Bahamian Rhapsody
Series 5, Episode 1 Unrated
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Christine's 13-year-old son, Ritchie (series star TREVOR GAGNON), is now starting middle school at the posh private school where Christine endures endless encounters with two snooty, stay-at-home "meanie moms," Marly (series star TRICIA O'KELLEY), and Lindsay, (series star ALEX KAPP HORNER). Keeping Christine grounded is her younger brother, Matthew (series star HAMISH LINKLATER), who lives with her, helping to care for Ritchie and serving as her emotional rock. The formerly floundering Matthew recently found his path, and it wasn't with the help of a therapist; in fact, it's as a therapist. Everyone seems to be making changes with their lives; now Christine is trying to do the same with hers.
In the fifth season premiere, Christine and Matthew fly to the Bahamas to help get Barb an illegal visa, after she was thrown in jail by immigration during Richard and New Christine's disastrous wedding in the season four finale.
Burning Love
Series 5, Episode 2 Unrated
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Christine and Richard meet up with some old college buddies and are shocked to see how much their friends have aged.
The Mole
Series 5, Episode 3 Unrated
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Christine thinks she is dying after Richard awkwardly spots an irregular mole on her chest, and panics when she can't get in to see a doctor fast enough. Meanwhile, Richard decides he needs to move back in with New Christine.
For Love or Money
Series 5, Episode 4 Unrated
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After Barb has her lawyer send over divorce papers, Christine hires an aggressive divorce attorney, Howard (guest star CORBIN BERSEN - Pysch, L.A. Law), who convinces her that Barb owes her alimony.
Doctor Little Man
Series 5, Episode 5 Unrated
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Christine begins seeing a therapist, Dr. Max Kershaw (recurring guest star ERIC McCORMACK - "Will & Grace"), who shares office space with Matthew, although it's unclear whether Christine is interested in pursuing therapy or romance.
The Curious Case of Britney B
Series 5, Episode 6 Unrated
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Christine surpasses the Meanie Moms in popularity when Ritchie is asked to a dance by the most popular girl in school. Plus, Matthew and Richard try to evict an elderly woman, Agnes Ross (guest star MARION ROSS - Happy Days), from the apartment they hope to rent.
Nuts
Series 5, Episode 7 Unrated
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Max (recurring guest star ERIC McCORMACK) points out to Christine that she tends to quit things when they get too difficult, including relationships. This, he says, is one of the reasons he chose to be her therapist rather than her boyfriend.
Love Means Never Having to Say You're Crazy
Series 5, Episode 8 Unrated
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Christine sets Richard up on a date with Tracey (guest star and real-life wife of series star Clark Gregg, JENNIFER GREY - Dirty Dancing), a gorgeous, passionate woman who works out at her gym. Meanwhile Richard's friend, Tom (recurring guest star DAVE FOLEY - News Radio), who has a longstanding crush on Christine, continues trying to woo her.
I Love Woo, I Hate You
Series 5, Episode 9 Unrated
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Barb insists that Christine join her on a date with Dave (recurring guest star JAMES LESURE - For Your Love, Las Vegas), the immigration officer Barb has been dating, fearing that he might propose to her. Meanwhile, Richard realizes he must woo New Christine in order to get her back.
Old Christine Meets Young Frankenstein
Series 5, Episode 10 Unrated
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When Christine finds out that Ritchie has been bullying other kids, she decides to set a good example and apologize to the woman she used to terrorize at school when she was young. Guest star AMY SEDARIS (Strangers with Candy) appears as Frances, the woman Christine dubbed "Frankenstein" in junior high school, and MICHAELA WATKINS (Saturday Night Live) returns as Matthew's unstable girlfriend, Lucy.
It's Beginning to Stink a Lot like Christmas
Series 5, Episode 11 Unrated
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Christine reluctantly attends her neighbor's holiday block party where she discovers a juicy secret. Guest star MOLLY SHANNON (Saturday Night Live, Evan Almighty) appears as Christine's neighbor, Jeannie, and recurring guest star MICHAELA WATKINS appears as Matthew's girlfriend, Lucy.
A Whale of a Tale
Series 5, Episode 12 Unrated
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When Christine decides to tell her therapist she's in love with him, his response is not what she expected. Recurring guest star ERIC McCORMACK appears as Max, Christine's therapist.
Truth or Dare
Series 5, Episode 13 Unrated
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Christine finds herself falling in love with Max (recurring guest star ERIC McCORMACK) until her ex-boyfriend, Mr. Harris (recurring guest star BLAIR UNDERWOOD), comes back into her life. Will she have to choose?
A Family Unfair
Series 5, Episode 14 Unrated
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Christine feels left out as Richard and New Christine plan for their baby and decides she wants one too and decides to ask Richard for his help. Guest star TIM MEADOWS (Saturday Night Live, The Bill Engvall Show, Walk Hard: The Dewey Cox Story) appears as Dr. Volk, New Christine's OB/GYN.
Sweet Charity
Series 5, Episode 15 Unrated
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When Christine and Barb find their business unexpectedly profitable, Christine undergoes a personal crisis trying to decide whether to spend her share of the newfound money on herself and splurge on a designer dress, or to follow Barb's lead and give it to charity. Guest star ED BEGLEY JR. (Gary Unmarried, Arrested Development, Pineapple Express, St. Elsewhere) appears as Pastor Ed.
Subway, Somehow
Series 5, Episode 16 Unrated
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Christine urges Ritchie's school principal (recurring guest star NANCY LENEHAN - My Name Is Earl, Worst Week) to let the class take the subway on a field trip in order to learn real-world skills. But when the train leaves without her, Christine finds herself stranded at the station.
Up in the Airport
Series 5, Episode 17 Unrated
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When Christine realizes Ritchie's never been on a real family vacation like his classmates, she plans a trip to Florida. But things don't turn out quite as she intended and the trip goes horribly awry.
Revenge Makeover
Series 5, Episode 18 Unrated
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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. Recurring guest star SCOTT BAKULA appears as Old Christine's ex-boyfriend and New Christine's father, Papa Jeff.
I Love What You Do for Me
Series 5, Episode 19 Unrated
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When Christine discovers that her five-year car lease is up, she evaluates her life during that time and realizes that not much has changed. She vows to make some big changes. Max (recurring guest star ERIC McCORMACK) offers to help.
Scream
Series 5, Episode 20 Unrated
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Christine convinces Matthew to stay over after a good-looking cop named Officer Johnson (guest star JOSH RANDALL – Ed), who Christine assumes is a stripper, alerts her that there is a prowler in the neighborhood. Meanwhile, New Christine goes into labor — on Old Christine's birthday. Recurring guest star Tim Meadows appears as Dr. Volk, New Christine's OB/GYN.
Get Smarter
Series 5, Episode 21 Unrated
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In the fifth season finale, Christine has Matthew and Barb throw her a "surprise" engagement party so she can get to know Max's (recurring guest star ERIC McCORMACK) friends. But she begins to feel intellectually inferior to one particular guest, driving her to make a "surprising" decision.
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