Sophie's wedding is interrupted by a hostage situation. Meanwhile, Max and Caroline's cupcake business gets some unwanted attention when a tenant who is wearing one of their company's T-shirts is arrested.
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Sophie takes Max and Caroline shopping for their bridesmaid dresses, so the girls enlist the diner gang's help to hide the most hideous ones to avoid being utterly humiliated.
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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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Max and Caroline help launch the opening of The High's new location at JFK airport. Meanwhile, Sophie learns that Oleg may have an ulterior motive for wanting to marry her.
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Season 4 ends with Max and Caroline tasked with retrieving Sophie's wedding dress from airport customs and safely transporting it to the church in time for the nuptials.
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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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Caroline's grandmother Astrid awakens from a coma with no knowledge of her family's massive money scandal, so Caroline tries to keep the truth from her a bit longer by giving Astrid one last fancy luncheon.
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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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