Bring on the tough stuff - there’s not just one right answer.
Compare the first three paragraphs and the last three paragraphs of the novel. In what ways are they similar? In what ways are they different? Can we use them to help us understand the shift in Orlando’s character over the course of the book?
Aside from the whole sex change, how has Orlando changed over the course of the book?
What does Orlando’s biographer/narrator consider to be the problems with the genre of biography? How do we know? Do you agree? Does this novel fix those problems?
How far can we trust the narrator of this text? What pressures is the biographer subjected to? To what extent does the biographer conform to those pressures?
How might the novel be different if Orlando was first a woman and then became a man? Same results?
What’s up with the weeklong sleeps? What transformations do they precede?
On what basis do you think the chapters are divided in Orlando? Can you think of other ways to divide the novel?
Orlando gets to live for several centuries. But random other people also have abnormally long lives – Mr. Dupper, for instance, and Nick Greene. What is the effect of their longevity? Does it add to the novel?
How is foreignness (non-Englishness) treated in the novel?
What is the meaning of the ending with Orlando "baring her breast to the moon"?
In A Room of One’s Own, Woolf claims that the great writers must have androgynous minds. When and how does Orlando achieve this greatness, if (s)he does at all?