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.
Once all 365 bedrooms are refurnished, all fifty-two staircases are redone, and the entire house is gleaming, Orlando invites his neighbors to stay with him and earns their good opinion. He laboriously works to add to his poem "The Oak Tree" and his writing is now much improved, less ornate.
One day, Orlando sees a very tall woman riding by his window. He goes to investigate and finds she is a Romanian archduchess named Harriet, a cousin of the Queen's. He invites her into his home and is suddenly overcome with passion for her. But he is repulsed that this feeling is lust rather than love. Orlando does not know what to do, so he asks King Charles II to send him as an Ambassador to Constantinople. He decides he must leave the country.
In Orlando, Woolf satirizes the genre of biography. She believes that biographies are too concerned with extraneous details, and have a limited sphere of reality. Chapter Two opens with the biographer admitting her difficulty in writing of this part of Orlando's life, which is "dark, mysterious, and undocumented." While she claims that the first duty of the biographer is to "plod in the indelible footprints of truth" without looking right or left, she acknowledges that she must "state the facts as far as they are known" and let the reader make of them what he will. These words, by our biographer/narrator are Woolf's way at poking fun at Victorian biographers (like her father) who think they are recounting the factual truth. To negate the idea of 'factual truth, recounted objectively' is one of Woolf's main purposes with Orlando.
The tone of the novel is light-hearted satirical. Throughout, Woolf includes allusions poking fun at other authors, her contemporaries, and even her own work. In Chapter Two, the narrator suggests the simple statement "Time passed" might help one more quickly reach the conclusion that in a period of many years, nothing whatsoever changed. This is an allusion to Woolf's previous work, To the Lighthouse, in which she includes a chapter merely mentioning that "time passed." Such frequent allusions to her own work and to the work of contemporary authors suggests that Woolf was writing with the audience of her friends in mind. Vita Sackville-West and the rest of the Bloomsbury group, a circle of intellectual, well-educated people, would have been the most likely to find humor in the novel's comic allusions. Although many of the jokes make Orlando most appropriate for Bloomsbury readers, the interesting themes and entertaining story allowed the novel to be accessible to a wider audience. At the time of publication, the Orlando was extremely popular, selling more than double the number of copies as Woolf's previous novel.
The novel explores the difficulty of finding fulfillment. In the period of Orlando's life covered in Chapter Two, the protagonist turns from love to literature in an attempt to find fulfillment. Orlando lives through four centuries and many adventures, but always he is searching for "life, and a lover." Writing becomes his outlet for both his frustrations and his reflections. It is through art that he expresses his love of nature, his worries, and his essence. In Chapter Two, Woolf describes the writing process, which involves the rigors of reading, crossing out, editing, adding, and reading again thousands of times. The narrator describes Orlando as being affected by the "disease" of reading. After putting so much of himself into his writing, Orlando is heartbroken that he is laughed at by a critic. Much like Woolf herself, Orlando is horribly fearful of criticism. Yet Orlando perseveres in his writing; he carries his manuscript with him on all his adventures. The completion of his poem signifies a personal maturity, a fulfillment of his desire for artistic expression.