We first meet Orlando around 1586, age 16:

He--for there could be no doubt of his sex, though the fashion of the time did something to disguise it--was in the act of slicing at the head of a Moor which swung from the rafters. It was the colour of an old football, and more or less the shape of one, save for the sunken cheeks and a strand or two of coarse, dry hair, like the hair on a coconut. Orlando's father, or perhaps his grandfather, had struck it from the shoulders of a vast Pagan who had started up under the moon in the barbarian fields of Africa; and now it swung, gently, perpetually, in the breeze which never ceased blowing through the attic rooms of the gigantic house of the lord who had slain him.

By the end of the book, Orlando will be 36, a woman, and the year will be 1928. This wonderfully odd, oddly wonderful "biography" follows Orlando and their writing career, along with the progression of English literature and society, through all the changes between, before collapsing in on itself a bit at the end. (Despite the weirdness at the end, I'm rating this five stars, because I found most of it absolutely delightful.) Written for Woolf's lover, [a:Vita Sackville-West|3904620|Vita Sackville-West|https://images.gr-assets.com/authors/1417920269p2/3904620.jpg], the fun she had in fictionalizing her friend and satirizing her country shines through.

Although it's often been billed as a book about one person who lives for hundreds of years, time is fluid for several characters throughout the novel, including a chaplain, a writer turned critic, and a gender-bending Roumanian in hot pursuit of Orlando. This novel gets surreal in many ways and I was there for most of it.

I'm going to mark the rest of this as spoilers, because I provide a general outline of the novel, but really it's A LOT of extended quotes, because I wanted to share all the things. (And I feel like the basic plot of this book is general knowledge.)


At sixteen: Soon he had covered ten pages and more with poetry. He was fluent, evidently, but he was abstract. Vice, Crime, Misery were the personages of his drama; there were Kings and Queens of impossible territories; horrid plots confounded them; noble sentiments suffused them; there was never a word said as he himself would have said it, but all was turned with a fluency and sweetness which, considering his age...were remarkable enough.

It's at this age that Orlando innocently charms his cousin, Queen Elizabeth, who signs over "the great monastic house that had been the Archbishop's and then the King's to Orlando's father." (Apparently in the movie adaptation, Elizabeth promises Orlando the house will be his forever if he stays eternally youthful: "Do not fade. Do not wither. Do not grow old." Nothing so direct occurs in the book.)

At any rate, two years of this quiet country life had not passed, and Orlando had written no more perhaps than twenty tragedies and a dozen histories and a score of sonnets when a message came that he was to attend to the Queen at Whitehall.

She gives him a ring from her finger and names him "her Treasurer and Steward."

He was to be the son of her old age; the limb of her infirmity; the oak tree on which she leant her degradation. She croaked out these promises and strange domineering tendernesses (they were at Richmond now) sitting bolt upright in her stiff brocades by the fire which, however high they piled it, never kept her warm.

But when she spies him kissing a girl, it pretty much kills her (which would put us around 1603, but Orlando is still a youth).

It was Orlando's fault perhaps; yet, after all, are we to blame him? The age was the Elizabethan; their morals were not ours; nor their poets; nor their climate; nor their vegetables even. Everything was different. The weather itself, the heat and the cold of summer and winter, was, we may believe, of another temper altogether. The brilliant amorous day was divided as sheerly from the night as land from water. Sunsets were redder and more intense; dawns were whiter and more auroral. Of our crepuscular half-lights and lingering twilights they knew nothing. The rain fell vehemently, or not at all. The sun blazed or there was darkness. (Woolf goes on for a while, but I'll stop and leave you to read the rest for yourself if you find this all as amusing as I do.) As for the girl, we know no more than Queen Elizabeth herself did what her name was. It may have been Doris, Chloris, Delia, or Diana, for he made rhymes to them all in turn; equally, she may have been a court lady or some serving maid. For Orlando's taste was broad; he was no lover of garden flowers only; the wild and the weeds even had always a fascination for him.

