There is a certain pleasure in rereading a favorite book, in experiencing again its pleasures and in finding new ones. It can be especially worthwhile to reread a book when one is in a different stage of life.
I first read Orlando in college. I enjoyed it and admired it, but I didn't get much out of it other than the story itself and the commentary on the limitations historically placed on women. Rereading it 30+ years later -- wiser and more experienced, with a more nuanced understanding of the messiness of life -- was a different experience entirely. For one thing, I don't think I appreciated just how funny it is. The satire of not just gender norms but poets, publishing, and British history and culture is sharp, sometimes brutally so. Woolf has a keen eye for absurdity, as befitting a gifted writer who not only struggled with gender and heteronormative expectations but also the deeply flawed people she loved and with her own mental health. In this way the novel is strikingly modern, even though it is almost one hundred years old.
It's a postmodern novel too, purporting to be a traditional biography of Orlando, with a narrator who refuses to record some events because they are allegedly too distressing for the reader (such as Orlando's transformation from male to female, or her pregnancy), but seemingly accepts without question her subject's centuries-long life. Woolf includes portraits of real-life aristocrats as illustrations of her fictional characters, adding an element of playfulness. Moreover, each section of the book corresponds to a particular time period of English history, with heightened descriptions to match. The Frost Fair of 1608 is depicted with a cold beauty and startling details, such as the woman sitting with a lapful of apples for sale frozen at the bottom of the Thames and perfectly visible through the crystal-clear ice. Victorian England, by contrast, is pervaded with damp, resulting in lush, overabundant growth; so of course this is when Orlando gets pregnant.
But most of all, this novel is a love letter to Woolf's friend and lover, Vita Sackville-West, who inspired the character Orlando. Without the benefit of Wikipedia to educate me about Woolf's life, and reading this on my own rather than with a professor who could point me in certain directions, I completely missed this the first time around. This knowledge makes for a poignant read, because Orlando is very much an idealized (but not perfect) version of Sackville-West, without her selfishness and unfaithfulness, who finds true love in Shelmerdine (who was once a woman, and who is as unconventional as Orlando is).
I'm so glad I reread this.