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Now wearing women's clothing, Orlando hangs out on the deck of a ship bound for England.
The captain offers to have some awning stretched out for her, and Orlando realizes that feminine clothing comes with some irritations and some benefits.
The biographer is quick to point out that Orlando is not having the normal feminine thoughts of how to preserve her chastity. Having been a rather amorous (or promiscuous) man, preserving chastity does not consume Orlando’s thoughts.
For the rest of the voyage, she attempts to figure out her thoughts and approach towards her new sex. She jumps back and forth between enjoying her new sex and being restricted by it: she realizes she looks great, for instance, but the same clothes that make her look so good prevent her from swimming in the sea.
Also, he must trust her well-being and protection to others. She asks herself: do I object to that?
Over dinner, Orlando finds her answer as Captain Bartolus offers to cut a slice of beef for her.
Orlando feels a shiver of pleasure run through her, remembering her pursuit of Sasha. Now she is being pursued; she attempts to decide which she likes better.
She declines the captain’s offer of beef and enjoys watching him frown.
She then says, OK, cut me some beef, and he smiles.
Orlando rhapsodizes over the delights of resisting and yielding, thinking she just might throw herself overboard in order for others to rescue her.
In parentheses, the biographer notes that mature women do not have these thoughts; Orlando is simply playing with her new identity.
She remembers that the sailors she used to hang out with have a distinct name for such women, which the biographer decides is much too crude to repeat.
Orlando is upset that she must now respect the opinion of the other sex (men), no matter what.
Upset, she remembers that, as a young man, she had insisted that the opposite sex be "obedient, chaste, scented, and exquisitely appareled." Now that Orlando is a woman, she realizes that meeting these requirements demands a great deal of exhausting discipline. She outlines some of the procedures: hairdressing, being laced into corsets, changing outfits…li>
She stamps her foot and her skirt flies up, exposing part of her leg. A sailor on the mast of the ship almost falls off when he sees her leg. Orlando gets depressed, realizing that the sight of her ankles could cause a man to die.
She decides she should keep her legs covered up, but then feels irritated – why will a man die if she fails to cover up her beauty?
She swears, and then realizes that she has to give that up too, along with beating up men, sword-fighting, wearing crowns, sentencing men to death, and leading armies.
Depressed, she thinks her sole activity once she arrives in England will be to pour tea for men and make sure it’s to their liking.
With horror, she realizes that she has a very low opinion of men. She ends up condemning both sexes based on her unique vantage point of having been both sexes.
She is ready to run back to Turkey and the gipsies, but the ship stops in Italy.
Captain Bartolus invites Orlando to join him onshore.
She goes. When she returns, she stretches out on her couch underneath her lovely awning, with her skirts carefully covering her ankles.
We learn that she’s now more accepting of being a woman.
Soon, Orlando falls asleep.
She decides it’s better to be a woman. She doesn’t have to rule the world, love power, or be educated.
She loves being a woman, which the biographer describes as extreme folly. Neither men nor women should be proud of their sex.
Yet, Orlando pauses, thinking of love and how her sex change allows her to now understand Sasha.
The captain interrupts her thoughts to point out the English shore.
Orlando swears. Luckily the captain attributes it to her long absence from England.
Orlando’s emotions are complicated at this point. She thinks of her past as a duke, ambassador, and fighter, contrasting it with her current well-dressed state as a supposedly helpless woman.
As she approaches England, she feels guilty, an emotion she had never experienced as a man.
From the ship, she sees a white marble dome and thinks of the shabby poet she saw on the way to meet Queen Elizabeth.
Her hand goes to her chest where she has stuffed the pages of her poem "The Oak Tree."
She forgets all about the distractions of her new sex and thinks instead only of poetry.
Captain Bartolus points out various landmarks.
Orlando revels in these sights after such a long time living the life of a gipsy.
She cries as she sees the site of the royal carnival and remembers Sasha. She tries to restrain her tears at first, but then remembers it’s OK to cry now that she’s a woman.
As the ship draws closer, Orlando sees that the landscape has changed. The formerly dreary and disorderly streets are now pleasant thoroughfares.
Orlando arrives on shore.
As soon as she reaches her home in Blackfriars (her city house), she learns of a number of lawsuits against her.
The three most major are: 1) that she is dead and not entitled to any of her property, 2) that she is a woman and not entitled to any of her property, and 3) that she was a Duke married to Rosina Pepita and fathered three sons, all of whom want the property now that their father is dead.
