Oh, Ollie! is a musically oriented show set in the middle of World War II. A young writer, Amelia Dunne, more famously known as Amelia D. Everly ventures out to start a new life in New York, disguised as a man to conceal her sexuality. She takes her brother’s name, Oliver, who has been enlisted into the war and hasn’t been home in months. She quickly discovers in her new life that hiding her true identity is harder than she thought after falling for her boss’s assistant, Lily Moore. As Lily and she become closer, the war rages on along with her new boss’ suspicions. As her brother suffers more and more, will “Ollie” come clean to her first love or continue to live a lie?