In the late 1950s, at a fictional university in the UK, David, a medical student, and Alison, who is studying geography, fall in love after meeting at a "Freshie" dance. Theirs is a storybook romance—they share common goals and values, they like and respect each other, the relationship is good, and each is warmly welcomed into the other's family. They marry, have children, and eventually, emigrate to southern Ontario where David joins a medical practice. Life is good.

But for David there is an unfulfilled longing. A longing that goes all the way back to his childhood when he wished he had been born a girl. As an adult, his desire to live as a woman takes the form of cross-dressing on the rare occasion an opportunity presents itself. Late in life, with the help of a psychologist, he comes to understand that he is transgender, and Julie Ann is born.

Alison and Julie Ann's marriage must change throughout the transition, but their mutual love and respect endures as they embark on a new life.

Lady in Waiting is a story of love, longing, denial, disillusionment, despair, and ultimately, acceptance and joy. It is a story of transition, transformation, and transcendence.