I thought I hated Orlando. I took a Gay and Lesbian Lit class in college, and the professor assigned it. I think I got through about a third of it and quit because I thought it was crap. I think the problem was that I didn't think I'd like Virginia Woolf and didn't want to give her a chance. But, then again, my literary tastes were weird: the same professor assigned The Well of Loneliness by Radclyffe Hall, and I loved it. No one likes that novel. I didn't know what I was missing in Orlando (or Virginia Woolf, for that matter).
Here's the gist: Orlando is a young English aristocrat who has a very adventurous life. He doesn't really age (like other random characters in the novel), and he lives through several centuries. At some point, he finds himself an ambassador a long way from home. He wakes up one morning, and discovers that he's turned into a woman. Then she goes back to England and spends the rest of her life as a woman.
As much as I thought I hated this novel when I was in college, I loved it now. I loved every minute of reading it. It was hours and hours of joy. I'm pretty sure that Orlando is my new favorite Virginia Woolf novel. The others that I've read (I've read quite a few) aren't much like this one – for that matter, there aren't many novels like this one. The message, here, is that though there are differences between the sexes, Orlando remained essentially the same person, whether male or female. Which goes along with “A Room of One's Own,” and the like. I'm still not sure why I was so convinced that I'd hate it. I almost want to read it again right now.