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Orlando: A Biography is a fictional biography by Virginia Woolf. The novel follows Orlando, who starts out as a young nobleman during the reign of Queen Elizabeth I, and follows his love affair with a Russian princess, his ambassadorship in the East, and his spontaneous sex-change and life afterward as a woman. Despite living from the 16th through the 20th centuries, Orlando is 36 when the novel ends in the present day (well, October 11, 1928, but that was the present when it was written). The various themes of the novel, including gender, literature and poetry, and the passage of time, are explored by Orlando's experiences with these subjects. Being mainly known for being a story of gender-bending, Orlando covers many Gender Blending Tropes. The novel was supposedly written by Woolf as a love letter to her lesbian lover Vita Sackville-West. Orlando was made into a movie starring Tilda Swinton in 1992, and adapted into a play by Sarah Ruhl in 2010.

Orlando: A Biography contains examples of following tropes:

  • Abhorrent Admirer: Archduke Harry
  • Anthropomorphic Personifications: Purity, Chastity, and Modesty. See the entry for Big Lipped Alligator Moment on the YMMV page.
  • Attractive Bent Gender: Orlando was already good-looking as a man; upon transformation, Lady Orlando's body is said to have the best-looking aspects of either gender.
  • Gender Bender: One of the earliest in literature; anything older is usually covered by mythology instead, like Tiresias of Greek Mythology.
  • Getting Crap Past the Radar: Depictions of bisexuality in fiction were illegal in Britain at the time, so Woolf gets around this by having her character switch sexes midway through the novel.
  • Hide Your Gays: Archduke Harry originally tries to woo the male Orlando disguised as a woman, but drops the disguise after Orlando becomes a woman.
  • Jumping the Gender Barrier: Orlando is a playboy only interested in women when he is a man, and then shows only interest in men when he becomes a woman.
    • Well, there were Nell and her friends, whom Orlando remembers quite fondly afterwards (though she might noght have sex with any of them, she clearly was attracted to Nell). And though she managed to convince "spirit of the age" that it's okay for a woman to compare flowers to Egyptian girls in her poetry as long as she has a husband, a narrator notices that "she had only escaped by the skin of her teeth" there.
  • Just Woke Up That Way: How Orlando turned into a woman.
  • Man, I Feel Like a Woman: subverted
  • Mother Russia Makes You Strong: Discussed with Sasha.
  • Padding: To quote,

  It was now November. After November, comes December. Then January, February, March, and April. After April comes May. June, July, August follow. Next is September. Then October, and so, behold, here we are back at November again, with a whole year accomplished.

    • Although it makes sense in context, all is vanity, it does seem like Woolf is running out of ideas nearing the end.
  • True Art Is Ancient: An In-Universe example. To Nicholas Green, who also lives for centuries longer than he should, the greatest art is always that of about five hundred years ago.
  • Second Law of Gender Bending: Succinctly summarized by the protagonist:

 Orlando: Praise god I'm a woman!

  • Unusually Uninteresting Sight: Everyone treats Orlando's eternal youth and gender changes as totally unremarkable, including Orlando him/herself.
  • Victoria's Secret Compartment: Over the years, Orlando keeps her manuscript of "The Oak Tree" in her bosom. Probably in more of a secluded pocket than right next to her skin, but still...
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