Weisberger was born in Scranton, Pennsylvania to a school teacher mother and a department-store-president turned mortgage-broker father. Her family is Jewish and Weisberger was raised in Conservative Judaism and later Reform Judaism. She spent her early youth in Clarks Summit, Pennsylvania, a small town outside Scranton. At age eleven, her parents divorced and she and her younger sister, Dana, moved to Allentown, Pennsylvania, in the Lehigh Valley region of the state, with their mother.
In 1995, she graduated from South Whitehall Township's Parkland High School, near Allentown. During her time at Parkland, Weisberger was involved in various activities, including intramural sports, some competitive sports, extra projects, and organizations.
Following her graduation from Parkland High School, she attended Cornell University in Ithaca, New York, where she was an English major and a sorority member of Alpha Epsilon Phi, graduating in 1999. After college, she traveled as a backpacker through Europe, Israel, Egypt, Jordan, Thailand, India, Nepal, and Hong Kong. Returning home, she moved to Manhattan and was hired as Wintour's assistant at Vogue. She was there for ten months before leaving along with features editor Richard Story. While she herself said she felt out of place there, the magazine's managing editor, Laurie Jones, said "she seemed to be a perfectly happy, lovely woman".
After leaving the fashion magazine, she wrote 100-word reviews for Departures Magazine, an American Express publication, before writing her first novel. She also published an article in Playboy magazine in 2004.
Her success came really from her stint at Departures Magazine working as an assistant editor. After mentioning her interest in writing classes to her boss, Richard Story, he referred her to his long esteemed friend, Charles Salzberg. She started writing a story about her time at Vogue, trying to complete fifteen pages every couple of weeks. After continuous nudging for her to show her completed writing to agents, she finally did and within two weeks, it was sold.
Weisberger resides currently in New York City.