Ollie Trinke (Affleck) is young and at the top of his game as a music promoter. He is both a workaholic and a silver-tongued expert at manipulating the press. At a company Christmas party, Ollie meets Gertrude Steiney (Lopez), a book editor for a New York publishing house. They are instantly attracted to each other, and begin a whirlwind romance that changes the course of his personal and professional life.