Over the next years, Orlando continues his romantic escapades, first with lower class women and then with potential wives of his own class, until the (first) Great Frost of 1607-08 when he meets a Russian princess who is stranded in London when the Thames freezes. In the opulent setting of King James's first Frost Fair, Orlando falls desperately in love with the princess, who he first mistakes for a boy when he sees her skating on the river. Chapter One ends with her abandoning him as the Thames thaws, an event from which Orlando never fully recovers.

Exiled from London society for his scandalous behavior with "the Muscovite" and accompanying abandonment of his former fiancée, the Lady Margaret, Orlando returns to his estate. That summer, there's a strange incident where he sleeps for seven days straight, not responding to any of the increasingly extreme attempts to wake him. When he wakes, he acts as if nothing had happened. He proceeds to live in relative solitude, communing with the bones of his ancestors in the family crypt. At this time (approximately 1608), the housekeeper, Mrs. Grimsditch, and the chaplain, Mr. Dupper, are introduced, along with other household staff, who worry about their master's odd behavior.

A fine gentleman like that, they said, had no need of books. Let him leave books, they said, to the palsied or the dying. But worse was to come. For once the disease of reading has laid hold upon the system it weakens it so that it falls prey to that other scourge which dwells in the ink pot and festers in the quill. The wretch takes to writing.

More years pass, until Orlando decides to seek out a famous writer of the time named Sir Nicholas Greene, who agrees to come for a visit. Mr. Greene is a bit disappointing: physically unattractive, prone to complaining about his own health, and disdainful of other writers Orlando admires: Shakespeare, Marlowe, Ben Jonson, Browne, Donne.

Now all young writers were in the pay of the booksellers and poured out any trash that would sell. Shakespeare was the chief offender in this way and Shakespeare was already paying the penalty. Their own age, he said, was marked by precious conceits and wild experiments--neither of which the Greeks would have tolerated for a moment. Much though it hurt him to say it--for he loved literature as he loved his life--he could see no good in the present and had no hope of the future. Here he poured himself out another glass of wine.

After convincing Orlando to give him an annual pension so that he won't be beholden to "the booksellers," Nick Greene departs, taking with him Orlando's play, the Death of Hercules. He turns around and writes a satirical poem roasting Orlando and his literary ambitions. Orlando responds by declaring, "I have done with men," buying Norwegian elk hounds for companionship, and burning everything he's ever written, except a poem called "The Oak Tree." (The biographer tells us that Orlando is now "the age of thirty, or thereabouts.")

More years pass, until Orlando decides he will only write for himself from here on out. He spruces up the house and reenters society, continuing to work on "The Oak Tree, A Poem." The persistent attentions of a very unusual suitor, "Archduchess Harriet Griselda of Finster-Aarhorn and Scadaop-Boom in the Roumanian territory," eventually disrupt his pleasant life.

Thus realising that his home was uninhabitable, and that steps must be taken to end the matter instantly, he did what any other young man would have done in his place, and asked King Charles to send him as Ambassador Extraordinary to Constantinople. The King was walking in Whitehall. Nell Gwyn was on his arm. She was pelting him with hazel nuts. 'Twas a thousand pities, that amorous lady sighed, that such a pair of legs should leave the country. Howbeit, the Fates were hard; she could do no more than toss one kiss over her shoulder before Orlando sailed. (Thus ends Chapter 2. King Charles & Nell Gwyn's cameo would place this in the 1670s.)

It is in Constantinople, that Orlando eventually goes into another long slumber, apparently after having married a dancer named Rosina Pepita. He conveniently sleeps through riots in which "The Turks rose against the Sultan, set fire to the town, and put every foreigner they could find, either to the sword or to the bastinado." (The rioters think he's already dead and simply steal his coronet and robes.) Upon waking:

Orlando had become a woman--there is no denying it. But in every other respect, Orlando remained precisely as he had been. The change of sex, though it altered their future, did nothing whatever to alter their identity. Their faces remained, as their portraits prove, practically the same.

