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Ashley O'Mara is a native of Central New York. She was homeschooled and captained the North Area Loving Education at Home (LEAH) team on "Double Down," WCNY's high-school academic trivia game show. She attended SUNY Onondaga Community College before transferring to Le Moyne College, a Jesuit institution in Syracuse, NY, where she graduated summa cum laude with a BA in English and departmental honors in Creative Writing. She worked as a tutor at Onondaga Community College before completing an MA in English at Syracuse University, where she has taught composition and English literature classes. As of 2018, she is a PhD candidate at Syracuse University. In July 2017, she auditioned for Jeopardy in New York City, and on December 12, 2017, she competed on the show. Her episode aired on March 12, 2018.