Chapter II begins with the story’s fictional biographer acknowledging that little is known about Orlando’s life during the period following the Great Frost. He is exiled from Court and returns to his family’s house in the country. One day in June, Orlando does not get up in the morning and is found to be in a trance, not even breathing, for seven days. On the seventh day, he wakes up at his usual time in the morning and acts like nothing unusual happened. However, the people of his house note that, during the time that he was in a trance, something seems to have happened to his memory, as he now gets confused and distracted when people speak of the Great Frost, Russia, princesses, or ships. The biographer muses on the nature of sleep and its relation to death and then returns to the story of Orlando, describing how he began spending his time in extreme solitude, even worrying his servants. Orlando becomes fixated on death and spends a lot of time in the crypt where his ancestors are kept, thinking about how little physically remains of great people of the past. Sometimes, down in the crypt, Orlando weeps over Sasha.
During this time, Orlando also takes up reading a lot, which had been a passion of his since childhood. The biographer informs the reader that people saw reading negatively at the time: they viewed it as a disease that caused people “to substitute a phantom for reality” (66), which was especially pitiable for a nobleman with many expensive possessions. Orlando writes as well, working on at least 50 different texts that he keeps hidden in a wooden cabinet. Orlando pauses as he is about to write, and the biographer says that this pause is “of extreme significance” (69) because tiny choices can affect one’s future in big ways. In the moment that Orlando pauses, he thinks about Sasha, but he substitutes the face of the man he once saw writing poetry in place of hers. Orlando suddenly decides that he must become a famous poet himself so that he will be remembered after his death. He commenced this pursuit with vigor, changing his style back and forth, feeling sometimes like a genius and sometimes like a fool.
Only after years of solitude does Orlando decide to contact a friend in London named Giles Isham, hoping to use this connection to set up a meeting with a well-known author named Nicholas Greene whom Orlando admires. Nicholas Greene agrees to come to Orlando’s house to meet. Orlando is disappointed when Nicholas Greene arrives because his clothing is shabby and his manner somewhat undignified. Something about the visitor makes Orlando ashamed of his lavish lifestyle, and he tries during a long conversation about Greene’s lineage to drop in the detail that his grandmother was a commoner. When the conversation moves to the subject of poetry, Greene becomes suddenly animated, and he talks enthusiastically about the nature of poetry, contemporary poets, and, somewhat out of the blue, his own health issues. His main argument is that poetry is dead in England because in the past authors wrote for “la Gloire” (78), or glory, whereas contemporary writers such as Shakespeare, Marlowe, Ben Jonson, Browne, and Donne write for money. Nevertheless, Greene greatly enjoys telling anecdotes about the famous writers, whom he knows personally, and Orlando enjoys hearing them.
Greene stays at Orlando’s house for many weeks, and the two do silly things together like playing musical instruments and toasting cheese in the fireplace. Then, one day, Nick Greene decides that if he doesn’t leave Orlando’s house and get back to the city immediately, he will never write poetry again. Orlando is both relieved and regretful to see Greene go, and he finally finds the courage to give Greene the manuscript of one of his plays to get his opinion on it. Orlando promises to pay Greene’s pension quarterly, and Greene leaves happy.
When Greene gets home, he decides to write a satirical piece about Orlando’s life. Greene not only “roasted” (84) Orlando by parodying the way he acted and spoke in private, but he even includes passages from Orlando’s play that he finds poorly written. The pamphlet is published and eventually gets passed along to Orlando, who reads the entire story and then instructs a servant to buy two elk-hounds from Norway because he is “done with men” (84). The servant returns in three weeks with the dogs, the female of which has puppies on his first night at Orlando’s estate; from then on, Orlando gives up literature and spends time only on dogs and nature. He burns everything he has written, besides one poem called "The Oak Tree" that he wrote as a child. Then, every day for years, he climbs the hill near his home to sit under his favorite oak tree to look out over England and witness the changing of the seasons. As he sits, he contemplates deep questions such as the nature of love, friendship, and truth, and the biographer notes how time can contract and expand depending on one’s mental state.
During this period, Orlando turns 30. However, the biographer notes that the calculation of age makes no sense because of the different ways one can experience time, which meant that “Some weeks added a century to his age, others no more than three seconds at most" (87). Orlando ponders whether it is better to speak plainly or use metaphors. He continues to be plagued by shameful memories, particularly Nick Greene ridiculing his poetry. He decides that, from then on, he will not write for anyone else's pleasure but his own, and he concludes that fame is actually an impediment.
Looking out from the hill, Orlando sees his fancy, sprawling home, and he is suddenly struck by the work his ancestors have done to develop it. He decides that since there is no more building to be done, the way he can make his mark on history is to furnish it beautifully. He redecorates it lavishly; the biographer includes an excerpt from a ledger book listing items such as "seventy yellow satin chairs" (95) and then says that it would be too boring to describe all of Orlando's actions during this time. Eventually, Orlando finishes decorating the house, and he decides that the only thing it lacks is people. He throws a series of parties for the noble people living nearby, which result in him becoming well-liked and taking a number of political offices. However, he still craves solitude as much as ever; during these parties, he often goes up to his room and works on his poem, "The Oak Tree." It is slow-going now, and the biographer notes that his style has changed.
