Ruby Matthews just turned thirty and realized her life isn't what she wants anymore. She's a teacher who's lost her love for teaching. Her whole life she's wanted to be a writer, but she knows that breaking into that career is almost impossible. Chase Donahue is a hot shot divorce lawyer who is battling for a partnership in his firm. He's overlooked because his firm is looking for a partner that fulfills their strong family image, and Chase is the eternal single playboy. In a decision of haste, he lies and tells his bosses that he's engaged and ready to settle down. Having to keep up his ruse, he decides to reach out to Ruby, a girl from a previous date gone wrong, and offers her a deal of a lifetime. The deal gives both of them a chance to get what they want. All they have to do is pull off a fake wedding and convince everyone that they're actually in love.