At the outset of the novel, we're at a crossroads: the biographer has given us all of the ingredients of a heroic life. Orlando's attractive, brave, and looking for love. We'd be forgiven for thinking that this is going to be a swashbuckling romance. But then − the biographer must "admit a thousand disagreeables which it is the aim of every good biographer to ignore" (1.2).
What are these "thousand disagreeables?" Orlando's thoughts. Because he's a writer, the biographer can't avoid mentioning his internal life, even though it's not conventional. The initial situation of Orlando is like a derailment of a traditional biography: we're all set to hear about Orlando's external accomplishments when the biographer reluctantly starts revealing internal revelation.
Orlando's a writer, right? That's his initial situation. But once he meets Sasha, he can't stop telling her that she's "a melon, a pineapple, an olive tree, an emerald, and a fox in the snow all in the space of three seconds" (1.26). We go into language in Sasha's "Character Analysis," so we'll just say here that it's definitely a problem when a writer can't find the right words. Orlando doesn't know Sasha − and you know what they say about only writing what you know.
Orlando's first failure of language is definitely not his last. Losing his illusions about love, he turns back to poetry. Here's where the complication comes in. In our initial conflict, Orlando couldn't find the right words for Sasha. Our complication arises when he discovers that the words he has chosen don't work.
Orlando tries to turn his language to that oldest of inspirations, love, but that doesn't work out. He gets so upset at Sasha's betrayal that he slips into sleep for seven days. If Sasha was his failed first love, then maybe we can read this temporary coma as a failed first death. All this love and death and rage drives him to start churning out tragedies.
Orlando decides he wants to commune with other poets. Having lost the affection of Sasha, he wants to substitute admiration from a peer. So he invites well-known poet Nick Greene to his home. Nick stays just long enough to collect material for a brutal satire of our young hero and his tragedies:
And if there had been any doubt about [the identity of the subject of the satire], Greene clinched the matter by introducing, with scarcely any disguise, passages from that aristocratic tragedy, the Death of Hercules, which he found as he expected, wordy and bombastic in the extreme. (2.29)
(Bombastic is another word for high-flown or pretentious.) So, Orlando wants to be a writer, but he's had his confidence undermined on two fronts: he's failed in love and in poetry. Where is all of this going to lead?
You may ask what does Orlando's gender have to do with this whole writing plot we've been tracing? The conflict and the complication have all been about alienating Orlando from his identity as a writer. And to be honest, he may not have been that great a poet to start with.
We can tell how far Orlando is from being the writer he set out to be by the third chapter, because we're no longer included in his private reflections. He starts thinking strange things about anonymity, and, as though to prove his point, his words get knocked out of the story entirely. At this important moment when Orlando's being named a duke, the narration is handed over to the letters and diaries of other people we've never heard of. So we've really gone a hundred and eighty degrees from Orlando as this sensitive, melancholy poet with whom we're becoming intimate to Orlando as this distant historical figure. But then…
He stretched himself. He rose. He stood upright in complete nakedness before us, and while the trumpets peeled Truth! Truth! Truth! we have no choice left but to confess − he was a woman. (3.37)
Orlando as he had been has been thrown out of the novel, and a new Orlando, a more truthful Orlando has come in to take his place. Orlando's male self has hit rock bottom, so the novel has to do something drastic to end the decline and start again.
We know that, of his 57 poetical works, the only one Orlando found worth keeping after his run-in with Nick Greene was "The Oak Tree." Now that he has become a female and ditched her post as Ambassador to Constantinople, are we going to see "The Oak Tree" again? The suspense after Orlando changes into a girl comes from our curiosity about what kind of woman Orlando is going to be.
Orlando's gender switch seems at first to be a bit like a reset button: she submerges herself in the wild landscapes that had originally prompted her, as a boy, to become a poet. In fact, it's her rediscovery of her poetic desires that makes it impossible for Orlando to stay with the gypsies she traveled with after fleeing Constantinople. They are suspicious of her romantic notions and critical of her.
As soon as Orlando picks up her pen again, she starts rebuilding herself, making a new female version of Orlando. She's has a recipe: throw in love of nature, add a million new lines in the margins of "The Oak Tree," mix, and serve. Other ingredients include her family history and England itself. And where would Orlando be without sex? There's a fair amount of that going on, too.
The suspense over what female Orlando is going to be like as a writer reaches its peak in the Victorian age, when we see a real push from society to change Orlando's androgynous ways. Orlando's left ring finger starts tingling from the need for a husband. But suddenly she needs a man to continue her writing. Without a husband, her hand keeps writing the most awful stuff, entirely without her control.
Orlando as she was (androgynous and free-thinking) just doesn't fit in the Victorian age. She needs something that makes her legible to an audience, and that something is a man. The Victorian age is demanding that Orlando become a "real woman." And will she?
Orlando winds up making compromises to her gender, and then publishes "The Oak Tree." It's at this stage of the book that we find a resolution both to the question, "What kind of a woman is Orlando going to be?" and "What kind of a writer is Orlando going to be?" In both cases, she's had to give a little to get a little.
As a woman, Orlando has submitted to the customs of the Victorian age: she has taken a husband and has had a baby (which happens in one paragraph [6.52] and is never referred to again, so he's easy to miss). However, she's still cheating a bit – this marriage isn't a formal, socially appropriate kind of marriage. She loves Shel, and besides, he's hardly ever around − leaving her free to love other people. So she gets married, but the marriage is on her own terms.
Orlando's marriage to Shel also works as an analogy to the compromise writing has to be between a public voice and private thoughts. Woolf doesn't seem to have much faith in the ability of language to communicate exactly what we think and feel. All writing can ever do is approximate what we think and feel. Orlando's marriage might represent the way she finds her public voice:
And [Orlando] heaved a deep sigh of relief, as, indeed, well she might, for the transaction between a writer and the spirit of the age is one of infinite delicacy, and upon a nice arrangement between the two the whole fortune of his works depend. Orlando had so ordered it that she was in an extremely happy position; she need neither fight her age, nor submit to it; she was of it, yet remained herself. Now, therefore, she could write, and write she did. (6.9)
So, just as Orlando merges the social contract of marriage with her own genuine feeling for Shel, she also negotiates between literary forms of the day and her own internal reflections. Her writing and her marriage are both a little bit society, a little bit herself.
As a result of this successful compromise, it's almost inevitable that she gets published, which is perhaps why she meets Nick Greene on the street. The text has taken on a life of its own, and that's the end of Orlando's struggle with language.
Except, of course, that it's never that simple. It's not as though Orlando died with the publication of "The Oak Tree." She is still here. How is this novel going to end? One of the problems that Woolf addresses in Orlando is how to work truth into fiction. Once "The Oak Tree," which had been the container for Orlando's hopes and dreams until now, is gone from the text, there are no more obstacles to exploring Orlando's innermost reflections. The final pages of Orlando conclude with an effort to get inside what was initially contained in "The Oak Tree": how Orlando really feels. (For more on this, see "What's Up With the Ending?")