A lot of girls move to New York City to "make it." Max and Caroline are just trying to make their rent. Two girls from very different backgrounds - Max, poor from birth, and Caroline, born wealthy but down on her luck - wind up as waitresses in the same colorful Brooklyn diner and strike up an unlikely friendship that could lead to a successful business venture.
Max (Kat Dennings) is a witty mid-twenties waitress who has had to work hard her entire life. Caroline (Beth Behrs) is the high society daughter of a Bernie Madoff-esque investment advisor who is now facing justice. With nowhere else to go, the formerly wealthy Caroline gets a job at Max’s Brooklyn restaurant and the two girls become friends. Although they can barely afford the rent, they dream of raising enough money to open a cupcake business together.
Now that Caroline and Max are both living and working together, the girls must figure out how to maintain proper boundaries. Max reluctantly allows Caroline to share her bed, but is very upset when Caroline finishes breaking up with Robbie for her, denying Max her long-awaited break-up scene. Their cupcake business also hits a snag when Max refuses to put her name "out there” as a way to promote sales. When Caroline accuses her of having a fear of success, the two girls temporarily part ways. Later that night, though, Caroline confesses to Max that the cupcake dream is all she has. Max agrees to give it another shot, and Caroline invites Robbie back the apartment so that Max can have her break-up scene after all.
Max takes Caroline to the Goodwill for her first shopping trip as a broke girl. She complains at first, but she is quick to embrace the bargain hunting allure of thrift store shopping. When someone steals a shirt that Max was excited to buy, Caroline vows revenge. As Caroline and Max grow closer, Caroline begins treating Max like one of her friends from when she was rich. When Max proves to be a poor shoulder to cry on and blows off a 2-for-1 manicure, however, Caroline starts questioning how strong their friendship actually is. In the end, she learns that Max is a true friend even though she shows her affection and loyalty in unusual ways.
Noticing that her teeth have started to spread, Caroline laments the fact that she left her dental night guard in her townhouse when she left. After chiding her for having "rich people problems,” Max agrees to help Caroline break into her old bedroom and get it back. With Johnny’s help, they manage to get inside and Max is exposed to the extravagance of Caroline’s former life for the first time. The situation gives Max new respect for her friend, because she now knows just how much Caroline was forced to give up. Meanwhile, Max tries to sabotage Han’s efforts to bring Karaoke to the restaurant.
When Caroline learns that Max has been dodging bill collectors for years, she devises a plan to get her friend’s finances back on track. Inspired by an 80’s themed hipster party they discover in a laundromat, the girls throw a ‘90’s horse party’ in the diner with a stiff cover charge. The plan causes Caroline to come face-to-face with a ‘Bill’ of her own – her ex-boyfriend William who left her when her father went to jail.
Tired of sleeping on the couch every night, Caroline buys a Murphy bed kit for the living room. Wanting to make sure she learns self-reliance, Max tells her to assemble it herself. After trying and failing, she calls Johnny up and asks him to come over and help her. This freaks out Max, who shared an awkward moment with him in the diner and has his napkin doodles pinned up all over the apartment. While Caroline attempts to learn how to do things herself, Max tries to learn how to promote her cupcake business. Inspired by Caroline’s smooth sales techniques, she finally gets up the nerve to ask Peach if they can cater an upcoming party.
Encouraged by the comments of some upscale patrons at the diner, Max and Caroline attempt to sell their cupcakes to a trendy Brooklyn coffee shop. They are summarily rejected because the cupcakes aren’t pretty enough. Undeterred, Caroline signs them up for a cake decorating class at an Italian bakery. Max masters the skills it would take to make her cupcakes more beautiful, but the girls discover that another approach – cupcakes with insulting phrases on them – might be even more lucrative.
Caroline decides to get a second job as a personal organizer in order to make some extra money, but is freaked out when her first client turns out to be a hoarder. Meanwhile, Johnny asks Max to be his lookout when he tags his latest billboard. They share a romantic moment above the New York City skyline, but just when Max is ready to admit to herself that she has feelings for Johnny, she learns that he already has a girlfriend.
Caroline and Max finally catch a break with their cupcake business and get a job catering for Johnny’s art opening at a local gallery. Their happiness is short lived, however, when Max kisses Johnny after swearing that she was going to get over him for good. Now, Caroline and Max must serve cupcakes to Johnny, his guests, and his girlfriend while the guilt of their liplock is still fresh in their minds.
