After Barb wound up in jail during Richard's and New Christine's wedding due to her immigration status, Christine and Matthew head to the Bahamas in order to try to get an illegal visa to get her out of jail.
Christine and Richard must face the shocking reality of how much they have aged when they run into some old college friends.
After Christine finds a weird mole, she panics, but can't get to a doctor fast enough, while Richard makes the decision that he wants to move back to New Christine.
An aggressive divorce attorney is hired by Christine after being convinced that Barb owes her alimony.
Christine's relationship with the doctor becomes complicated when he shares an office space with Matthew.
Ritchie is asked to a dance by the most popular girl in school. Elsewhere, Richard and Matthew have their sights set on an apartment they want to rent but must first force out it's elderly tenant.
Max decides it's time to tell Christine that she quits anything that gets too hard for her, which includes relationships, and he points out that is the reason he chose to be her therapist rather than her boyfriend.
Christine has set up a date between Richard and a gorgeous, passionate woman who works out at her gym, while Tom (Richard's friend) continues trying to woo Chrisine.
After Christine convinces Lindsay that single life is the way to go, Lindsay leaves her husband and moves in with her, making Christine her divorce role model.
Christine is informed that Ritchie has been bullying another kid. She is guilt-tripped into trying to set 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.
Max offers to help Christine make a major life change after she realizes that her five-year car lease is up and her life hasn't evolved in all that time
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!
When Christine has Matthew and Barb throw her a "surprise" engagement party so she can get to know Max's friends, she begins to feel intellectually inferior to one particular guest, driving her to make a "surprising" decision