New Adventures of Old Christine

Season 5 opens shortly after Richard was left at the altar. As Richard plans to win New Christine back, Christine and Matthew disparage their lost loves. However, when Christine finds out Barb is being detained and may be deported, she runs to her side. Barb thinks a guy named Bongo can help her, so Christine and Matthew fly to the Bahamas to find him. Unfortunately, Christine loses her passport and ends up being detained in the Bahamas; they return 24 hours later with no Bongo. Meanwhile, Richard finds out New Christine is over him and is moving on. And Barb’s immigration officer flirts with her saying if she’s in a sham marriage, he’ll overlook it and reinstate her status. Barb and Richard announce their engagement.

Christine decides to plan a get together with all their old friends (guest stars Jeanette O’Connor, Wayne Nickel, Dave Florek) from college in order to cheer up Richard, who’s still depressed about the breakup with New Christine. When they arrive, all their old friends are much older than expected and Christine is horrified by the thought they’re old too. Meanwhile Barb and Matthew go to New Christine’s to pick up some clothes for Richard. Matthew doesn’t think New Christine’s blasé attitude is healthy and pushes her to connect with her anger. She ends up burning Richard’s clothes. When they tell Richard about New Christine’s rage, he is delighted: her previous apathy upset him, but anger is a cousin of love and he knows there’s still hope for them.

Christine panics when she discovers a suspicious mole and can’t find a doctor to treat her because she has no health insurance (it lapsed when they left The Bloom Corporation). She becomes vaguely political and decides to make a documentary blowing the lid off the health care crisis. Her newly found passion quickly diminishes when a friend of Matthew’s from medical school examines her and it turns out the mole is a piece of brownie. Meanwhile Richard and New Christine fight over what to do about their house and finally decide they can live together amicably, but not romantically.

Christine gets a lawyer (guest star Corbin Bernsen) after she learns Barb got one to handle their divorce. Unfortunately, Christine’s divorce lawyer is very aggressive and persuades Christine to ask for money. This leads to a breakdown in their friendship, but they end up reconciling in time for Christine to be the maid of honor at Barb and Richard’s wedding. Also, the meanie moms offer Matthew a lot of money for therapy but it turns out they don’t really want therapy, they just want Matthew to compliment them.

With the gym closed for repairs, Christine decides to be Matthew’s secretary after his quits. Turns out she’s a great secretary, except she starts convincing his patients they are okay and don’t need to come in. They end up having a huge fight, and she turns to Matthew’s suite-mate and mentor, Max Kershaw (special guest star Eric McCormack), for support. She thinks she’s dating Max, but he thinks she’s coming for therapy and they never quite get their signals straight. Richard and New Christine, now living together platonically, end up having sex (she’s a very sexual person). Unfortunately Richard thinks they’re back together and to New Christine, it was just sex. Richard decides he has to move out.

Christine is thrilled when Britney B (guest star Stefanie Scott), the most popular girl in school, asks Ritchie to the 7th grade dance. She thinks they’ve become popular and isn’t shy about lording it over the meanie moms (guest star Mary Beth McDonough). But when Christine learns that she wants to break up with him at the dance, she pays Britney $100 to stay with him, a process that quickly diminishes her popularity. Also, Richard and Matthew must convince a woman (guest star Marion Ross) to leave her apartment in order for them to move into it, and eventually do so by moving her into Christine’s place.

When Christine learns that Barb had Matthew do a backup recommendation for her INS application, she seeks solace with her new therapist, Dr. Max Kershaw. Unfortunately, Max confronts her with the issue that she does bail on things when they get hard. He puts her through the ropes to encourage her to finish things and when she finally has a mini-breakthrough, the end up hugging, reinforcing, once again that they are attracted to each other. Also, Matthew and Richard have moved in to their new apartment, but Richard doesn’t love the new arrangement: Matthew has set all these boundaries because of his lack of boundaries in his former arrangement with Christine and is no fun to live with.

Christine and Richard set each other up on blind dates: Richard is thrilled with Christine’s choice and ends up having endless sex with her, however when he tries to break up with Tracey (special guest star Jennifer Grey) because he is still in love with New Christine, she gets stalker crazy on him; Christine is furious because Richard sets her up with Tom again, but even though she’s not interested she decides to accept his offer to take care of her. New Christine arrives at Christine’s place and drops a bombshell on Richard.