When Peach leaves town for the holidays and Caroline breaks Max’s mixer, the girls decide to get a new second job in order to help pay for their Christmas expenses. They get hired as department store elves and are told to report for their first day at 3AM on Black Friday. But after Caroline's father tells her not to visit him in prison on Thanksgiving, the girls’ stressful new job puts Caroline's holiday spirits to the test.
With the New York City winter fast approaching, Max tries to convince Caroline that it’s time to find a new home for Chestnut. Not wanting to lose her pet, Caroline attempts to build a shelter for the horse in their yard. When that fails, the girls temporarily move Chestnut into Max’s room. With time running out, the girls are forced to turn to an unlikely source for support: Peach.
When Max’s oven breaks, Caroline decides to sell one of her designer gold rings in order to buy a new one. When the gold store is only willing to pay a fraction of the ring’s value, however, Caroline decides to try and return it at the department store where she bought it. When that plan fails as well, the girls attempt to hold an illicit ‘pop-up sale’ in the bathroom of the department store to auction off the ring. But when some of Caroline’s old friends show up and the sale is put on hold, Max starts to doubt her partner’s true commitment to their business.
While on a shopping trip, Caroline is aghast to find out that Max uses coupons to help reduce the cost of food. Her outrage is short lived, however, when she realizes just how much money can be saved by clipping coupons. Over the next few days, Caroline becomes a coupon diva, buying up anything she can as long as the price is right. Max’s patience is tested when Caroline, instead of taking a trip to visit Chestnut like she promised, goes head to head with the self-proclaimed "Coupon Queen” of Brooklyn. In the diner, Max fights what she perceives as injustice when Han raises the price of tampons in the bathroom from a quarter to seventy-five cents.
When Max's upstairs neighbor turns up dead, Caroline is startled to learn that her friend has never bothered to meet anyone in their building. She bribes Max into giving out cupcakes as a gesture of neighborly goodwill, but the plan is interrupted when Sophie, the new tenant, moves in upstairs. Hostility between Sophie and the girls begins almost immediately, as Max responds to increased noise levels by writing a very threatening letter. When Sophie threatens to call the landlord on the girls, however, Max realizes that they’re the ones who might be facing eviction if they don’t make peace.
When Sophie offers the girls an opportunity to join her cleaning company part time, Max and Caroline jump at the chance to make more money for their cupcake business. But before they are allowed to work for one of Sophie’s real clients, she tests their abilities by making them clean her apartment.
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 tries to pass off her cupcakes as kosher when she and Caroline serve them at a boy's Bar Mitzvah.
Max joins Caroline on a trip to visit her father in prison.
Max and Caroline take a two-day spring break ‘vacation’ from their other jobs in order to dog-sit in an upscale Williamsburg apartment. While attending a party that evening, the girls take on new identities in order to feel like they are truly on vacation from their lives. But when Caroline gets a food blogger interested in their cupcake company, Max has to choose between a possible break for their business and finishing the only vacation she’s ever had.
Max tries to convince Caroline to come with her to an experimental drug trial as a way to make some extra money. She refuses at first, but relents after finding out that she will have to hire an expensive lawyer to represent her in a deposition related to her father’s case. When Caroline starts experiencing the drug’s side effects during the deposition, it’s up to Max to step in and save the day.
It’s the night before taxes are due, and Caroline has agreed to help Earl file his return. Inspired by receiving the first formal check addressed to their cupcake business, Max decides to file her taxes too – for the first time ever. Caroline agrees to help Max as well, but is quickly overcome by how disorganized Max truly is. Everything from her oversized purse to her financial history is a complete mess. Meanwhile, the girls try to help Oleg, who has fallen in unrequited love with Sophie.
The girls struggle with their priorities when Caroline tells Max that they should skip some of their housecleaning jobs in order to help promote their cupcake business. Max is against it, believing that skipping out on paid work in order to give out free samples and business cards is a waste of their time. Their issues come to a head when Caroline signs them up to make a batch of incredibly difficult buttercream cupcakes without asking Max first. And because the order is for Peach, Max’s babysitting job is in jeopardy if the cupcakes aren’t perfect.
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.
In the one-hour season finale, Max and Caroline use Caroline's invite to a Manhattan gala as a means to meet MARTHA STEWART (guest starring as herself) and present their cupcake business. Recurring guest star JENNIFER COOLIDGE appears as Sophie.