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Crosley graduated from Connecticut College in 2000 with a degree in creative writing.

Books

Crosley's collection of essays, I Was Told There'd Be Cake, was published by Riverhead Books on April 1, 2008 and became a New York Times bestseller. Since then, HBO has purchased the rights to her book. In 2008 the audio book of I Was Told There'd Be Cake was selected as one of The Best Audio Books Of The Year by Library Journal and was one of Amazon.com's Best Books of 2008. In 2009, I Was Told There'd Be Cake was a finalist for the Thurber Prize for American Humor. How Did You Get This Number, her second book of essays, was released on June 15, 2010.

Journalism

Her essays, interviews, fiction and criticism have appeared in The New York Times, The Guardian, The Irish Times, BlackBook magazine, The New York Observer, The Village Voice, Vice Magazine, Elle , Glamour, Vogue, W, Teen Vogue, Salon.com, GQ, Esquire, Playboy Magazine, Self, Maxim Magazine, Plenty Magazine, Page Six Magazine, Mirabella, and numerous other literary journals and websites, such as Lumina and Esopus.

From 2004 to 2006, Crosley was a regular contributor to The Village Voice. She was a contributing editor and humor columnist for BlackBook Magazine. She has also appeared on Fox News, Sirius Satellite Radio and is a frequent contributor to NPR's "All Things Considered."