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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.
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.
Max and Caroline's attempt to break Nash into the modeling business is threatened when his mother arrives from Ireland to retrieve her son.
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.
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.
Max pursues a handsome new coworker at the restaurant, despite the owner's "no hook-up" rule.
Max and Caroline get second jobs as a pastry chef and a hostess at a trendy restaurant to help pay off their bank loan.
Max and Caroline's missing cat, Nancy, is returned by a handsome businessman; and Nancy comes home with a big surprise.
Sophie's wedding shower is disrupted by a hostage situation. The cupcake business receives bad publicity when a tenant is arrested wearing the girls' company T-shirt.
Max and Caroline learn that one of their customers at the diner is a successful photographer who is keeping a secret.
Max and Caroline get into a legal battle with two teens who knocked off their cupcake T-shirts and sold them.
Max and Caroline are arrested for breaking into a cute guy's apartment to retrieve some rings Caroline left there after she spent the night.
Caroline, Earl and Han help Oleg move into Sophie’s apartment until she starts turning his things away.
Caroline gets a shock for her birthday when she receives a Lamborghini ordered by her father four years ago. Oleg has big plans for Sophie.
Max and Caroline hire a factory to produce their cupcake T-shirts, but they become suspicious of the work conditions there due to the company's overly enthusiastic employees.
Max and Caroline obtain a bank loan to mass-produce their cupcake T-shirts so they can sell them at high-end boutiques. Meanwhile, the diner gang poses in Chestnut's barn for a holiday decorating contest Sophie entered.
Supermodels Lily Aldridge and Martha Hunt rent Max and Caroline's apartment for a fun girls' weekend.
Max and Caroline's friendship is severely tested when Caroline drags Max to a motivational business seminar to help brand their cupcake business.
Caroline takes an abandoned bicycle to start a delivery service for their cupcake business but soon discovers that Max doesn't know how to ride one.
Caroline accidentally loses one of Han's expensive fish while cleaning the tank, so Max considers selling a sentimental gift from her mother in order to replace the fish.
Max is mortified when she learns the hot guy she's been spending time with is a deejay at a grocery store.
Season 4 begins with a TV producer approaching Max and Caroline about shooting an episode of a Kardashians reality show at their cupcake window. Kim Kardashian appears as herself.