Orlando promises to fight all the charges in court, which will take time and money.
All her properties have been confiscated except for her country house, where she has permission to stay.
She arrives in December and all the servants, including Mrs. Grimsditch and Mr. Dupper, come out to greet her. They’re beaten to the punch by Orlando’s old elk-hounds.
Mrs. Grimsditch is confused and alternates between calling Orlando "My lord!" and "My lady!"
Everyone is happy about her return, and no one evinces any suspicion that Orlando is not the real Orlando.
Mrs. Grimsditch is particularly pleased with the idea that her master is now a woman – maybe household matters will be better looked after.
As the servants gossip, Orlando wanders through her house, re-acquainting herself with everyone.
Happy, she goes to the chapel, sits in an armchair, and opens her prayer book, which used to belong to Mary Queen of Scots.
Inside the prayer book is a lock of hair, a bloodstain, and a crumb. As Orlando smokes, she adds tobacco to the book. She contemplates this random collection.
Sitting in the chapel, Orlando contemplates God. She doesn’t believe in the usual gods, but has a faith of her own. She believes above all in the power of poetry.
She admits out loud that she is growing up.
She heads to her bedroom and thinks of her past.
As she stands at her window, the complexity of life overcomes her.
The next morning, Orlando is ready to work on "The Oak Tree" when an old friend shows up.
Orlando invites the Archduchess Harriet in and the two ladies chat.
Orlando thinks angry thoughts about all women as she gets some wine. When she turns around, the Archduchess reveals herself as a man named Harry.
Orlando suddenly remembers her own womanhood and says that she’s shocked and afraid.
Archduke Harry begs forgiveness.
The biographer cuts all the description short to say that the two of them "acted the parts of man and woman for ten minutes."
We learn that the Archduke had seen a picture of Orlando and came to England to woo him. Now that Orlando is a woman, it will work out great.
The Archduke calls Orlando "the Pink, the Pearl, the Perfection of her sex" and proposes.
Orlando looks at Harry skeptically as Harry begins to cry. He apologizes and tells Orlando he will come again.
He visits Orlando every day to declare his love. Other than that, the two have nothing to say to each other.
Finally, Orlando, out of sheer boredom, proposes that they play a game called Fly Loo, in which they gamble large sums of money betting on which lump of sugar a fly is likely to land upon.
Morning after morning, the two of them watch flies circle around the ceiling until one of them eventually lands on a lump of sugar.
Orlando gets frustrated with this stupid way of passing time. Sick and tired of spending her mornings watching flies, and irritated that she can no longer just beat the guy up, she resolves to cheat at the game.
She catches a fly, attaches it to a lump of sugar, and then, when the Archduke isn’t looking, swaps it for the lump that she bet on.
Since cheating while gambling is highly dishonorable, Orlando figures the Archduke will soon catch on and get out of her life.
The Archduke can’t tell the difference between a dead fly and an a live one.
Orlando wins a lot of money until she practically beats the Archduke over the head with her deceit.
The Archduke is predictably upset and begins crying. He doesn’t care about the fortune, but he does care that she cheats at Loo. He can no longer love her.
But since she’s a woman, he’ll forgive her everything and he apologizes for his harsh language…and Orlando drops a toad down his shirt.
Then she laughs at him.
The Archduke leaves, which is the response Orlando was hoping for.
With the departure of the Archduke, Orlando feels quite alone and demands life and a lover.
She proceeds to doll herself up, then orders a carriage be prepared for a trip to London.
The biographer takes this opportunity to discuss how clothes affect the way we see the world and how the world sees us. Orlando is now treated as a woman because she wears female clothing. She also carries herself differently because she wears female clothing.
The biographer points out that elements of both sexes are present in everyone. Orlando exhibits this tendency particularly strongly, and the biographer informs us that we cannot tell if she is more of a man or more of a woman.
After she arrives in London, Orlando goes for a walk in the Mall.
People of the lower class spot her and crowd around her – she’s famous because of the lawsuits against her.
She’s in trouble now because ladies aren’t supposed to walk alone in public.
The Archduke Harry saves her. He’s forgiven her and even had a little jeweled toad made to show his forgiveness. He proposes again.
Orlando drives home incredibly mad. Why can’t she go for a walk without being accosted by a crowd and proposed to by an Archduke?
When she gets home, Orlando sees a bunch of invitations from ladies in high society.
Orlando begins partying with the top tier of English society. Queen Anne is now the monarch, and society has strict rules about behavior.
