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.