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Virginia Woolf wrote Orlando: A Biography in 1928, following the publication of acclaimed novels Mrs. Dalloway and To the Lighthouse. Orlando is dedicated to her friend and lover Vita Sackville-West, and fictionalizes the Sackville family history and Sackville-West's own flexible approach to sexuality and marriage. Orlando also works as an enactment of Woolf's prescription to biographers, in her 1927 essay, "The Art of Fiction" and "The New Biography," to "yoke truth with imagination" (source). Woolf argues for increased truth in fiction and increased fiction in truth. In other words, she seems to be arguing for a novelistic approach to biography. (For more on this, check out Orlando's "Character Analysis.")
Orlando has been popularly read as an example of lesbian or bisexual fiction. While Vita Sackville-West's son and biographer confirms that Woolf was writing about Sackville-West's sexual adventures with both genders, the fantastical trappings of the story (the gender switching, voyages abroad, etc.) meant that the censors of the day wouldn't necessarily have noticed the risqué content. Furthermore, the book has often been dismissed as a less serious work than Woolf's previous novels. However, we find the novel 1) awesome, and 2) about so much more than ambiguous and shifting sexualities. Nothing is solid in this novel, not history, writing, or even character names. It's explosively experimental, and gender roles are just one of its many targets.
It's one of the first lessons modern society teaches us: There are boys and girls, and you are one or the other. If you're a girl, your parents are supposed to dress you in pink, and if you're a boy, your parents are supposed to dress you in blue.
Of course, that wasn't always the case. (Bonus points if you knew that already.) In fact, until the Baby Boomers came along in the 1940s, pink was considered the more masculine color and light blue was associated with the feminine. And that's kind of the point—all of these rules and expectations about gender are arbitrary.
We all come to realize that these categories aren't hard and fast, and thanks to LGBTQIA+ people on social media and in the public eye, younger generations are pushing back against that gender binary. But still, some people insist that there is some biological basis for thinking that women are different from men. You've heard the stereotypes: Women are more nurturing; men are more aggressive, yada yada.
Orlando would say to this biology business: No. Or maybe the novel would argue that our private parts influence our public behavior because of those societal expectations, but in a perfect world, they wouldn't.
What we have here is a fabulous fantasy of what life could be like with a more fluid approach. Orlando has been both a man and a woman, and so Orlando understands the nature of her former lovers (especially Sasha) and present husband, Shel. What Orlando learns would have been hidden from her if she couldn't move between bodies and genders.
Orlando uses gender to imagine what it would be like if our social identities were less bound to our bodies. Would there be gender hierarchies in our society if we could really experience how the other half lives?
Orlando is making an argument for the power of imagination: Sure, we're all bound to our own bodies, and we won't be lucky enough to live 400 hundred years, like Orlando does. But we all have the capacity to empathize with others in the pursuit of deeper truths about the human experience, unbounded by gender, race, and place. These physical factors can't be done away with, and Woolf keeps coming back to Orlando's biology as a recognition that you can't always ignore your body. But you can use your imagination (possibly in conjunction with a good book) to try on someone else's experiences for a day.
Orlando stars Tilda Swinton in the title role and Billy Zane as Shel
The 1992 movie trailer with Tilda Swinton as Orlando.
Love at First Sight
The clip from the movie when Orlando and Shelmerdine meet.
An image of Woolf as an older woman.
Virginia Woolf Society of Great Britain
This organization creates a publication with writings on Virginia Woolf and her works. Under "Resources," there are also cool links, like pictures of all of Woolf’s gorgeous houses in the countryside and other interesting tidbits.
The International Virginia Woolf Society
This website isn’t very attractive, but it has a helpful "Links" section.
The real biography of Vita Sackville-West. Notice some similarities between her and Orlando?