Experienced waitress Max Black meets her new co-worker, former rich-girl Caroline Channing, and puts her skills to the test at an old but re-emerging Brooklyn diner. Despite her initial distaste for Caroline, Max eventually softens and the two team up for a new business venture.
Caroline is tired of sleeping on the couch so she purchases a build-it yourself Murphy Bed. As Caroline attempts to assemble the bed, Max tries to work up the courage to give her cupcake business card to Peach for the twins upcoming birthday.
Max is still in denial over the revelation that Johnny, her crush has a girlfriend, Caroline tries to get her to admit her feelings and let them out. But she says this is what always happens to her - she meets a guy and just when things are getting serious, she learns something like he has another girl. But when Johnny comes to her and kisses her things get weird. And Caroline got them a cupcake order for an art showing which Johnny has a few pieces before learning about what happened. She convinces Max to do it and that she won't have to see Johnny. But they learn ...
Max and Caroline try to find Chestnut a job in order to get him lodging for the winter. Meanwhile, Peach, the mother of the twins Max babysits, auditions for "Real Housewives of TriBeCa."
When Max's stove breaks, Caroline tries to return some expensive rings to Barney's department store, but discovers her surname is no longer an asset at her former home away from home.
Max shows her softer side after seeing Sophie dressed up sends Earl to the hospital with heart attack. Meanwhile, Caroline attempts to rekindle an old flame of hers.
Max and Caroline plan to attend a big fashion gala at the Metropolitan Museum of Art where Martha Stewart is scheduled to be a guest, in an attempt to have her taste their cupcakes and get her seal of approval.