The clouds that Orlando saw turn out to be spread over the entire British Isles. They do not move, and they create a terrible climate where everything is damp, chilly, and gloomy. Fashion, architecture, and cuisine change due to the chill. Ivy grows everywhere, and men and women become more separate, speaking in euphemism if at all. Women's lives are marked by birthing and raising children, as many as eighteen by the age of thirty. Literature also changes, with works becoming much longer. The biographer references the memoir of a man named Eusebius Chubb, who witnesses how nature is getting out-of-control due to the climate and then kills himself.
For a while, Orlando holes up in her house in the city and tries to pretend life can be the same as in the eighteenth century. One afternoon, she is driving through a park when she comes upon a statue of a fully clothed man and a partially clothed woman, surrounded by a collection of strange objects. She finds it awful to look at. She looks down and is shocked to see that she is wearing male clothing, so she hurries to her country home to change. She tells the new housekeeper, the Widow Bartholomew, that she finds it chilly, and they discuss Queen's Victoria's pregnancy by euphemistically referring to a crinoline. Orlando recalls being in the same house with Queen Elizabeth, and she trips while deep in thought. She blushes as she realizes that she will need to buy herself the materials to make a crinoline skirt as well as a baby cradle, meaning she must be pregnant as well.
She takes out the manuscript of "The Oak Tree," which the biographer blasély notes she has now been working on for "close on three hundred years" (208). She thinks about how her style has changed over time, but some things, like her love of nature, have never changed. She tries to write finds it difficult, stopping and starting and dripping spots of ink on the paper, perhaps because the servants are working noisily in the room. Then, she suddenly writes three stanzas in beautiful script. She is so alarmed by such a flow of "involuntary inspiration" (210) that she knocks ink all over the page. She feels a strange tingling that starts out all over her body but focuses on the finger where she would wear a wedding ring—if she were married. She feels ashamed for not being married, which she has not felt in the past, and when the Widow Bartholomew comes into the room she asks to see her wedding ring. The Widow refuses, flinging her hand away.
Now, when Orlando goes around the city, she sees wedding rings everywhere. Orlando buys a wedding ring and wears it, but her finger continues tingling and she cannot sleep or write. Orlando comes to believe that she has a "spirit of the eighteenth century" (214) and that the nineteenth century "broke her" (214). Orlando continues to wear a crinoline, which impedes her movement. She becomes nervous and fearful, and ultimately she decides that she would like to get married. She thinks about marrying the Archduke, among other men, but she rules them all out for various reasons.
Orlando goes for a walk, lamenting all the while that everyone else but her has a mate. She finds a bird feather on the ground while walking, so she puts it in her hat. She sees more feathers and follows them up a hill. She begins to run, and then she trips, breaking her ankle. Rather than feeling hurt, she is ecstatic; she embraces the ground, declaring that she is "nature's bride" (220) and that death is better than love or fame. Suddenly, she hears the sound of a horse's hooves. A man rides toward Orlando on horseback, stopping just short of trampling her. A few minutes after meeting, Orlando and the man get engaged.
The next morning at breakfast, Orlando and the man introduce themselves to each other. The man's name is Marmaduke Bonthrop Shelmerdine, Esquire. They feel as if they already know everything of importance about each other because they are so in love. He is a sailor, and he is only in England because of the direction of the wind. At the same moment, Orlando pronounces that Shelmerdine is a woman, and Shelmerdine pronounces that Orlando is a man. They both protest, but then go back to talk about Shelmerdine's voyage. Orlando cries as Shelmerdine tells her about his sailing adventures on Cape Horn, and she thinks to herself "I am a woman...a real woman, at last" (223).
They continue talking about trivial matters, and soon the butler comes into the room to announce that two officers have arrived. The officers present Orlando with the result of the legal cases against her. The marriage to Rosina Pepita has been annulled and the sons’ claims to inheritance overturned. Orlando’s sex has been “pronounced indisputably and beyond the shadow of a doubt...female” (225). Orlando stops reading at the section about marriage and heirs, declaring neither will exist. While Orlando’s wealth has decreased greatly due to the legal fees, she is officially considered to be noble again. When the news of the lawsuit’s conclusion gets out, many people—nobles and commoners alike—celebrate, but Orlando pays little attention. Instead, she spends most of her time in the forest with her lover, Shelmerdine. They continue to talk about Shelmerdine’s travels on Cape Horn and enjoying how alike they are, especially in that they both transgress the behavior of a particular gender. The biographer notes that Orlando called her lover different things depending on her mood.
After nine days of relaxing together, the wind starts back up, meaning Shelmerdine will need to leave soon. Orlando and Shelmerdine run to the chapel and get married while the wind blows crazily outside.