One day while Orlando is working on the poem, he looks out the window and sees a woman walking in a private courtyard of his home. He is intrigued to see her, and even more so when she appears twice more in the following four days. The third time, Orlando goes outside and confronts her, finding that she looks like a hare and has "a stare in which timidity and audacity were most strangely combined" (99). She introduces herself as the Archduchess Harriet Griselda, and, as she and Orlando go inside together to become acquainted, Orlando notices that she often laughs in a strange, nervous manner. When they part ways, the Archduchess promises to return the next day; for the next three days, Orlando avoids meeting with her. On the fourth day, it rains, so Orlando has to let her in. During their time together, the Archduchess bends down to fit a golden shin case to Orlando's leg; Orlando becomes overwhelmingly aroused and has to leave the room. Orlando thinks about whether he is feeling love or lust; he decides it is lust, so he sends a footman to send the Archduchess away and avoids her for the next few days. Even remaining in his house, he sees images of her everywhere, so he asks King Charles to make him an Ambassador and send him to Constantinople. The King agrees and Orlando sails away.
It is notable that the narrator says that the present day while she is writing Chapter II is November 1, 1927. When reading Chapter II for the first time, this may seem only to underscore once more that the book is supposedly a biographer from a distant time period. However, Chapter VI takes place in the 1920's, with the final line of the book being, "And the twelfth stroke of midnight sounded; the twelfth stroke of midnight, Thursday, the eleventh of October, Nineteen hundred and Twenty Eight" (292). This would mean that the final chapter takes place after the biographer has begun to write the book and that it is possible for the biographer to have known Orlando personally. This adds complexity to the relationship between the biographer and the subject.
Many of the characters in Orlando are explicitly written to parody, criticize, or call attention to certain aspects of culture. One of the clearest examples of such a character comes in the form of Nicholas Greene, the renowned writer whom Orlando invites to stay at his house. Nicholas Greene is such a broadly written parody that he could almost be thought of as a caricature. He is described as disappointing to meet in person, which is something Woolf repeats later in the novel when Orlando meets various other famous writers and wits. Greene is fond of complaining, especially about the poor state of writers in the 17th century, and Woolf alludes to writers who are still respected today, such as Shakespeare, to drive home the wrongness of Greene's accusations. Woolf will continue this parody later in the book when Greene, as a much older man, levies the same complaints against 20th-century writers while celebrating writers of the 17th century, showing that he is not a genius but merely someone who is constantly nostalgic for past eras of literature.
During Greene's stay with Orlando, Woolf continues her parody by having the guest repeatedly mispronounce a literary and cultural term. Woolf writes, "No, [Greene] concluded, the great age of literature is past...In such ages men cherished a divine ambition which he might call La Gloire (he pronounced it Glawr, so that Orlando did not at first catch his meaning)" (78) and later emphasizes, "There are still a few left of 'em — who take antiquity for their model and write, not for pay but for Glawr.' (Orlando could have wished him a better accent.)" (80.) La Gloire literally means glory in French, but the word had deep class significance. During the 16th and 17th century, aristocrats and high-class artists were able to focus on La Gloire rather than working for money. Thus, Woolf's critique of Greene actually has multiple layers of distaste. Not only does Greene show his aristocratic inclinations, which Woolf critiques in characters throughout the book, but his shabby dress and mispronunciation of La Gloire also show that he is not as high-class as he pretends to be.
Woolf's preoccupation with time appears at many points in this chapter. Woolf first plays with the reader's sense of time by saying that "Some weeks added a century to [Orlando's] age, others no more than three seconds at most" (87). Since Orlando will live to be over 300 years old and should be over 100 years old at the time this quote appears in the story, it is clear that aging is not treated in a realistic manner in the novel. In addition, many small but significant details in Chapter II have symbolic ties to the concept of time. Orlando enters a coma and rises on exactly the seventh day, giving significance to the span of a week. Later in the book, he will again enter a coma for exactly seven days, emphasizing that the amount of time was not randomly written, but specifically chosen for the thematic and biblical significance that a week connotes. Furthermore, Woolf writes that Orlando's house has 365 bedrooms (the approximate number of days in a year) and 52 staircases (the number of weeks in a year). These details deepen the sense that Orlando and Orlando's home somehow function outside of natural time.
Orlando flees England at the end of Chapter II because of the emotions he feels for Archduchess Harriet. On the surface, it seems that Orlando is merely revolted by his own feelings of lust where he would rather feel love. However, Orlando has already passed puberty, and is likely not virginal in any sense, having consorted with (at least) Sasha, Sukey, and the girl with whom Queen Elizabeth caught him. After reading Chapter IV, in which Orlando returns to England and finds out that Archduchess Harriet was actually Archduke Harry all along, this scene of disgust and horror builds the theme of Orlando's confusion about his gender and sexuality. Perhaps he was able to intuit that the Archduchess was not actually female, and, like the first time he saw Sasha, he is torn between his attraction to the person and the cultural norms that prevented him from being romantically involved with people of the same gender.