by Virginia Woolf
Difficulty: Hard
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Here’s a summary of Orlando: a lonely young man with nice legs (very nice, we are repeatedly assured) gets dumped by a Russian princess after their ice river carnival was swept away in a sudden thaw. He’s sad for a while, and decides to go abroad as a royal ambassador. Then one night, in a flurry of trumpets and Spensarian theatrics, Orlando transforms into a woman for some reason (who still has nice legs). And everyone’s cool with it, though she does need to go through a lengthy legal process to retain ownership of her property now that she’s a woman. So she returns to England, and spends time writing poetry and hosting famous poets at her estate. Eventually, Orlando wins her lawsuit for her property and decides to marry a sea captain named Marmaduke Bonthrop Shelmerdine (seriously). They then live happily ever after for at least several hundred years.

I love Orlando for how un-seriously it takes itself. There aren’t many ‘great English authors’ who were willing to let themselves have this much fun. Even when composing parodies or satires they’re always very serious about their art and their reputations, but perhaps Woolf cared less because she had other reasons for writing this novel. Orlando is often called the ‘longest love-letter in literature’ because it was written for Woolf’s close friend and sometimes lover Vita Sackville-West, represented by the character Orlando. In Virginia’s eyes, Vita transcended the limitations of gender, time, and place, so Orlando does too (she must have had very nice legs too, if the pattern holds). I find it incredibly romantic that one of the most radical and celebrated novels of the 20th century sprung from such a relationship. What a monument to the lover!

While Orlando is one of Woolf’s most accessible novels, it’s still written in dense, high-modernist fashion and may prove a bit difficult at times. Goofy as the plot can be, it’s not really a laugh-out-loud comedy though it does have its moments. It’s a bit difficult to say how the character Orlando would be labelled in our current moment. The concept of transgender didn’t really exist at the time, and Orlando continued to dress as both man and woman as it suited them, suggesting that neither their male or female version is more correct than the other. The obvious term might be ‘genderfluid,’ but Woolf had some slightly different ideas about the relationship between the masculine and feminine. In A Room Of One’s Own, she muses upon the necessity for the artist to be “man-womanly” or “woman-manly” in order to consider all points of view and achieve lasting art. I find this interesting to consider in our era of names and labels. What if, fifty years from now, we discover we’ve had this whole gender thing wrong the whole time? Or some other aspect of sex and sexuality that we treat as fact today? Orlando helps us think about those questions, and so it remains one of the more important LGBT+ books yet written.

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