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Orlando uses money from the sale of another pearl to buy noble women’s clothing to wear on her journey home. She travels on a ship called the Enamoured Lady. Orlando reflects on how her clothing presents both limitations and privileges for her now.
Early in the trip, Captain Nicholas Benedict Bartolus approaches Orlando and offers to cut her a piece of roast beef. After considering the differences in sexual appetite and expectations across genders, Orlando decides to flirt with the Captain so that she can see him smile. Orlando bemoans the effort it takes for a woman to be both desirable and chaste.
When the ship anchors off the coast of Italy, Orlando accompanies the Captain onshore. After this romantic interlude, Orlando begins to act more femininely. She is happy to be a woman, despite the difficulties. It allows her to be free of manly pursuits of power, and to be free to “more fully enjoy the most exalted raptures known to the human spirit which are [...] contemplation, solitude, and love” (Chapter 4, Page 119). Orlando reflects on how all her lovers had been women. And despite being a woman, she finds that she still loves a woman, Sasha, though she can now understand her better. Orlando feels conflicted about how her female identity requires her not to speak and act demurely while being powerless when compared to men.
The ship passes through London. Orlando observes places such as St. Paul’s Cathedral, the Tower of London, Greenwich Hospital, Westminster Abbey, and the Houses of Parliament. As she had not seen the city for more than a century, she is struck by how different London is now in the 17th century. Once the ship docks, Orlando begins walking through the city. As she passes a coffee shop, Orlando believes that she sees the English authors John Dryden and Alexander Pope. Orlando continues home and finds her servants waiting for her.
While they are happy to see her and only mildly confused by her transformation, the servants tell her about the several lawsuits that have been brought against her. The major lawsuits charge that she is either dead and cannot own property, that she is a woman and cannot own property, or that she has three sons with Rosina Pepita who seek to claim Orlando’s property. Orlando dismisses the lawsuits at this point, instead choosing to meditate on her poetry and family history. She sits in her library and studies a family heirloom, the prayer book of Queen Mary. Orlando reflects on her growth and maturation, deciding that she must start fresh upon her poem “The Oak Tree” and write what she likes.
When Orlando looks out her window, she sees the Archduchess Harriet. Orlando laughs at Harriet’s looks before inviting her in. Orlando turns her back on Harriet and, when she turns back around, Harriet has revealed herself to be the Archduke Harry, a tall man dressed in black. Harry admits that he has always been a man and only dressed as a woman to be a suitable match for the male Orlando. He then asks Orlando to marry him and travel to his Romanian castle. Orlando does not answer, but Harry persists day after day.
When Harry calls, the pair find they have nothing to talk about, and by the end of the week they turn to playing a game. They bet each other where a fly will land. Orlando cheats by sneaking a dead fly onto her guessed spot, sure that Harry will catch her. Only after 20 games does he notice, and Harry is angered. Orlando drops a toad down his shirt, further enraging him. Harry leaves, and Orlando is relieved that she does not have to marry Harry.
Orlando reflects on how she does not really care about her title and fortune. Since all she desires is to live and love, she takes off for London. On this journey, the biographer observes that Orlando is becoming more stereotypically feminine. Her clothes seem to be inspiring a change in her, suggesting that clothes determine gender identity more than biology.
In London during the reign of Queen Anne, Orlando takes a walk and is mobbed by people aware of the lawsuits against her. Harry rescues her and states that he has forgiven her. As a token, made her a jeweled frog and asks her to marry him. This gesture annoys Orlando, and she returns home.
Once at home, Orlando finds many social invitations and enters London society. At first, she enjoys the balls and meetings, but she quickly finds this life unfulfilling, as she has had many lovers but found no life.
Orlando receives an invitation from the Countess of R—, whom Orlando believes to be associated with the great writers Addison, Dryden, and Pope. As she desperately wants to meet the greatest writers of the time and believes they will be attending this party, Orlando decides to go. She attends and stays for three hours. Orlando is delighted. While all the attendees think that they are witty, they actually talk about nothing at all. One night, Alexander Pope, a famously witty poet, attends. Mr. Pope only says a few truly witty things. With their illusion of wittiness shattered, the attendees leave, saddened.
Orlando invites Pope to drive home with her, which leads to her spending more time with other writers. She becomes tired of spending time with geniuses who lack humility and generosity. She realizes that these men do not respect her intellect.
Orlando disguises herself as an elderly man to take a walk. When she walks through London, she sees a sex worker named Nell sitting on a bench. Thinking Orlando is a man, Nell takes her to a room to have sex. Orlando, pitying her, reveals herself to be a woman, which causes Nell to laugh and confide in Orlando. Orlando befriends multiple women who are sex workers, and the women tell Orlando their life stories.
