Caroline Channing is a rich spoiled socialite who is shocked to find out her father is charged and convicted for fraud. With no money and no friends, she takes a job in a greasy diner in Brooklyn. There she meets Max, another young waitress who is quite used to being broke. She takes pity on Caroline and lets her move into her tiny apartment.
Though Caroline is not very happy with her new quarters, she is grateful to Max. In fact, she even brings her pet horse with her, Chestnut, the last thing she has from her old life. And thus begins a budding friendship between the two girls.
Caroline realizes that Max is great at baking cupcakes and she comes up with an idea to start their own cupcake business. Since neither of them have any money, they start saving. With the help of their eccentric neighbor Sophie, their friends at work, Oleg and Earl, and their boss, Han, the girls begin making plans for their new business and even cater several parties to make more cash.
Meanwhile, Max tries to help Caroline get used to her new situation. Though it’s not very easy, Caroline soon starts to successfully navigate her new just-above-the-poverty-line life, which involves collecting coupons, working second jobs and shopping at Goodwill.
In the second season, Max and Caroline try to make their catering business more successful. They manage to meet Martha Stewart, who is quite delighted by Max’s cupcakes, and they even audition for Cupcake Wars. Caroline starts dating a handsome candy store owner named Andy. The girls take a risk and rent a space next to Andy’s store and open their first cupcake shop.
Though their new business starts picking up, the girls get buried in debt. Caroline tries to ask for help from her estranged aunt, but she refuses. A rich business woman offers to buy the shop. At first they don’t want to give up on their dream, but when a car crashes into the shop they realize it’s time to let it go.
Caroline’s relationship with Andy becomes more serious, but, after a weekend in the mountains, they break-up, because it seems that Caroline doesn’t see him in her future. They have another one night stand before finally parting ways.
In the season finale, the girls organize a yard sale with the help of their neighbor Sophie, who’s been dating Oleg, the chef from the diner. In order to make some extra money they offer to help Han clean a backroom. After they manage to get rid of all the garbage from the backroom, they realize that the tiny space is perfect for a new cupcake shop.
The girls finally open their new shop – “Max’s Homemade Cupcake Shop”, but the grand opening doesn’t go quite as planned. In fact, a famous British rock star dies right in front of the shop and their fans block its window in order to pay their respects. Despite the rocky start, the new shop seems to be quite popular.
Max decides to apply to the Manhattan School of Pastry and she manages to get in. However, the tuition is $24,000, which is way more than the girls could ever afford. Caroline doesn’t give up and manages to set up a work-study arrangement with Nicholas, the hot chef who runs the school. So, Max starts her studies at the pastry school and Caroline starts working in the school’s office for free.
To no surprise, Max strives at the new school and she even meets a cute boy in her class, Deke. They are just friends at first, but they start dating soon after. Max finds something shocking about her new boyfriend, which, in her mind, it’s a deal breaker – Deke comes from a wealthy family, even though he lives in an actual dumpster. However, Max continues to date Deke and even goes with him and Caroline at his parents’ apartment for a dinner. At the beginning, his parents love Max, but everything eventually goes downhill. Deke’s parents also invite their best friends for dinner, a couple who has lost a lot of money because of Caroline’s father. Max defends her best friend and accidentally spills an embarrassing secret about Deke’s mother. Of course, Deke’s parents are not happy and they demand that his son stops dating Max. Deke sides with his girlfriend and he is cut off. However, Max knows that Deke won’t be able to live without the financial support of his parents, so she breaks up with him and sends him home.
Meanwhile, Caroline is quite happy at her second job at the pastry school, mostly because she gets to spend time with her hot boss, Chef Nicholas. And the attraction is mutual. The two of them start dating, but Caroline finds out that Nicholas is actually married. She immediately breaks up with him, and despite Nicholas efforts to get her back, she won’t hear of it. In the end, Nicholas goes back to France, and the school is shut down.
The season ends with Caroline discovering that Max never graduated from high school and encouraging her to take one last exam in order to get her diploma. Finally, even though she didn’t get to complete pastry school, Max manages to graduate high school with the help of her best friend, and even reconnect with her estranged mother.
The fourth season begins with an interesting offer for the girls. The producers of the popular reality-show “Keeping Up With the Kardashians“ want to shoot a segment at their cupcake shop. Max and Caroline not only get to meet Kim Kardashian, but they also get free publicity for their shop. What is more, the two girls come up with another great business plan – they start making t-shirts with the cupcake logo and they even manage to sell them at a trendy store.
Meanwhile, Oleg and Sophie’s relationship gets serious and Oleg proposes. At the beginning Sophie has some doubts; but the two of them move in together and they start planning their wedding. She also asks Max to be her maid of honor, but Max refuses. However, when the girls are thrown in jail after mistakenly breaking into the wrong apartment, Sophie uses jail money as a bargaining chip. In the end, Sophie bails the girls out and Max accepts to be her maid of honor and even throws her a bridal show, which ends up with the FBI breaking up the party. Turns out, a man in their building has been keeping three women hostage. If only the guy hadn’t worn the girls’ cupcake t-shirt when he was arrested in front of everyone…