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The biographer laments the lack of information available regarding Orlando’s activities in Constantinople; the best sources only tell us that Orlando was very important and an active ambassador.
Oh well, says the biographer, we might as well use our imagination.
The biographer guesses that Orlando’s days in Constantinople begin at seven in the morning with a smoke.
As he smokes, Orlando admires the city and watches it wake up for the day.
Then he thinks about how Constantinople looks very, very different from England.
Orlando is amazed that he can admire such a foreign landscape.
After his morning smoke and reflection on the city’s beauty, he gets all dressed up for the day and receives important visitors until lunchtime.
The biographer informs us that no intact records of these visits have survived.
After eating a massive lunch, Orlando goes to visit important officials. He runs through a diplomatic gauntlet at each house, involving lots and lots of small talk and ending with fake smoking and fake drinking. Although these visits never concern any substantive matters, Orlando goes through with them until late into the evening.
The biographer notes that Orlando performs his diplomatic duties very well, but depression frequently sill creeps up on him.
Based on rumors and legends, the biographer tells us that Orlando has a tendency to talk to his dogs in English, work on "The Oak Tree," and run around the city in a disguise.
The biographer tells us that Orlando becomes a legend around Constantinople.
While he may be a legend, Orlando still doesn’t have any close friends.
After two and a half years of great ambassadorship, King Charles calls in a promotion for our hero and grants Orlando a Dukedom.
This leads to a lengthy discussion about a raging party hosted by Orlando.
When Orlando puts on his new crown, everything falls into "disorder." The biographer laments that the lack of historical evidence prevents additional description.
What we do know, the biographer says, is that Orlando goes to bed at his usual time. Some say he locked his door, others say they heard music, and a washer-woman saw "a man’s figure" out on the balcony, inviting up a peasant woman for a little…you know…
The next day, Orlando is found sound asleep in the middle of his messy, messy room. He continues to sleep, despite a doctor doing all the doctor-y things he can think of to make Orlando wake up.
Orlando’s secretaries take this excellent opportunity to look through all of his stuff.
They find some business papers, some "Oak Tree" writing, and then (gasp!) a marriage certificate between Duke Orlando and a gipsy dancer named Rosina Pepita.
Orlando continues to sleep.
After a week, revolution breaks out in Constantinople, and angry Turks run around abusing all the foreigners.
The angry Turks find Orlando, but think he’s dead, leaving our hero free to sleep another day.
The biographer wishes that the story ended right here, but continues to tell Orlando's story out of respect for Truth (yes, the kind with a capital T).
To make a long story short, despite the pleas of some women named Purity, Chastity, and Modesty, Truth wins out. Orlando stands up and we can "see" that he is now a woman. And not just any woman, mind you – a hot woman.
His figure combines "in one the strength of a man and a woman's grace."
Chastity, Purity, and Modesty make one last stab at hiding Orlando’s body, but they fail.
Orlando looks at himself (from here on out to be referred to as "herself") in the mirror and then goes to take a bath.
The biographer interrupts to tell us that aside from now having a woman's physique, Orlando remains exactly the same person. She has the same memory and the same abilities as the male Orlando. Having been a man of thirty years old, she is now a woman of thirty years old.
The biographer leaves the whole sex and sexuality stuff aside and moves on to consider Orlando.
She dresses in Turkish garb, which is unisex.
Orlando is unfazed as she considers her new position. She gathers up some of her poetry, feeds her dog, stashes a few pistols in her purse, and grabs some of her most expensive jewelry. She then whistles out the window and leaves her house.
An old gipsy is waiting for her with a donkey. Orlando leaves with him.
After some unspecified adventures, Orlando meets up with a group of gipsies that she had allied herself with.
She lives the life of a gipsy for a time, and they accept her as one of their own, teaching her how to make cheese, weave baskets, and snare birds.
Although she could have married among them, over time it becomes clear that Orlando has a very different philosophy towards life than the gipsies. She loves the beauty of nature, while the gipsies have no words for beauty.
The old man who brought Orlando away from Constantinople is named Rustum el Sadi. He suspects that she worships nature, which is a big no-no in these parts.
Realizing that what she loves is incompatible with the gipsy way of life, Orlando feels increasingly isolated and longs to write. She makes her own ink and proceeds to write in the margins and blank spaces of "The Oak Tree."
Writing makes Orlando happy, but her duties among the gipsies begin to suffer, and they soon want her out of their camp.
One night Orlando describes her beautiful, huge house and how she can trace her noble ancestry back four or five hundred years.
The gipsies are polite, but act as though Orlando has just revealed something shameful.
After Orlando leaves the tent, Rustum follows her and explains that the gipsies still think she’s OK.
Orlando realizes that being able to trace your descent for only four or five hundred years is incredibly shameful. The gipsies can trace their families back at least two or three thousand years.
The gipsies also see ownership of land and a massive house as being particularly vulgar and wasteful. When the entire world is available to live on, why would you just want to live on one little part of it?
Orlando counters their arguments by calling them savages, which greatly contributes to a lot of bad feeling between them.
Orlando becomes confused. She doesn’t want to go back to her old way of life, but the gipsy way of life is increasingly intolerable.
One midsummer morning when she is minding her goats, Orlando has a vision of a summer day in England, complete with deer and insects.
After an extended vision of England, Orlando bursts into tears and tells the gipsies that she has to go home.
This is good timing on Orlando’s part because the young gipsies were ready to slit her throat.
Orlando sells off a pearl from her necklace and bids the gipsies good-bye.