Breaking up is hard to do, especially after four years together. Taylor Middleton, a singer striving for her big break, and her boyfriend Malcolm Darling, a mover and shaker in the music business, have decided to call it quits. Taylor wants to take her onstage persona—Gracie M—to LA, where she hopes bright lights and big dreams await. But before they break up, the two decide to spend one last night in Chicago, the city where they once shared a passionate, romantic weekend, in hopes of preserving some good memories. In Chicago, Taylor realizes she's not so sure about taking her talents elsewhere, as Malcolm reminds her why she fell in love—and lust—with him. Taylor may soon discover the right man, like music, can set her free and make all her dreams come true.