Max and Caroline try to get work for Nash as a model in an effort to make some extra money acting as his managers. Meanwhile, Sophie and Oleg attempt to remain celibate for 30 days before their wedding.
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Season 5 begins with Max and Caroline teaming up with the diner staff in a frantic attempt to keep their businesses open when the city targets Han's diner and their cupcake window for destruction.
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The girls run into Caroline's newly engaged ex, Candy Andy, and Caroline offers to make his wedding cake. Later, when she sees Andy's seemingly perfect relationship, she wonders if she should have stayed with him.
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Han believes his diner employees are not working together as a team, so he insists they all attend a mandatory night out at the Escape Room club.
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Max is puzzled and curious when her new beau expresses hesitations about intimacy because he is "not regular down there." Meanwhile, Sophie and Oleg struggle to get pregnant.
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Max & Caroline interfere with a basketball game in an attempt to promote their cupcakes, but the chaos that ensues threatens to ruin their business' reputation.
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Earl is crushed when he is not invited to play with his old jazz band at their reunion show, so the diner gang join forces to help get Earl back performing on stage.
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Max and Caroline sign up for Booth Babes in order to get into a large gaming convention for free. Once inside, they discover Han's friend created video game characters based on them so they demand compensation.
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Caroline shares her riches-to-rags life story on stage at a storytelling night and captures the attention of a Hollywood studio executive. Meanwhile, Sophie and Oleg search for a surrogate.
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Max tags along with Caroline as she travels to Los Angeles on a film studio's dime to discuss the idea of making her riches-to-rags life story into a movie. While there, Max loses her luggage but finds a new crush.
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