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Stephen Bailey was born in South Bend, Indiana. Growing up he took part in many theatrical productions and showed a talent and love for performing. He began doing plays at South Bend Civic Community theater and getting cast in as many films as possible. He even grabbed a small video camcorder and began making short films of his own. He enrolled in Indiana University South Bend and studied Theatre Arts. He dropped out at the beginning of his junior year and began pursuing acting full time in Indiana and Chicago. He took a brief time off to study acting and became a ballroom dance instructor. He left the dance studio in 2011 when he booked a featured dancing spot on NBC's The Playboy Club and shortly after moved to Hollywood, California. In 2012 he became a co-owner of Unlimited Destiny Production, a small production company.