Episodes: Series - The New Adventures of Old Christine S5 - 2010

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Because she was an illegal immigrant, Barb got caught in jail during Richard and New Christine's wedding. Christine and Matthew then go to the Bahamas to try to get her an illegal visa that will let her out of jail.

Barb and Matthew try to make things right between Richard and New Christine, but their plan doesn't work out. Along the way, Richard and Old Christine meet up with old college friends and realize how much they've changed.

Richard and New Christine agree on who will stay in their house, while Old Christine endures a severe health crisis and struggles to find quick treatment due to her lack of health insurance.

As Barb is about to marry Richard to stay in the country and avoid being deported, Christine sues Barb for alimony. Matt is asked to be Marly and Lindsay's new "therapist."

Christine is laid off from her job as a temporary secretary with Matthew, so she turns to his mentor, Dr. Max, and believes they have a romantic interest. Meanwhile, Richard and Christine's new relationship becomes more complicated, and he leaves home again.

When the most popular girl in school invites Ritchie to a dance, Old Christine thinks she's cool, but things don't go as planned. Matthew and Richard try to get an old woman to leave an apartment they want to rent.

Max confronts Old Christine about her tendency to give up on things, including relationships, when they become difficult. Therefore, he decides to be her therapist rather than her lover.

Christine sets Richard up on a date with a beautiful, emotional woman who trains out at her gym, while Richard's friend Tom keeps trying to get Christine to like him.

Barb insists on taking Old Christine on her date with Dave, fearing he might propose, while Richard is certain he has to impress New Christine to bring her back into his life.

Old Christine discovers that Ritchie is bullying other kids at school, so she decides to set a good example for him and apologize to the woman she was harassing at school, but things don't go as she wanted.

Matthew drags Old Christine to her neighbor's Christmas party, where she learns an awkward secret. Meanwhile, Richard brings Ritchie along to an unusual holiday tradition with New Christine.

Old Christine decides to tell Max that she loves him, but she is shocked by his unexpected reaction, as he refuses to be with her because he is her psychiatrist. On the other hand, Richard encourages Matthew to go on a date with their neighbor, Hannah.

Old Christine goes on a date with her old flame, Mr. Harris, after Max agrees to it, but he discovers he made the wrong decision after consulting Matthew, Barb, and Richard.

Christine is jealous when she learns that Richard and the new Christine are planning to have a child of their own. She thinks that she too should have a child.

Christine learns that the business she runs with Barb is making good money, but she can't decide whether to give her share of the money to charity or to herself. Meanwhile, Matthew finds out that Richard is hiding a secret.

Christine attempts to show Ritchie's friends how to be smart on the street and the school lets them take the subway during their field trip, but she finds herself stuck in the station after the train leaves without her.

Christine thinks Ritchie should go on a family vacation like his friends, but her intentions to take him to Florida don't work out quite the way she thought they would.

Old Christine takes New Christine, who is annoyed and very pregnant, to a fancy spa to get ready for Richard's secretly planned wedding.

When old Christine finds her life hasn't changed in five years, Max decides to help her make significant changes. After Richard returns to living with New Christine, Matthew looks for a new roommate.

Old Christine asks Matthew to stay with her to protect her from a neighborhood intruder, and New Christine goes into labor, unfortunately on Old Christine's birthday.

In order for Christine to meet Max's friends, Matthew and Barb organize her a surprise engagement party. She starts to feel less intelligent than one of the guests, which leads her to make an unexpected decision.