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Day was born in New York City, New York. His mother, Mary (née Peckham), is a piano teacher at The Pennfield School, in Portsmouth, Rhode Island, and his father, Thomas Charles Day, is an English/Music professor at Salve Regina University in Newport, RI. Day spent most of his childhood in Middletown, Rhode Island, attended The Pennfield School and graduated from Portsmouth Abbey School, both in Portsmouth. Afterwards, he attended Merrimack College in Massachusetts, where he played baseball.