She still credits her third-grade teacher, Virginia Davis, at Waite Phillips Elementary School, by praising her skill at writing.

[1] Several episodes she penned—namely, Sex and the City's "Evolution", "Attack of the 5'10" Woman", "Just Say Yes", "Plus One is the Loneliest Number", "I Love a Charade", and "Splat!

Her second book, a comic memoir about marriage entitled The Longest Date: Life as a Wife, was published by Viking in January 2014.

She has also written humorous essays for The New York Times, Real Simple, Harper's Bazaar, People, Allure, Slate, and Glamour.

In April 2018, it was announced Chupack would make her directorial debut on Otherhood, with Patricia Arquette, Angela Bassett and Felicity Huffman starring.