Nearing the end of her long existence, ninety-five year old Natalie Greenbaum – big band vocalist and jazz singer, wife, mother and a lesbian – reflects on the events of her life, the people she has loved and her personal struggles and triumphs during the tumultuous decades of the mid-20th Century, a time when homosexuality was considered a form of mental illness and even criminal behaviour.
Starting in the spring of 1929 when Natalie is nineteen years old, the story unfolds of Natalie's first love affair with Eva, daughter of a wealthy and prominent family, and her marriage of convenience to an older man, a career Navy seaman. Natalie winds up having a brief, passionate affair with another Navy wife, then has a daughter by her husband. A few years later in 1937, while working as a band vocalist, Natalie meets the mysterious and glamorous Esther – and embarks upon yet another passionate, but ultimately tempestuous and dangerous affair.
Natalie winds up in another brief, intense, but unexpected affair with the wife of her dear friend and employer. Meanwhile, Natalie's husband Thom is promoted to officer and transferred to Pearl Harbor. After a (very) brief career on Broadway, Natalie and her daughter travel to Honolulu in the fall of 1939, where she encounters a tomboyish, yet charming aviatrix named Bonnie...and the next chapter of her life begins.