitable, Christine is put between a rock and a hard place deciding whether to spend her share of the money on herself or on charity.
While attempting to teach some street smarts to Ritchie's class, Christine's suggestion of the school taking the students on a field trip ends in disaster when she ends up stranded at the station as the train leaves without her.
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.
Old Christine takes a cranky, very pregnant New Christine to a fancy salon to prepare her for the impromptu wedding that Richard is secretly planning.
When Christine is told that her five-year car lease is up, she realizes that her life hasn't evolved during that time the way she'd hoped and decides to make some major life changes, with a little help from her boyfriend, Max. Meanwhile, Matthew seeks a roommate to replace Richard.
Christine mistakes a good looking cop for a stripper, who alerts her that there is a prowler in the neighborhood. In order to feel more secure, Christine asks Matthew to stay over. Later on, New Christine goes into labor; unfortunately for Old Christine, it happens to take place on her birthday!
Christine has Matthew and Barb throw her a "surprise" engagement party so she can meet Max's friends, but she feels intellectually inferior to one guest in particular, and it leads her to make a surprising decision.