Virginia Woolf wrote this as a love letter. It's sometimes silly, sometimes insightful, often thought-provoking and probably was groundbreaking. It is said to be the most charming and longest love letter ever written. It's important to read a little bio of the author before reading Orlando. A fun read, very glad I read it. Now I know why they wondered "Who's Afraid of Virginia Woolf?".
From Amazon:
Begun as a "joke," Orlando is Virginia Woolf's fantastical biography of a poet who first appears as a sixteen-year-old boy at the court of Elizabeth I, and is left at the novel's end a married woman in the year 1928. Part love letter to Vita Sackville-West, part exploration of the art of biography, Orlando is one of Woolf's most popular and entertaining works.
A total acid trip of book. Virginia Woolf at her strangest.