Orlando begins dressing in stereotypically masculine or feminine clothes as she sees fit for the moment. Living as both a man and a woman is especially fulfilling for Orlando. As a man, she eavesdrops in coffee houses. Looking out over London at the end of the 18th century, she observes a large cloud behind St. Paul’s Cathedral and moving over the city.
Orlando’s return to England also means a return to stricter gender roles. The ship’s name itself, The Enamoured Lady, is a reminder of English society’s preoccupation with gender and gender performance. Orlando buys new noble women’s clothes, suggesting that she is aware of the role she will be expected to play once back in England.
Her experiences on the ship reveal her growing awareness of the new expectations she must live up to now that her body is female. Captain Nicholas Benedict Bartolus’s sexual overtures cause Orlando to reflect upon the need to protect her “jewel” (113)—chastity—that she now upholds as a woman. Reflecting these new limitations, Orlando bemoans the oppressiveness of women’s clothing while also admiring herself in the clothes. This ambivalence about her gender presentation reflects her continued mixture of both genders
Orlando goes back and forth, sometimes criticizing men, sometimes women. She has no strong identification with either gender and finds fault with both sexes. As a woman, she must now “pay in my own person for those desires” (115) that she had as a young man. Yet she is critical of the “sacred responsibilities of womanhood” (116) to look desirable while being chaste.
But while she dislikes the misogyny she experiences now, she enjoys the extra attention from the Captain. Her romantic interlude with the Captain onshore suggests that Orlando’s sexual appetite is constant across genders, despite female stereotypes. This experience results in Orlando acting more feminine, suggesting she can now understand something of the female experience after using her female poetry in a decidedly gendered act. As a result, Orlando is happy to be a woman so that she is free to “more fully enjoy the most exalted raptures known to the human spirit which are [...] contemplation, solitude, and love” (119). These desires reflect Orlando’s shifting goals to live for herself.
The changes in the London skyline symbolize the dramatic changes to English culture over the decades that Orlando was away. Passing all the iconic structures of London prompt her memories, leading her to reflect on her past experiences and beliefs. Her shock at such a transformed city reflects the changes she has also undergone.
Orlando’s lack of concern about the lawsuits against her reflects how she no longer cares for titles, money, and property. Instead, Orlando looks forward to the anonymity these suits provide so that she can live in solitude. The servants’ insignificant response to her gender change underscores how superficial this change was and how the core of Orlando’s identity is still recognizable.
Orlando’s meditation on her family’s heirloom, Mary Queen of Scots’s prayer book shows how authors leave little pieces of themselves throughout their writing. The queen has left a “blood-stain,” a “lock of hair and a crumb of pastry” (127). But the reader, too, leaves a part of themselves, as “Orlando now added to these keepsakes a flake of tobacco” (127). The religious nature of the prayer book inspires Orlando to look at her own work as a reflection of her own poetic beliefs, which she equates to her religion. As a result, Orlando reflects on her own growth and maturation, which prompts her to restart her own poem to reflect her new identity.
Orlando’s second set of encounters with Harriet underscores the importance of change. Upon first seeing her, Orlando notes how “[n]ot a hair of her head was changed” (131). The reveal that Archduchess Harriet is Archduke Harry is not a transformation like Orlando’s; instead, it is a reveal, as Harry had been a man all along.
Their relationship parodies many aspects of a romance novel of the time. Both Orlando and Harry “acted the parts of man and woman” (132), but neither is successful. Orlando notes, “If this is love, [...] there is something highly ridiculous about it” (132). Harry displays more emotion than is thought “manly” at this time in history, and Orlando refuses to submit to a man. Their incompatibility in the game suggests that they are not a good match. When she places the toad down his shirt, she equates Harry more with the frog than with the prince of fairy tales.
As a result of her stereotypically feminine clothing, Orlando begins to act more like is expected for a woman. The biographer describes how clothes are “more important offices than merely to keep us warm” (138). As suggested by Orlando’s thoughts on the ship ride back to England, clothes place limitations and expectations upon the wearer, and the biographer also notes that they “change our view of the world” (138). The biographer claims to disagree, instead inserting their own opinion that clothes “are but a symbol of something hid deep beneath” and that “a change in Orlando herself that dictated her choice of a woman’s dress and of a woman’s sex” (139). They describe how the sexes “intermix” as every person is a “vacillation from one sex to the other” (139). This claim reveals the biographer’s nuanced view of Orlando and gender more broadly.
When Orlando dresses herself in her clothes from her boyhood, the clothes still “fitted her to perfection” (157). This perfect fit suggests that, despite the changes Orlando has undergone, she is still fundamentally the same person. The sex worker Nell’s identification of Orlando as a man and her acceptance of Orlando as a woman further underscores that gender does not define Orlando’s identity and is a fluid aspect of her person.
The clouds moving over London at the turn of the century foreshadow Orlando’s difficulty conforming to the nineteenth century. Orlando will struggle with the more staid and conservative Victorian era.
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By Virginia Woolf