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Sean Cunningham has a diverse work experience that spans several industries. In 2001, they started working as a writer, contributing to various publications such as the Wall Street Journal, CNN, Men's Journal, Esquire, and more. Sean also worked as a freelance writer and editor for Rep Cap, InsideHook, Maxim, and other companies from 2005 to 2022. In 2007, they freelanced as a writer and editor for The Knot until 2009. Later in 2009, they briefly worked as a writer for AMCTV.com. Most recently, in 2022, they joined Plan A Technologies as the Director of Communications.

Sean Cunningham has an A.B. degree from Princeton University and an MFA degree from Yale University. There is no specific information available regarding the start or end years of their education at either institution.