Virginia Woolfs Orlando (1928) and Jeanette Winterson's The Passion (1987), though separated by both fifty-nine years and the critical gulf of modernism and postmodemism, share many traits, not the least of which is a tendency to be taken less than seriously by readers and critics. An aura of lovely frivolity surrounds both novels, in some ways quite literally, as Nigel Nicolson's flattering yet reductive assessment of Orlando as "the longest and most charming love letter in literature" appears on the cover of many editions. The Passion bears its own scarlet letter-like summation, as its cover, courtesy of Edmund White, proclaims it to be a "fairy tale about passion, gambling, madness, and androgynous ecstasy." Despite these limiting labels, the literary tides have turned, slowly for Orlando, and more quickly for The Passion. Whereas Elizabeth Bowen once "regarded [Orlando] as a setback" (216) for Woolf, she came around enough to write an Afterword for the 1960 edition. Likewise, Winterson's further novels and critical essays have encouraged readers to dig more deeply into The Passion as both a postmodem and a feminist text. One of Winterson's essays argues explicitly on behalf of Orlando, suggesting potent links between these two writers, as well as a need to look a bit more closely at their love letters and fairy tales.