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Flewelling grew up in northern Maine, United States, and has since lived on both coasts and traveled around the world, all experiences that are reflected in her writing. She has worked as a teacher, a house painter, a necropsy technician, and a free-lance editor and journalist. She has been married to Douglas Flewelling since 1981, and has two sons. She currently lives in Redlands, California, where she continues to write, and offers lectures and creative writing workshops at the University of Redlands. Flewelling is a convert to Thiền Buddhism, having taken her vows with Engaged Buddhist monk Thich Nhat Hanh, and is a practitioner of Buddhist meditation. Flewelling's writings promote feminism and LGBT causes, having said in relation to these topics, "I’ve always believed that people are people, and it’s wrong to discriminate against them just because of what gender or group they fall into."
Her first Nightrunner novel, Luck in the Shadows, was a Locus Magazine Editor's Pick for Best First Novel and a finalist for the Compton Crook Award. Her novels Traitor's Moon (2000) and Hidden Warrior (2004) were both finalists for the Spectrum Award. Her novels are currently published in 13 countries, and in 2005, the first volume of the Japanese language version of Luck in the Shadows was published. Ms. Flewelling is accessible to readers through her web site, her Live Journal blog, her Yahoo! group, and numerous guest appearances at conventions including Comic-Con and Smith College's ConBust. Her work has been praised by other notable fantasy authors, including George R. R. Martin,Orson Scott Card,Elizabeth Hand,Robin Hobb, and Katherine Kurtz. Independent film company Csquared Pictures has acquired film rights to the first three books in the Nightrunner series, but they have not yet started production.
Flewelling's work has frequently promoted LGBT themes as well as topics related to gender. The protagonists of the Nightrunner books are both bisexual, and Flewelling has stated their creation was in response to the near-absence of LGBT characters in the genre and marginalization of existing ones. The Tamir Triad, combining elements of psychological drama with ghost story horror, features a protagonist who transforms from one sex and gender to the other. Flewelling's works have drawn academic attention in relation to these themes.