Max meets Martin Channing, Caroline’s dad, for the first time when the girls visit him in a white collar prison. They quickly bond, and Martin enlists Max’s help in getting Caroline to attend an auction where the contents of their old townhouse will be put up for sale. Martin tells the girls to buy an old loving cup that Caroline won riding Chestnut as a child, claiming that it is the only item in the auction with ‘real value.’ Believing that Martin stashed some of his money in the cup, Max becomes obsessed with the idea of getting rich quick.
Max and Caroline attempt to keep faith that Martha Stewart, who tasted and liked one of their cupcakes in last season's finale, will call and help support their business. Meanwhile, Caroline loses a lucky keepsake.
Han proves tougher than expected when the diner is held up by a thief. A panicking Caroline doesn’t fare so well, wetting herself in the face of danger after using Max as a human shield. The next day, the two girls decide to sneak into the movies, and Max gets annoyed at Caroline for always putting herself first. As they squabble over which film to see, they realize that Han is there too and decide to follow him in secret. Meanwhile, Peach tries to get Max to start babysitting for her again.
Max and Caroline audition for the reality TV show Cupcake Wars, hoping to use the prize money to start their bakery. Despite Caroline’s seemingly successful branding of their team, the girls soon learn that being on camera is harder than they had thought.
After getting pre-approved for a credit card, the girls struggle to curb their desire to go on a spending spree. After Caroline breaks a heel, she fights the urge to go to Barney’s and get a brand new pair of shoes. When Earl’s adult son Darius visits the diner, Max wants to buy him a suit in order to try and help jumpstart his comedy career. In the end, the allure of the credit card proves too much for the girls.
Max takes Caroline out to lunch at a soup kitchen in a trendy section of Williamsburg. She’s upset at first, but quickly warms to the free food. While eating, the girls spot a hot guy named "Candy Andy” who runs a candy store nearby. They pay a visit to his shop, and sparks fly between Andy and Caroline before their soup kitchen lunch starts making Caroline violently ill. When Andy reveals that he’s a former Wall Street executive who quit finance to follow his dreams, Max realizes that he’s the perfect guy for Caroline. After embarrassing herself in front of him twice, though, Caroline wants nothing to do with Andy.
Caroline goes on a date with Candy Andy, but things turn sour when he fails to make any advances toward her. When Caroline starts to doubt her date’s sexual orientation, Max decides to pay him a visit and see why he seems to have cooled on her friend. Meanwhile, Max meets two confused and naive Amish boys in the diner who are on their Rumspringa year. When she learns they have no place to say, Max offers to let them crash in the apartment if they’ll build a barn for Chestnut in exchange.
Thanks to the blurb from Martha Stewart, the girls find themselves awash in cupcake clients for the first time. When the soup kitchen next to Candy Andy’s shop goes out of business, Caroline urges Max to consider renting it out so that they can take their business to the next level. Max is on board, but the girls still need to raise enough money to make it happen. After unsuccessfully hitting up Sophie for a loan, the girls consider egg donation as a cure for their financial woes.
As the girls struggle to prepare their new cupcake shop for its grand opening, Caroline decides to hire an intern to help out. Remembering her own days as an intern, Caroline is hard on her new employee. Max, who still can’t fathom acting like a boss, lets the intern get away with anything.
The girls throw a grand opening party for their new cupcake shop. While Caroline tries to get influential people in the community to come, Max uses it as an opportunity to show her ex-boyfriends how far she’s come. When Johnny shows up, Max is shocked to find that he didn’t get married after all – and is still interested in her. Sophie also shows up at the party, believing it is a going-away party for herself since she is going to be spending the next month checking out her newly completed dream house in Poland.
Business is still poor at the cupcake shop, and Sophie’s life isn’t going much better – she refuses to eat or leave her apartment after learning that her contractor swindled her and her dream house in Poland is just a façade. Sympathetic to her plight, Max offers to make her a silent partner in the cupcake shop in order to cheer her up. Sophie is excited by the prospect, but Caroline gets upset when she learns that Sophie’s idea of being a silent partner involves making major changes to the shop, including having the girls dress up as cupcakes in order to attract business. Meanwhile, Max advises Andy on the perfect setting to proclaim his love to Caroline.
The girls are late making the December rent on their cupcake shop, but both are still optimistic that business will pick up during the holiday season. When a series of parties doesn’t help to improve business, though, Max decides to take matters into her own hands and sell cupcakes door-to-door to people who just bought weed from her drug dealer. Caroline is firmly anti-drug and hates the plan, but she changes her mind when she realizes how urgently they need to raise money. When Caroline gets high by accident, however, Max realizes that a stoned Caroline might ruin their chances of raising the money at all.
The girls win a weekend trip to a mountain resort and are excited to have a few days away from the stress of their business. Things get awkward when Caroline accidentally invites Andy along, especially when she lies to him and says that Max was the one who misinterpreted things and invited herself. While Max befriends two gay ‘bears’ at the resort, Caroline and Andy confront some hard truths about their relationship. In the end, Andy feels that Caroline is too focused on the business instead of on the relationship and decides that they need to take a break.
The girls work around the clock to honor a Groupon for their cupcake shop. While the coupon worked to increase business, the girls are taking a loss on every discounted sale and the future of the shop is still up in the air. When they get an order for one thousand cupcakes at full price, the sleep deprived girls enlist the help of everyone at the diner to work all night and get the job done. Meanwhile, Andy and Caroline question whether or not their breakup was the right move, and Max realizes that staying friends with Andy is going to be harder than she thought.
The girls attempt to secure a loan for the cupcake shop. The application requires a letter of recommendation from another small business owner, so Max and Caroline decide to ask Andy for help. They are shocked to learn that he has moved out and his storefront is vacant. While wondering if breaking up with Andy was the right thing to do, Caroline runs into a fortune teller and is told that her future will not contain a great love. With Caroline in tow, Max goes back to try and get a refund, but the fortune teller puts a curse on both of them. Ultimately, the girls reconcile with the fortune teller and get new readings: a vision of the future that might not be perfect, but one in which they can have it all if they continue to share life together.
While trying to get into a rock concert, Max meets a rich, older British man named Graham who works for a record label. After they sleep together, Graham invites Max and Caroline to take his private jet to the Grammy Awards in LA. They accept, and end up flying west with rapper 2 Chainz.
Max and Caroline pay a high price for attempting to remove a street performer away from the entry to their cupcake shop.
Max and Caroline approach Caroline's rich but callous Aunt Charity for money to save their flailing cupcake shop.
When the girls take office temp jobs, Max finds herself being hit on by the boss, while Caroline tries to climb the corporate ladder.
Han fires Caroline after she insults his diner and Max tries to mend their relationship.
Caroline panics when she develops a rash after a night with her ex-beau.
Max and Caroline are invited to be extras on a popular TV show shooting a scene in Han's diner, but when Caroline catches the director's eye, he offers her an actual role - with strings attached.
Caroline's father asks her to go on a talk show to defend him when a former employee threatens to defame him in a tell-all book.
When Max and Caroline offer to deep-clean a previously hidden part of the diner they discover something that could relaunch their cupcake business.