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Orlando fights a Moorish head dangling from his attic ceiling. He longs to eventually fight in great wars. He belongs to a very old and distinguished English noble family. The year is in the late 16th century.
Orlando works on some of his poetry, then runs off into the woods to hang out underneath a big oak tree.
He meets Queen Elizabeth, who falls in love with him and gives him all sorts of money and fancy titles.
Orlando joins the Queen at court and turns into a bit of a lady-killer until he falls in love with a Russian princess named Sasha.
Sasha stomps on his heart and Orlando runs back to his big castle all depressed.
He falls into a mysterious weeklong sleep.
When he wakes up, he keeps to himself and writes poetry.
He invites a poet named Nick Greene for a visit.
Greene exposes Orlando’s literary gods as quite ordinary men.
At the end of Greene’s visit, Orlando finally summons up the courage to ask for the poet’s opinion of a play he wrote called The Death of Hercules.
Greene takes it, goes back to London, and writes a scathing satire of Orlando’s whole way of life.
Orlando becomes more depressed. After some time, he decides to redecorate his entire castle.
After he’s done redecorating, he invites people over to party 24/7.
While everyone is partying, he hangs out in his room and works on his poem "The Oak Tree."
As he does so, he realizes a very tall woman has been stalking him.
He invites her in for some wine and learns that her name is the Archduchess Harriet, and she seriously has the hots for him.
Orlando leaves the country to become an ambassador in Constantinople. King Charles is now the ruler of England.
After becoming a duke, Orlando falls into a mysterious weeklong slumber. When he wakes up, he’s a woman.
She runs off to roll with the gipsies for a while.
Realizing that her love of nature and her pride in her big house are incompatible with the gipsies’ way of life, Orlando goes back to England.
On her journey there, the full force of what "being a woman" means in English society hits her.
When she arrives in England, she’s slapped with many lawsuits due to her sex change.
When she gets home, Orlando sits down to work on "The Oak Tree," but the Archduchess Harriet shows up.
That would be the Archduke Harry to you. Turns out he was a man all along, and he still has the hots for Orlando.
Orlando is upset that, as a woman, she can’t just run him through with a sword and be done with it.
She resorts to cheating, lying, and manipulation to get rid of her unwanted suitor.
After getting rid of Harry, Orlando decides to pursue life and a lover, and takes off for London.
She parties hard with the elite society, then hangs out with the great writers of the day (Pope, Dryden, Addison) before realizing they’re all not that cool and have no real respect for her intellect.
She begins dressing as a man and befriends a couple of prostitutes.
A cloud descends upon London and the nineteenth century begins.
The Victorian era isn’t for Orlando; she constantly feels pressure to yield to the "spirit of the age," which we learn involves getting married. Only problem is, there are no eligible men out there.
Orlando turns to nature instead, but in the process twists her ankle and meets Marmaduke Bonthrop Shelmerdine, Esquire (Shel for short). Two minutes later, they’re engaged.
Since her husband spends his time sailing around Cape Horn, Orlando doesn’t get much happy married time before Shel takes off.
The lawsuits restore all of her property back.
Orlando finishes her poem "The Oak Tree," hops into her car (invented when we weren’t looking), and drives off to London looking for someone willing to read the manuscript.
She runs into Nick Greene, who is now a respected literary critic. He thinks the poem is wonderful and promises to get it published.
Orlando experiences great literary success and fame before realizing that fame has nothing to do with writing poetry.
The novel ends with Orlando baring her chest to the moon and calling for her husband.