If Orlando’s transformation—from a young nobleman wooing Sasha on the frozen Thames to a woman navigating legal hurdles over property and title—hooked you, you’ll love how The Left Hand of Darkness reimagines gender entirely. On Gethen, people shift sexes; Genly Ai’s evolving bond with Estraven, especially during their perilous trek across the Gobrin Ice, mirrors the way Orlando’s life reframes intimacy, power, and selfhood across eras.

If you relished Orlando gliding from Queen Elizabeth I’s favor through the Great Frost fair and into the motorcars of 1928, The Bone Clocks offers a similarly time-spanning tapestry. Holly Sykes’s decades-long journey intersects with secret orders of near-immortals; like Orlando’s enduring pursuit of finishing “The Oak Tree,” Holly’s path reveals how private choices echo across eras touched by the uncanny.

If the biographer in Orlando made you grin—quibbling over ‘facts,’ indulging in lists, and winking at the reader while recounting the Archduchess Harriet’s surprise reveal as Archduke Harry—then Sterne’s Tristram Shandy will delight you. Tristram can’t keep his own story straight, detouring through digressions, typographical jokes, and self-contradictions that parody the very idea of a “faithful” life story.

If you enjoyed how Orlando’s narrator steps in to fuss over sources, chaptering, and truth—turning the biography inside out—Calvino’s If on a winter’s night a traveler doubles down. Addressing you as “Reader,” it spins a nesting-doll of beginnings that, like Orlando’s shape-shifting life and the coy handling of “The Oak Tree,” makes the act of reading itself the central adventure.

If the opulent sentences of Orlando—its rhapsodies over the oak, the seasons, and London’s metamorphoses—swept you along, Nightwood offers equally sumptuous prose. Through Robin Vote’s mercurial allure and Dr. Matthew O’Connor’s hypnotic monologues, Barnes crafts a modernist fever-dream of love and identity that echoes Orlando’s sensuous language and fascination with gender’s shifting edges.