Caroline and Max walk into a hoarding nightmare and end up waist-deep in clutter when they take a job cleaning an apartment to make extra money. Plus, Max discovers Johnny has been keeping a secret from her.
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Max and Caroline try to find Chestnut a job so the horse will have lodging and shelter for the winter. Meanwhile, Peach, the mother of the twins Max babysits, auditions for television reality show Real Housewives of TriBeCa.
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When Max's stove breaks, Caroline tries to return some expensive rings to Barney's department store, but discovers her surname is no longer an asset at the store where she used to get special treatment.
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It's Valentine's Day and Max shows her softer side when Earl has a heart attack and ends up in the hospital after seeing Sophie all dressed up. Meanwhile, Caroline attempts to rekindle an old flame of hers.
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Caroline is excited to go out on her first date with Bobby, but she gets nervous when she realizes Max will be in charge of the dessert bar solo for the first time. Sophie and Oleg decide to try going out on a date instead of staying in.
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Street-wise Max and woman of substance Caroline strike up an unlikely friendship after Caroline discovers that Max can bake a mean cupcake, and the women decide if they can just wrangle up the start-up cash, they might have found their big break.
