By 1928, Virginia Woolf had established herself as a leading novelist experimenting with both form and content.  Rejecting Victorian plots that were linear explorations of characters’ lives, Woolf had published Mrs. Dalloway in 1925 and To the Lighthouse in 1927.  Both of these instant masterpieces utilized what would become known as “stream-of-consciousness,” a literary technique that insisted that our lives and thoughts do not proceed from year to year but rather jump around from past to present and even into future time.  Perhaps she was exhausted from the effort it had taken to break so completely from the traditional ideas of novels, so she sought release in fantasy, for surely Orlando, her next creative achievement, was seen as pure fantasy.  The title character begins life as a most definite “he” as we learn in the opening words of the novel:  “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.”  The “time” in question here is the late 16th century in England:  Elizabeth I has been on the throne a long time though Orlando is only seventeen as the story begins.  His swash-buckling behavior is inherited, since the Moor’s head was severed from its dark brown body by Orlando’s father (or perhaps grand-father as our narrator tells us, giving us a clue at the outset that time will not be calculated in the usual fashion in this novel).  That ancestor was in Africa fighting “barbarians” in his undoubtedly racist understanding of the black inhabitants of that continent.  The adolescent Orlando catches the aging Queen’s eye and so begins a remarkably fast-moving life of courtly service and love-sick fascination with a young Russian girl whom he sees skating on a frozen pond.  Woolf wants us to understand the force of gender roles in her own world in writing about this scene because she says “When the boy, for alas, a boy it must be–no woman could skate with such speed and vigour–swept almost on tiptoe past him, Orlando was ready to tear his hair with vexation tha the person was of his own sex, and thus all embraces were out of the question.”  But Woolf is all about gender confusion in this romping tale, so she continues the scene this way:  “Legs, hands, carriage, were a boy’s but no boy ever had a mouth like that; no boy had those breasts; no boy had those eyes which looked as if they had been fished from the bottom of the sea.”  Then this tantalizing skater stops and Orlando sees the truth:  “She was a woman” with whom he can safely fall in love, so he does.

For Woolf’s own audience in 1928, this kind of playfulness about gender identification and presentation surely came as something of a shock.  Reviews of the book didn’t know quite what to make of it.  Reviewers had expected another novel in the same serious experimental vein of Mrs. Dalloway or To the Lighthouse, though many reviewers of these novels hadn’t known what to make of them either.  But the grounds of confusion in the previous cases were solid because they concerned narrative method; here this burgeoning woman novelist was presenting a world in which sex and gender were slippery and elusive.  As Orlando moves through the 17th century, he matures into a handsome young man about town who keeps having feelings that don’t “fit” with his outward presentation.  Then, about a fourth of the way into the story, the young handsome lad falls strangely ill into trance that lasts over a week.  As doctors try to determine the cause of his malady, Orlando is visited by three female voices who perform a typical 17th century masque.  The actors speaking to our hero lost in his deep sleep are our Lady of Purity, our Lady of Chastity, and our Lady of Modesty.  After each delivers her words about how life in England has no more room for them, some trumpeters who have announced each of their appearances to the sleeping Orlando “blow one terrific blast” and our narrator proclaims “THE TRUTH!”  Orlando suddenly wakes and we read “He stretched himself.  He rose.  He stood upright in complete nakedness before us, and while the trumpets pealed Truth!  Truth! we have no choice left but confess–he was a woman.”  Surely there is no way to understand this amazing scene if we read it in 2018 except to say that Virginia Woolf is presaging a world in which a person of one anatomical sex can undergo a radical transformation into another anatomical sex.  

That she could presage our own trans moment shouldn’t come as such a shock if we look at certain details of her own life.  Her most serious intimate relationship surely was with Vita Sackville-West, the aristocratic woman with whom Virginia was in love and with whom she spent long and happy periods of her life, never mind that both had husbands.  Vita liked nothing more than to dress as a tall handsome man and on more than one occasion, she and Virginia attended plays and concerts as a heterosexual couple.  Woolf writes of one such escapade, sharing her delight at having fooled an older heterosexual couple who actually knew both women but didn’t recognize Vita in her male disguise.  In various essays, Woolf would explore “androgyny,” asserting that all humans combine in ourselves certain aspects of what society labels “masculine” and “feminine” traits, and that the most interesting of us are those who inhabit both worlds.  So in her putative fantasy novel, she creates a single human being who lives from the late 16th century until October 11, 1928, the date registered in the last words of this romping story of Orlando who is boy/man until that no longer “works,” so “he” becomes needs to become “she” in order to express some “truth” that has played around the edges from those opening scenes full of gender confusion.

Once Orlando becomes a woman, she has adventures beginning with running away to live with a group of Romany people until they help her understand she has to return to her own world.  She is able to adapt to the centuries until she got to 19th c.  Conformity to what a young woman was supposed to be wore her spirit down because she’d always been able to stand against the norm and still be accepted.  The most oppressive aspect of her culture at that time was the pressure to find a heterosexual mate and stop being single as Orlando had chosen to remain for a few hundred years.  But the universe turns towards her and as she is roaming in Turkey, a man on a horse approaches her because he thinks she is a damsel in distress.  Sensing her distress, the stranger leaps from his large horse and declares “Madam, you’re hurt.!”  Orlando’s reply is “Sir, I’m dead!”  Woolf collapses time and engagement with her next sentence:  “A few minutes later, they became engaged.”   This magical man’s name is Marmaduke Bonthrop Shelmerdine, Esquire–“Shel” for short.  Just as they are pledging eternal love, both sense the deep truth of the matter–“You’re a woman, Shel!:  she cried.  “You’re a man, Orlando!” he cried.  This grasp of the trans nature of each half of this strange equation solves all their dilemmas and they live happily ever after–until they come to the present moment (1928).   As Woolf so wisely writes  “For what more terrifying revelation can there be than that it is the present moment?”  Orlando stops her whirligig life to consider who she really is in that present moment and concludes that each of us is composed of multiple selves–“some say two thousand and fifty-two”–and her job after all the centuries s/he has lived is to.  Woolf, in an act of authorial comfort, lets her character experience a unifying moment when s/he feels s/he is a true self.  As this fabulous tale ends, Orlando keeps having very old memories both of when she presented as a young man and when she tried to live as a maturing woman.  The last thing s/he sees is “her husband’s brig, rising to the top of the wave!  Up it went! and up and up.  Oh rash, oh ridiculous man, always sailing, so uselessly, round Cape Horn in the teeth of a gale!  But the brig was through the arch and out on the other side; it was safe at last!”  S/he sees Shel coming towards her/him in all his/her glory and she shouts out so Shel will see where s/he is.  They meet as a single wild goose flies over them and the curtain falls on this very early experiment in trying to escape gender binaries.  

Rereading this amazing novel that Woolf calls a “biography,” I feel excited to discover again just how prescient she was about human existence in all its profound and mysterious aspects.  And, who knows, she may see it as a life story not only of Orlando but of her own complicated relationship with Vita Sackville-West.  Surely it is no accident that she dedicates the novel “To V. Sackville-West” who loved every minute of the tale as she told Virginia in a letter after having read an early draft.  And surely both of them understood, perhaps nonverbally, what it means to feel fluidity rather than certainty about gender identity.