The beginning of Chapter V is heavily laden with metaphorical imagery. At the end of Chapter IV, the biographer describes a huge cloud that begins to gather over London as midnight strikes on the eve of the 19th century, writing, "A turbulent welter of cloud covered the city. All was darkness; all was doubt; all was confusion. The Eighteenth century was over; the Nineteenth century had begun" (199). In Chapter V, the narrator describes the effects of this cloud, which it turns out "hung, not only over London, but over the whole of the British Isles" (200). These effects include nature growing rapidly, women retreating to the home and having more children, changes in clothing and hair customs, and life in general feeling chilly and damp. These changes are meant to metaphorically describe life in England in the 19th century, which was a much more oppressive and stifling time than the 18th century, particularly for English women. Virginia Woolf was born in 1882, meaning her upbringing was affected strongly by the trends of the early and middle 19th century.
A parallel of note between Chapter V and Chapter IV are moments in which Orlando interprets the meaning behind collections of seemingly random objects. In Chapter IV, Orlando opens an old Bible found at her house and finds a spot of blood, a clipping of hair, and a crumb of pastry. Orlando adds a pinch of tobacco from her Turkish pipe and then marvels: "Hair, pastry, tobacco — of what odds and ends are we compounded" (157). During this same scene, Orlando is preoccupied with how she is growing up and losing her prior illusions, so the collection of objects seems to instill her with a sense of wonder about the twists and turns of life. The parallel moment in Chapter V comes when Orlando is riding from London to her country house. She sees "A conglomeration of heterogeneous and ill-assorted objects" including "memorial wreaths, trousers, whiskers, wedding cakes, cannon, Christmas trees, telescopes..." (204). Rather than the positive emotions she feels while looking at the small collection in the Bible in Chapter IV, Orlando now finds the juxtaposition of random objects "so indecent, so hideous" (204). If a reader interprets this reaction as again reflecting Orlando's feelings about the twists and turns of her own life, this moment reveals Orlando's discomfort with her life's lack of consistency and purpose.
A motif that reemerges in Chapter V after a long period of inactivity is the particular behavior of lovers. The biographer particularly stresses that words themselves have little meaning during conversations between those deeply in love. This idea was introduced during Orlando's infatuation with Sasha; the biographer then wrote, "They would walk of everything under the sun...Nothing was too small for such converse, nothing was too great" (39-40). In Chapter V, a very similar description from the biographer accompanies Orlando's first conversation with Shelmerdine: "They talked for hours or more...really it would profit little to write down what they said, for they knew each other so well that they could say anything, which is tantamount to saying nothing, or saying such stupid prosy things as how to cook an omelette..." (224). Since the reader knows how deep Orlando's love for Sasha was, when this motif emerges during Orlando's early meetings with Shelmerdine, it signals to the reader that her feelings for him are very serious.
Societal preoccupation with sex and gender differences is parodied in Chapter V through the legal cases mounted against Orlando when she returns to England. It is alleged that Orlando cannot own land both because she is dead and because she is a woman, and the equal footing given to those cases humorously demonstrates that, in 18th-century England, a live woman had the same legal rights as a dead male. Besides highlighting the absurdity of women's low social status, the legal cases also poke fun at how gender and sexual identity are shaped and perceived by law and by society. The biographer describes Orlando getting the results of the cases, writing, "'Ah! what about sex? My sex', she read out with some solemnity, 'is pronounced indisputably, as beyond the shadow of a doubt (what was I telling you a moment ago, Shel?) female" (225). From Orlando's internal musings throughout the book, it is clear that Orlando's gender will never be "beyond the shadow of a doubt." Her gender has always been quite fluid and is clearly shaped moment-to-moment by her feelings, dress, and experiences. Nevertheless, this legal distinction is of great import, since one's legal gender will dictate one's legal and financial agency. Furthermore, while Orlando gets to keep some of her money and property, it is stated in the letter that this wealth is "entailed upon the heirs male of [her] body" (225). This demonstrates how the societal disenfranchisement of women legally passed from generation to generation.
In Chapter V, the reader gets a rare glimpse of Orlando's writing. While her writing is discussed much throughout the book, direct excerpts are rarely included in the story. Orlando is having difficulty writing, and then suddenly writes three stanzas of poetry in a script that seems almost not her own. It seems that she is possessed with a poetic spirit, or perhaps feeling the strong influence of literature of the time. The first two stanzas of the poem have an irregular rhythm, one instance of perfect rhyme, and a lofty tone. The lines are short, consisting of lines of 6-8 syllables, except for the last line of the second stanza, which stops abruptly. In contrast, her third stanza strictly keeps iambic pentameter, meaning there are 5 pairs of stressed and unstressed syllables per line. The poem forgoes perfect rhyme, and perhaps the most prominent poetic device is alliteration, such as in the line "Bright burning blushes, torches of the tomb" (210). Iambic pentameter was particularly popular in the 15th and 16th centuries, so this third stanza might be read as an unconscious rejection of 19th-century poetry. To be certain, the style of literature Orlando read as a young man greatly affected the way she writes later in life, as demonstrated by Nick Greene's praise of her writing in Chapter VI.