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 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.

The women and the diner gang prepare for the premiere of the film about Caroline's life; Caroline and Max contemplate their future at the diner.