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.moreless
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.moreless
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.moreless
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.moreless
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.moreless
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.moreless
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.moreless
Max and Caroline become zombie extras after they arrive on the movie set in Texas where Randy is working. Back at home, Han and Oleg fire the contractor working on the dessert bar and try their hand at construction.moreless
Max and Caroline stow away and waitress on a riverboat to New Orleans, as they try to reach Randy in Texas. Back at the diner, Oleg and Sophie make big bucks when they sell pony rides on Chestnut.moreless
With Han at the wheel, Caroline accompanies Max as she heads out to Los Angeles to win back Randy. Oleg is left in charge of the diner while Sophie fills in for the girls as a waitress.moreless
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."moreless
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.moreless
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.moreless
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.moreless
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.moreless
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.moreless
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.moreless
Season 5 ends with Max and Caroline learning that Han is in big trouble with a gang for amassing a hefty gambling debt on women's tennis that he can't repay.
Max and Caroline approach the owner of the pizza place next door about renting space to expand their renovated dessert bar.
A law firm that's courting Randy for a job invites him and Max to dinner at a hip new restaurant with eclectic cuisine, but the evening veers off course when things don't sit well with Max.moreless
Max's boyfriend asks to spend the night at her apartment in order to get to know her world better. Meanwhile, Caroline works on getting a liquor license for their dessert bar.
Randy surprises Max at the diner with hopes of patching up their relationship, but Max looks to Caroline to decide for her. Meanwhile, Han sets the girls up with a real estate agent to help them find a bigger space for their dessert bar.moreless
The girls visit Caroline's father in prison to see him perform in a musical and to tell him their plan to use Caroline's movie money to convert their cupcake window into a dessert bar.moreless
Caroline signs away the rights to her life story so it can be turned into a movie. Meanwhile, Max is heartbroken when Randy breaks up with her via his therapist, Elliot, so Caroline rents a party bus in an attempt to cheer her up.moreless
Max and Caroline lose Randy's dog while pet-sitting and risk their lives to find him, while a cannibalistic serial killer is loose in their neighborhood.
Caroline meets with studio writers in an effort to make her life story into a movie, but she is torn when they reveal they would not portray Max in the project. Meanwhile, Max is spoiled by her new Hollywood beau, who sets Caroline up on a date with a friend.moreless
Max tags along with Caroline when she travels to Los Angeles on a film studio's dime to discuss the idea of making her riches-to-rags life story into a movie. While there, Max loses her luggage but finds a new crush.moreless
Caroline shares her riches-to-rags life story on stage at a storytelling night and captures the attention of a Hollywood studio executive. Meanwhile, Sophie and Oleg search for a surrogate.
Max and Caroline sign up to be "Booth Babes" in order to get into a large gaming convention for free. Once inside, they discover Han's friend created video game characters based on them, so they demand compensation.moreless
Caroline falls in with the wrong crowd when she tries to make new friends, after Max reconnects with an old friend.