Orlando escapes with "an old Gipsy" and lives with the "gipsy tribe" until cultural differences drive her back to England. (They're not impressed that she owns a house with 365 room and 52 staircases, and nature doesn't make them want to write poetry.) Upon returning to England, she learns that Addison, Dryden, and Pope are the literary giants of the day, which would make this the early 18th century. (Despite almost 100 years having passed since they were first mentioned, Mrs. Grimsditch and Mr. Dupper are still around. Also, one of Orlando's elkhounds recognizes her, despite approximately 30 years having passed since she left the country.)

No sooner had she returned to her home...than she was made aware...that she was a party to three major suits which had been preferred against her during her absence... The chief charges against her were (1) that she was dead, and therefore could not hold any property whatsoever; (2) that she was a woman, which amounts to much the same thing; (3) that she was an English Duke who had married one Rosina Pepita, a dancer; and had had by her three sons, which sons now declaring that their father was deceased, claimed that all his property descended to them.

Not only that, but the Archduchess Harriet Griselda is still around (yikes!) and is actually Archduke Harry (double yikes!) who only pretended to be a woman because Orlando was a man back then. She finally manages to get rid of him, hobnobs with Addison, Pope, and Swift (who turn out to be fairly normal dudes). Life goes on, until Orlando accidently "let the sugar fall with a great plop" into Mr. Pope's tea.

Never was any mortal so ready to suspect an insult or so quick to avenge one as Mr. Pope. He turned to Orlando and presented her instantly with the rough draught of a certain famous line in the "Characters of Women." Much polish was afterwards bestowed on it, but even in the original it was striking enough. Orlando received it with a curtsey. Mr. Pope left her with a bow. Orlando, to cool her cheeks, for really she felt as if the little man had struck her, strolled in the nut grove at the bottom of the garden. Soon the cool breezes did their work. To her amazement she found that she was hugely relieved to find herself alone.

She passes the rest of the 18th century in the company of common women and doing what she pleases. The biographer says it's difficult to find any definitive information about Orlando from this period.

She had, it seems, no difficulty in sustaining the different parts, for her sex changed far more frequently than those who have worn only one set of clothing can conceive; nor can there be any doubt that she reaped a twofold harvest by this device; the pleasures of life were increased and its experiences multiplied. From the probity of breeches she turned to the seductiveness of petticoats and enjoyed the love of both sexes equally.

Chapter Five opens with the 19th century and Woolf's take down of the Victorian era. I've already quoted far too much, but her description of the damp, dismal gloom of that era is epic. Orlando feels increasing pressure as a single woman and, conveniently, finds a gender-nonconforming adventurer out on the moors, by the name of Marmaduke Bonthrop Shelmerdine, Esquire. They're perfect for each other, especially the fact that he's always away at sea. Old Mr. Dupper (the chaplain) marries them (approximately 200 years after he was introduced), and just in time, as Orlando has been declared a woman by the courts, and therefore unable to own property.

Finally turning her attention back to "The Oak Tree," Orlando finishes up the poem she's been working on for nearly 300 years. She catches a train (her first) to Charing Cross station (making this at least 1864) because the poem wants to go to London. There she runs into "her old, her very old friend, Nick Greene!" (Yes, he of the scathing satire.) He's come up in the world, having become a knight, a professor, and "the most influential critic of the Victorian age." Of course, his tastes in literature have completely changed:

"Ah! my dear lady, the great days of literature are over. Marlowe, Shakespeare, Ben Jonson--those were the giants. Dryden, Pope, Addison--those were the heroes. All, all are dead now. And whom have they left us? Tennyson, Browning, Carlyle!"--he threw an immense amount of scorn into his voice. "The truth of it is," he said, pouring himself a glass of wine, "that all our young writers are in the pay of the booksellers. They turn out any trash that serves to pay their tailor's bills. It is an age," he said, helping himself to hors d'oeuvres, "marked by precious conceits and wild experiments--none of which the Elizabethans would have tolerated for an instant."

