Season 6 ends with the girls and the diner gang preparing for their big night on the red carpet, as the premiere of the film about Caroline's life arrives. Meanwhile, Max and Caroline contemplate their future at the diner and the states of their love lives.
The girls are excited when they are invited to a press junket to promote the film about Caroline's life, but Caroline gets a surprise when her ex-boyfriend, Candy Andy, shows up. Meanwhile, Bobby gets jealous over Caroline and Candy Andy's reconnection and asks the diner gang for advice.
Caroline tries to embrace Bobby's hobby of bowling, but she fears she is his bad luck charm when she accidentally injures his teammate's hand, which threatens their chance for a championship. Meanwhile, Max uses her bowling prowess to get onto Bobby's team; and Sophie worries that baby Barbara might not be smart enough.
Caroline and Bobby head toward their first fight when she encourages his sister to quit her job at the company run by her mother. Meanwhile, Max reads a text on Bobby's phone that suggests he has a child with his ex, Jessica, so she and Han go undercover as an engaged couple to Jessica's wedding planning shop to find out the truth.
Han's new therapist suggests that Max needs to confront her "daddy issues" and fear of intimacy, so she reluctantly heads to Rhode Island to track down her birth father with the diner gang in tow. Meanwhile, Oleg gets upset when Sophie asks him to help out around the house.
Caroline tries to make a good impression when she meets Bobby's family at a party, but she isn't prepared when his mother and sisters keep comparing her to his ex-girlfriend. Making things worse, the diner gang decides to tag along.
Caroline prepares for her third date with Bobby and tries to spice things up by taking a burlesque class. She's accompanied by a reluctant Max, who decides to give up sex in the wake of her breakup with Randy. She also goes golfing with Han.
Caroline is excited to go out on her first date with Bobby, but she gets nervous jitters when she realizes Max will be in charge of the dessert bar solo for the first time. Meanwhile, Sophie and Oleg decide to mix things up and try going out on a date instead of staying in.
Max and Caroline return from their road trip, and Caroline is impressed with not only the dessert bar renovations but also with the contractor on the job. Meanwhile, Max rushes to see Randy when she learns he is in a New York City hospital; and Sophie joins a mommy group that cares less about baby talk and more about partying.
Max and Caroline are cast as zombie extras when they arrive on the movie set in Texas where Randy is working. Back at home, Han and Oleg try their hand at construction after they fire the contractor working on the dessert bar.
Max decides to head to Los Angeles to win back Randy, so she and Caroline embark on a cross-country road trip with Han at the wheel. Back in New York, Oleg takes charge of the diner and Sophie fills in as a waitress.
When a hurricane approaches, Caroline fears a big divorce party she's planning for a wealthy couple will get canned when the unhappy pair get stranded in close quarters at the dessert bar. Meanwhile, Max worries that Randy really did break up with her when she suspects he is blocking her calls; and Oleg gets jealous when Sophie is stuck at home during the storm with their handsome new "manny."
Randy and Max tire of Caroline being the third wheel on their FaceTime dates, so Randy sets her up on a date with one of his co-workers. Meanwhile, Oleg becomes distraught when Sophie tells him to sell his beloved car for a minivan.
Max and Caroline's dessert bar business booms when they hire a popular bartender, but the girls are forced to intervene when Han becomes addicted to the mixologist's potent cocoa powder in his signature cacao drink. Meanwhile, Han enters a duck stamp drawing contest; and glamour eludes Sophie as she adjusts to being a mom.
The girls take a bartending class in order to add cocktails to their dessert bar menu, but Caroline is forced to take the class exam alone when Max gets chicken pox from Han. Meanwhile, Sophie introduces a creepy lookalike video monitor doll to keep tabs on baby Barbara, which unsettles everyone.
Earl becomes concerned he may not be able to keep up when his long-lost sweetheart, Pilar, visits from Cuba and wants him to take her sightseeing around the country. Meanwhile, Max must decide whether it's time to take her texting relationship with Randy to the next level.
Max gives Caroline the college party experience she never had when they are invited to speak at Caroline's alma mater, the University of Pennsylvania, about their business. Meanwhile, Oleg's attempts to bond with baby Barbara are rebuffed by a possessive Sophie; and Han practices his magic tricks with a reluctant Earl as his assistant.
Oleg and Sophie's plan to have Max and Caroline as Barbara's godparents goes awry when Oleg's domineering mother arrives from the Ukraine for the baby's baptism and fires the girls from their godparent duties.
Max and Caroline's plans to attract upscale clients to their dessert bar go awry when members of an arm-wrestling team become regulars. Meanwhile, Oleg ghost writes sexy messages for Max to send to Randy.
Sophie goes into labor just before the Dessert Bar's grand opening and demands that Max and Caroline be present for the birth. Meanwhile, the girls run into problems when they don't secure a liquor license for their new venue.