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.
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.
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.
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.
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.
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!