The biographer notes that since Orlando’s handling of a rose bowl was enough to win over Queen Elizabeth, one might suppose that Orlando does well in high society.
Wrong! Orlando too often thinks about poetry when she should be thinking about her manners.
It is June and Orlando is upset that life continues to elude her. She talks it over with her spaniel, but the spaniel unfortunately can’t respond.
She accepts one last party invitation, but only because the hostess is famed for having lots of poets at her parties. It is rumored that everything said at her parties is witty.
Orlando shows up. Everyone there is very distinguished and intelligent. She leaves after three hours.
The biographer tells us that we must want to know what happens during the party. Apparently, the guests all think that they're witty, but it's not at all true.
Orlando goes to two more of these parties and believes that she’s listening to brilliance, even though it’s just an old man complaining about his leg.
A small man enters the room. Immediately everyone feels uneasy.
The biographer informs us that the small man said three things so witty that they blew everyone away. In fact, the biographer can’t even repeat them, they were that witty.
The witty man is Mr. Alexander Pope.
Everyone leaves the party is shock.
Orlando invites Mr. Pope to go home with her.
Riding together in her carriage, Orlando alternates between thinking she’s the luckiest girl and the world and thinking that she’s being completely foolish.
We should add that the alternating of foolish/lucky coincides with the carriage’s position on the road. When Orlando is under a streetlight, she realizes her foolishness. When the carriage is in the dark, she’s back to thinking she’s luckier than a rabbit’s foot.
Throughout the carriage ride, Orlando and Pope engage in some small talk. When they reach Orlando’s house, the sun has risen. (With all that light, she must really see her foolishness now.)
The biographer notes that genius is not particularly constant. Pope may have said three witty things during the party, but that's no guarantee of future cleverness. When he’s not being a genius, he’s actually quite ordinary.
When Orlando realizes this, she’s rather disappointed because she now spends most of her time with men of genius: Addison, Pope, Swift, etc. She realizes they’re as human as everyone else. She pours tea for them and sometimes entertains them in her country house.
Her writing changes and improves.
One day when she's serving tea to Mr. Pope, Orlando thinks about how women in the future will envy her.
She then realizes that her thought implies that she’s not exactly enjoying her task at hand. First of all, she hates tea. Secondly, despite his genius, Mr. Pope isn’t exactly a great person. In fact, it’s because of his genius that his other attributes are rather stunted.
Remembering that these witty men have extremely condescending attitude towards women, Orlando resorts to plopping the sugar cube in Mr. Pope’s tea.
He recognizes the action as an insult and writes a scathing satire, condemning Orlando’s entire sex. He shows the draft to her and Orlando feels like Mr. Pope has physically struck her.
Orlando strolls outside to her garden. She meditates under a willow tree until nightfall, then goes into the house and leaves a man.
Well, she leaves wearing men’s clothing. The night is lovely and Orlando still has hope of forging genuine human connections.
Orlando goes to Leicester Square and bows to a young lady of fashion. She looks at him as a woman might look at a man. Well, actually, she looks at him more like a prostitute might look at a man. She takes him home while faking timidity and hesitation the entire time. Orlando can tell that the girl is faking because Orlando is also a woman.
The girl’s name is Nell. When she gets home, Nell goes to change into something more comfortable, if you know what we mean.
When she re-emerges, Orlando takes off her disguise.
Nell finds this hilarious and immediately drops her whole timid act and talks straight with Orlando, telling the noblewoman her entire life story. Orlando is well entertained, although Nell could never be considered a wit, and she has never heard of Mr. Pope.
A bunch of other prostitutes join the little party, and Orlando hangs out with them frequently. They are about to tell her all that they desire, but a man interrupts them to say that women desire nothing.
The biographer points out that most men believe that women cannot seriously enjoy the company of other women because they are completely dependent on men.
The biographer shrugs his (or her) shoulders and leaves it to the men to prove that Orlando could not possibly enjoy hanging out with Nell and her friends.
The biographer details the difficulties of chronicling Orlando’s life at this point.
Apparently, Orlando is engaging in cross-dressing all over the place in different costumes to have various adventures in London. Lots of rumors abound of her adventures.
Orlando is absorbed in watching a play
Home one night after her adventures, she goes to her bedroom and looks out the window. The atmosphere is clear.
Midnight sounds and a cloud descends over London.
When the last stroke of midnight dies away, the nineteenth century begins.