In 2003, Headley married Brian Musso, an investment advisor who briefly played for the New York Jets. Aftergraduate from Northrop High School, Headley attended Northwestern University from 1993 to 1996, to study communications and musical theater until the last day of her junior year, when she made the decision to become a part of the musical Ragtime and drop out of school. Headley attended Northrop High School, and was a member of their resident show choir, Charisma, and starred as Fanny Brice in the school’s production of Funny Girl. In 1989, she moved to Fort Wayne, Indiana in the United States at the age of fifteen with her mother and brother Eric Junior when her father was offered a job as pastor of McKee Street Church of God with headquarters in Anderson, Indiana. Headley was born in Trinidad, the daughter of Hannah and Eric Headley (Barbadian).
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