Orlando buys herself English women's clothes and gets aboard the ship to take her home to England. She reflects upon her new gender and the penalties and privileges it holds for her. She thinks how she can no longer swim now that she wears so many petticoats and she questions whether she feels good or bad about needing manly protection. She feels a tingle when Captain Nicholas Benedict Bartolus offers to cut her meat for her. She questions whether the man's or woman's sexual ecstasy is greater, whether it is better to pursue or flee. She decides it is most delicious to yield and see the Captain smile. But Orlando is dismayed at the time and energy it will take her to make herself presentable (obedient, chaste, scented and appareled) as a woman each day. As a person who has been both sexes, she concludes by censuring both sexes equally; women for their limited role and power in society, men for the way they prance about like lords and become fools the second they see a lady.
The ship anchors off the coast of Italy and Orlando agrees to accompany the Captain onshore. When she returns the next morning, she speaks more like a woman than a man, and it is clear that her romantic interlude with the Captain has made her more feminine. She rejoices in being a woman, happy to take on the blights of poverty and ignorance in order to be free of the manly pursuits of power, happy that she may spend her time on contemplation and love. She finds that even though she is now a woman, she is still in love with women, and she realizes she can understand Sasha better than ever before. But Orlando remains conflicted; she does not want her new gender to require her to hold her tongue and "fetter her limbs" remaining powerless to man.
The ship makes its way to England and Orlando stands in wonder at the sights of St. Paul and the Tower of London, which she has not seen for such a long time. London is much different now in the late seventeenth century than she remembered it more than a century ago. There are shops, paved streets, and many people walking about, talking, and shopping. At a coffee shop, she thinks she sees Mr. Dryden and Mr. Pope (English authors) stopped for a drink. She returns to her home to find happy servants awaiting her (who seem confused but content to serve their mistress as they had their master), and to find that several lawsuits have been brought against her. The chief charges are that one) she is dead, and can therefore own no property, two) she is a woman, with much the same consequences as being dead, and three) that she was an English Duke, whose three sons by Rosina Pepita claimed her property. Orlando does not think much of the charges at the moment, and once at home, she takes to reflecting on her religion (poetry) and her history. She concludes: "I am growing up. I am losing my illusions perhaps to acquire new ones." She decides to start fresh upon her poem, "The Oak Tree."
Orlando looks out her window and sees the Archduchess Harriet, the woman whose seductions led her to flee the country. She laughs at Harriet's appearance, thinking she resembles a "monstrous hare." She invites Harriet in, thinking women annoying, and when she turns around, Harriet has turned into a tall man dressed all in black. The "Archduke Harry" asks Orlando to forgive him for the way he has deceived her. He explains that he has always been a man, and he merely dressed as a woman because he was so in love with Orlando when he was a man. Now he asks Orlando to marry him and travel with him to his castle in Romania. Orlando does not give him an answer, but Harry is persistent, returning day after day, though the two can find nothing to talk about. They take to playing a game in which they each bet money as to where a fly will land. Orlando grows so bored with Harry that she cheats in the game, hoping he will catch her. After the twentieth time, Harry finally catches her cheating and is appalled. Orlando, who is relatively new at being a woman, drops a small toad down his shirt. This enrages Harry and he drives away. Orlando is relieved she does not have to marry him.
Orlando does not really care about her title or fortune. All she desires is "life and a lover." She takes off for London in her coach. Here, the narrator takes a moment to point out that Orlando is changing because of her sex; she is a little more modest about her writing, more vain in her appearance. Her outlook on the world changes because of the clothes she wears, because of something intrinsic to the gender.
When Orlando arrives in London, it is not long before she finds a lover. She goes out for a walk on the mall one morning, when suddenly she finds herself surrounded by a mob of people who know her from reports of the lawsuit. She is distressed as the mob closes in, when suddenly the Archduke Harry arrives to whisk her away. He has forgiven her for the frog incident, and has even made a jewel in the shape of a frog to give to her. Orlando is slightly annoyed that she cannot even go for a walk without Harry asking for her hand in marriage. She returns home to find the cards of many great ladies who desire to make her acquaintance; she is thrust into London society.
Amidst all the balls and engagements that she is invited to in London, Orlando becomes amused and excited. But as she grows accustomed to these engagements, she is saddened; she has found many lovers but no life. She thinks society unfulfilling. The next morning she responds to an invitation from a great lady, the Countess of R—. Orlando longs to be among the society of Addison, Dryden, and Pope, the great writers of the time, and she believes they will be at this party. Lady R. is known to have exclusive parties to which only the very best minds are invited, and where everything that is said is witty. Orlando goes, stays there for three hours, and comes away delighted. Although these people, like everyone else, seem to talk about nothing whatsoever, they are all under the illusion that these are the wittiest, best parties they have ever been to. One evening, Mr. Pope the famous poet comes to join their circle. He says three or four truly witty things in a row and destroys everyone's illusion. They go away saddened.
Orlando invites Pope to drive home with her. During the ride, she vacillates between venerating such a great poet and scolding herself for being so foolish to think that anyone deserves fame. She takes to spending time with 'men of genius' and she discovers that they are much like everyone else. The secrets of writers' souls are written upon their works; they are not so mysterious as people think. She grows tired of spending time with poets, who, she finds, have great minds but often lack the other virtues of magnanimity and humility. Orlando realizes that these men do not really respect her for her intellect.
Alone again, Orlando puts on her old men's clothes of her youth and walks outside. She goes into London where she sees a beautiful woman sitting on a bench. The woman, a prostitute named Nell, thinks Orlando a man and takes her to one rented room. Orlando pities the girl and reveals herself to be a woman. Nell laughs loudly and confides that she is glad because she is not in the mood for men tonight anyway. This begins Orlando's interactions with the prostitute women. One by one, Nell and her friends sit around the punch bowl telling Orlando their life stories. She finds them very entertaining.
Orlando takes to switching genders, and dons male or female clothes depending upon which is more appropriate for the moment. She finds that living in two genders is doubly fulfilling. She uses her male persona to eavesdrop on interesting conversations in coffee houses, like those of Dr. Johnson and Mr. Boswell. At the end of this chapter, she looks out over London and sees a great cloud moving over it. "The Eighteenth Century was over; the Nineteenth Century had begun."
This chapter explores the concept of mismatching. Orlando finds she can bear neither the boring society of Archduke Harry nor the frustratingly witty company of famous poets like Mr. Pope. Feeling hindered by her petticoats, her new gender, and the subsequent loss of all legal property-holding abilities, Orlando travels from poets to prostitutes looking for a group to support her. Yet in this century, she is unable to find her complement.
Chapter Four is perhaps the most comical section of the novel. Orlando has always held writers on a pedestal and when she gets the opportunity to meet some of the great poets of the day, she is thrilled. But the reality of what she finds falls far short of her expectations. In Lady R———'s meeting of important and interesting people, it is necessary to refrain from saying something too witty, lest everyone else feel quite dull. The one man with an ego large enough to say something witty (Mr. Pope) is ironically small, misshapen, and ugly. The carriage scene, in which Orlando reveres Pope's noble brow, only to realize it is a bump in the cushion above his head, epitomizes Woolf's comic irony. The 'truth' Orlando finds is far from what she expects from reading history and poetry. By making fun of those star-struck people in love with the image of intellectuals and great writers, Woolf produces great satiric comedy.