The more things change, the more they stay the same.

"The Oak Tree" happens to fall out of Orlando's bodice and Sir Nicholas declares it delightful and promises to use his connections to get it published. Discovering that books are now cheap and plentiful, Orlando buys a copy of everything she can find. Having finally brought her literary child out into the world, she births a human child, too: a boy who can inherit the familial home.

King Edward ascends the throne and suddenly the sun comes out again, conveniently accompanied by electric light that brings the city out of darkness and into the "modern" age. As I said before, it all gets a little weird from there, with Orlando reflecting on 350 years of life crammed into 36 biological years. Her husband comes flying in via aeroplane along with the "wild goose" of literary success that she's been chasing throughout the novel. And it all ends with the exact day that Woolf's novel was originally published.

If you've made it this far despite not having read this novel (or even if you skipped all my "spoilers," which are mostly just excessive quotes), do it. This book is weird and wonderful, just like Virginia Woolf. ( )

The story of Orlando spans over 300 years (1588–1928). During this time, Orlando ages only thirty-six years, and changes gender from a man to a woman.

Orlando is not an easy read. Some of the jokes have gone a bit stale. But its quality has stood the test of time.

Orlando is a reminder – if one were needed – that alternative life-styles, counter-normative sexuality and literary provocateurs existed long before the third decade of the twenty-first century. ( )

This is a book best read after you're 40. If you were forced to read this in college then I fully understand why this book made no sense to you whatsoever. Quite frankly I don't quite get it completely myself yet but I do appreciate its scope and intent. In a nutshell Orlando, a titled squire a few centuries ago can't find peace of mind and eternally asks the question: is this all there is? Through many abstract adventures and many decades of living he lands in Italy where he falls asleep for days only to awake a woman. From this perspective and this point on a similar story is told and Orlando still asks the question: now that I have this different perspective: does it matter?

None of the questions stated above can be explicitly found in the novel. In fact nothing I said so far is really clearly described and if someone argued that the entire book is the retelling of a dream I might agree. Many passages appear to be randomly stitched together and certain facts which appear crucial are even casually mentioned and then dropped altogether (such as Orlando having a son). There is a reason for this I'm convinced.

It is a short book written in archaic language that changes depending on the time period Orlando lives in. That makes the book difficult to read if the vagueness and dreamlike sequences weren't throwing you off in the first place. Reading Orlando is a lot easier of you've first read All Men Are Mortal by Simone de Beauvoir. That particular novel asks the same question and wants to know what this life we live is all about. But it does so by playing a man and a woman against each other so that we see our existence through their conflicts. In Orlando this idea is compressed by literally combining the two sexes into one.

Virginia Woolf left out a lot of narrative detail because it isn't important for the question she asks. That is why we do not know how it happens that Orlando changes from a man into a woman. Or why nobody thought it weird that the owner of the mansion suddenly appeared quite different.

Although Woolf goes into some detail regarding human relationships, she paints Orlando as someone intrigued by that part of humanity but who isn't completely invested in it. It is difficult to say what the author wanted Orlando to conclude about human existence but it seems she concludes that art and writing is the only valuable activity and product we can experience and produce in our lifetime.

Then again I might have to read it again in about 20 years to see if my perspective has changed yet again about this novel. ( )

Beautiful. Breathtaking. ( )

Here's what I wrote in 2015 about this read: "Orlando begins as a male and lives about 500 years in England/London and magically becomes a woman along the way. Good fun, good read, and lots of comments on the boundaries faced by women (starting with restrictive clothing). Apparently, Orlando was inspired by Wolff's female lover." Quotations in the comments section are my exact kindle highlights. ( )