The narrator begins this chapter with an interlude on the difficulty of writing on what is "dark, mysterious, and undocumented," but she reaffirms her duty to "state the facts" and let the reader think what he or she will.
In the summer following the disastrous winter after the Great Frost, Orlando is exiled from Court and is in deep disgrace with the powerful nobles. One June morning, he fails to wake at his usual time, and remains, as if in a trance for seven days. When he finally awakes, he is different; he has forgotten much of his past life. He chooses to live in solitude for months, allowing no visitors but his servants. His servants hold him in high regard and curse the Russian princess for bringing their master to this state. Orlando spends his time among the crypts of his ancestors, meditating on death, and moving in a deep depression. His love of literature sustains him, as he reads constantly during this period. The narrator describes reading as a "disease which preys upon his system." Orlando tries to write as well, but "happily" because he is of a strong constitution, the disease does not destroy him as it destroys so many other failed writers.
Orlando is smitten with writing, and by the time he turns twenty-five, he has written over forty-seven plays, romances, histories, and poems, mostly involving "some mythological personage at a crisis in his career." But now, as he dips his pen in the ink, he pauses, and the narrator comments that "it is these pauses that are our undoing." He thinks of the fat, shabby man he saw years ago at his house when the Queen came to dine, and he wonders who the man was. He guesses the man was a poet. Orlando stands and vows to be the first poet of his race, and to bring immortal lustre to his name. He struggles with his composition, thinking himself a great fool one moment, a great genius the next.
Overcome with the prospect of being a writer, Orlando decides to suspend his solitude. He asks his friend, who has connections to writers, to deliver a letter to Nick Greene, a very famous author of the time. Much to Orlando's delight, Greene decides to visit him. In Orlando's grand house, which has welcomed the richest and the most noble, Mr. Greene looks small and awkward. He is short, stooped, and lacks the good-looking air of nobility. Orlando is at a loss for how to place him. They go to dinner and try to discuss the family relations that may bring them closer together on the social scale. Greene goes on and on about his infirmities, and mentions that poetry is very hard to publish. Though this is the period where Shakespeare, Marlowe, Donne, and Jonson are writing or have just recently written, Greene maintains that the great age of literature is past in England. Too many poets, he complains, write for money instead of "Glawr."
Orlando abandons all hope of discussing his own writing with Greene, but he is amused by the drunken, amorous anecdotes of all his literary heroes. Though he holds some pity and contempt for all Greene's rude mannerisms and bawdy language, Orlando thinks his conversation is a great improvement over the boring discussions of the nobility. Ironically, Greene feels smothered by the peace of Orlando's estate, and thinks that he will never write again if he does not escape such repose. Greene leaves and Orlando promises to pay his pension. When Greene gets back to his busy household, he writes a satire about a lonely nobleman, one who is clearly modeled on Orlando. It is published and when Orlando reads it, he vows he is done with men. He sends for dogs to keep him company.
Orlando decides he is fed up with love, women, and even literature. He burns almost all of his written works. He decides to let nature, his dogs, and reflective questions about life take up all his time. In this way, he passes many years until he is thirty years old. Though he is healthy, he has been consumed by the "lethargy of thought," which forces him to reflect upon life rather than act. Finally, after admitting that he has been deeply hurt by Nick Greene, he vows to write only for himself, not for any critic. He decides to write about his home, and he thinks that his ancestors have been noble to allow themselves to die in obscurity. Orlando feels that his ancestors have done well by improving their family estate, so he decides to follow their lead and refurnish his home.