Sophie and Oleg welcome their baby daughter Barbara to the world. Randy returns to briefly continue his relationship with Max, but it does not work out. Randy wants Max to move to California, but Max, publicly acknowledging her strong friendship with Caroline for the first time, says she cannot do so because she has important people in her life now. Meanwhile, Caroline meets Bobby, a contractor who rebuilds the dessert bar after a storm, and the two start a relationship. By the end of the season, the movie about Caroline's life has been made (albeit with some "creative license" changes), but Caroline destroys a $10,000 on-loan dress at the premiere, which wipes out both her and Max's combined savings and returns them to "broke" status. Randy comes back to New York, this time permanently, and proposes to Max, who accepts
As Max and Caroline, now part owners of the diner, put the finishing touches on their newly converted Dessert Bar, Max deals with the aftermath of her recent breakup with Randy, and Sophie and Oleg prepare for the birth of their baby.
Max and Caroline’s plans to attract a more sophisticated clientele to their dessert bar take a turn when Max befriends a bouncer whose team of arm wrestlers becomes their latest patrons. Also, Max and Randy continue to text each other, but when she runs out of sexy messages to send him, Oleg offers to be her ghost writer.
Oleg and Sophie’s plan to have Max and Caroline as Barbara’s godparents is derailed when Oleg’s domineering mother, Olga, arrives from the Ukraine for the baby’s baptism and fires Max and Caroline from their godparent duties.
When Caroline and Max are invited to speak about their business at Caroline’s alma mater, the University of Pennsylvania, Max takes the opportunity to give Caroline the college partying experience she never had. Also, 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.
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. Also, Max must decide whether it’s time to take her texting relationship with Randy to the next level.
When the girls take a bartending class in order to add cocktails to their dessert bar menu, Caroline must think quickly when she has to take the class exam solo after Max gets chicken pox from Han. Also, Sophie creates a creepy lookalike video monitor doll to keep tabs on baby Barbara.
Max and Caroline's dessert bar business booms when they hire Clint, a popular bartender, but the girls need to intervene when Han becomes addicted to the mixologist's potent cocoa powder in his signature cacao drink. Also, Han enters a duck stamp-drawing contest, and glamour eludes Sophie as she adjusts to being a mom.
When Randy and Max get tired of Caroline being the third wheel on their FaceTime dates, Randy sets her up with one of his co-workers. Also, Oleg is distraught when Sophie tells him to trade in his beloved car for a minivan.
When a hurricane approaches the area, Caroline fears that a big divorce party she's planning for a wealthy couple will get broken up when the unhappy pair get stranded in close quarters at the dessert bar. Also, Max worries that Randy really did break up with her when she suspects he’s blocking her calls, and Oleg is jealous when Sophie is stuck at home during the storm with their handsome new "manny".
When Max decides to head to Los Angeles to win back Randy, she and Caroline embark on a cross-country road trip with Han at the wheel. Also, while Han and the girls are away, Oleg takes charge of the diner, and Sophie fills in as a waitress.
As Max and Caroline's road trip misadventures continue, their lack of money finds them stowing away and waitressing on a riverboat to New Orleans as Max tries to reach Randy in Texas. Back at the diner, Oleg and Sophie rake in big bucks when they sell pony rides with Chestnut.
Max and Caroline get their big break when they’re cast as zombie extras after they finally arrive at 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.
When Max and Caroline get home from their road trip, Caroline discovers she likes the dessert bar renovations as much as she likes Bobby, the contractor on the job. Also, Max rushes to Randy’s side when she hears he’s in the hospital in New York City, and Sophie joins a mommy group that cares more about partying than baby talk.
Caroline is excited to go out on her first date with Bobby, but she has nervous jitters when she realizes Max will be alone and in charge of the dessert bar for the first time. Also, Sophie and Oleg decide to mix things up and go out on a date instead of staying in.
As Caroline prepares for her third date with Bobby, she decides to spice things up by taking a burlesque class accompanied by a reluctant Max, who decides to give up sex in the wake of her breakup with Randy. Also, Max decides to take up a new hobby and goes golfing with Han.
When Bobby invites Caroline to a party to meet his family, she is eager to make a good impression but isn’t prepared for the torch that his mother and sisters still carry for Bobby’s ex-girlfriend. Also, Caroline’s nerves are even more frayed when the diner gang decides to tag along.
When Han's new therapist suggests that Max needs to confront her "daddy issues" and fear of intimacy, she reluctantly heads to Rhode Island to track down her birth father with the diner gang in tow. Also, Oleg is up in arms when Sophie wants him to help out around the house.
When Caroline encourages Bobby’s sister, Denise, to quit her job, the couple heads toward their first fight after Caroline realizes the company Denise works for is her mother’s. Also, after Max reads a text on Bobby’s phone suggesting he has a child with his ex, Jessica, she and Han go undercover as an engaged couple to Jessica’s wedding planning shop to find out the truth.
Caroline makes an effort to support Bobby's love of bowling but fears she is his bad luck charm when things go awry; Sophie worries baby Barbara is not smart enough.
Caroline's ex-boyfriend, Candy Andy, shows up at a press junket being held to promote the film about Caroline's life; Bobby gets jealous over Caroline and Candy Andy's reconnection.