Barb insists that Christine join her on a date with Dave, the INS officer she’s been dating since she got detained for problems with her immigration status. Barb is afraid Dave (guest star James Lesure) is going to propose and she doesn’t want to get married; she likes things the way they are and if he proposes, she’s going to have to break up with him. When Dave and Christine are alone, he reveals that he wants to break up with her. Christine convinces him to let Barb down gently and that he should propose to her so she’ll break up with him. When he proposes, she accepts, much to his chagrin. Christine tells him that Barb will eventually break-up with him. 10 years later, Dave tells his and Barb’s kids how he met their mother. Richard learns that just because New Christine is pregnant, they’re not automatically back together. Richard must woo New Christine in order to win her back.

In order to set a good example for Ritchie, who has been caught bullying at school, Christine locates and apologizes to Frances Stein (guest star Amy Sedaris), the girl she bullied when she was in 7th grade. Frances tells Christine that she was traumatized by the teasing and only years of therapy and plastic surgery have helped her recover. She refuses to accept Christine’s apology. Upset that she wasn’t able to right her past wrongs, Christine asks Barb to put in a good word for her. Unfortunately, Frances thinks Barb is threatening her and when Frances goes to the gym to let Christine know she accepts her apology, things go from bad to worse as Christine ends up tying her up to get her to calm down.

Christine gets cajoled into going to the neighborhood Christmas block party by Lucy, Matthew’s old girlfriend that he’s started dating again. It’s a great party and Christine fits in well, but when she sees her neighbor’s husband kissing another woman, she’s confused. She tells her new friend who gets mad at her for being so "judgy", turns out the neighborhood is filled with swingers. Richard and New Christine introduce Ritchie to New Christine’s crazy family Christmas celebration called Kinderclausen. It’s got lots of weird traditions, like only new babies get store-bought presents. Ritchie doesn’t like it, so to appease him, New Christine mentions another Kinderclausen tradition where the oldest child gets to name the new baby. Ritchie decides to name the new baby Xbox 360, because that’s what he really wants. Also, Matthew and Lucy, only recently reunited, break up again because of Lucy’s sense of reality: Matthew can’t deal with the fact she truly believes in Santa Claus.

Christine tells her therapist, Max, that she is in love with him, but his reaction is not what she was expecting. Richard encourages Matthew to go out with their neighbor, Hannah, but the date ends up uncomfortable for Matthew after she saw his "Mong", which is a male thong that Max’s sister created. Christine also sees Max wearing the "mong" after he helps her with a flat tire, where he confesses that he actually loves her but they can’t date since he’s her psychiatrist. She fires him, and they make out in her car.

Christine and Max have been dating for three weeks when at dinner she lets out that she loves him. Max does not say it back and when she receives a text message from an old boyfriend, Mr. Harris (guest star Blair Underwood), he even dares her to go out with him saying they have not said they are exclusive yet. Christine takes the dare and sets up a date with Mr. Harris who everyone, especially Matthew, thinks is gorgeous. As soon as Christine leaves for the date, Max shows up at Christine’s house and admits to Matthew that he really does love Christine but wanted to give her "space" since he has ruined many relationships before because he latched on too fast. Matthew, Richard and Barb take Max to find Christine. Meanwhile, Christine is on her date with the stunning Mr. Harris but all she can talk about is Max. Mr. Harris admits he only asked Christine on this date to make his ex-girlfriend jealous and both of them work to forget their significant others but realize they no longer have any spark between them, when Max suddenly shows up and confesses that he loves her.

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.

When Christine and Barb find their business unexpectedly profitable, Christine undergoes a personal crisis - deciding whether to spend her share of the new-found money on herself. Matthew suspects something when Richard begins to lie to New Christine about where he is.

In an effort to teach Ritchie’s class some street smarts, Christine encourages the school to let them take the subway on a field trip but 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.

After a good-looking cop, who Old Christine assumes is a stripper, alerts her that there is a prowler in the neighborhood, she convinces Matthew to stay over. Meanwhile, New Christine goes into labor - on Old Christine’s birthday.

Series finale. 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.