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Gregory é filho de Adam Gregory I. Ele se formou em Oak Hills High School em 2006 e atualmente está matriculado na Northern Kentucky University.
Ele aparece como ex namorado de Ashley Tisdale no video clipe "It's Alright, It's OK". Em agosto de 2010, foi escalado para o casting da novela americana de Thomas Forrester na CBS chamada The Bold and the Beautiful.
Ele é modelo da Nous Models. Atualmente, está noive de sua melhor amiga e modelo Sheridan Nicole (anteriormente Sheridan Sperry).
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