Medley won her first major pageant title in 2001, when she won the Miss South Carolina Teen USA pageant held in November 2000. She represented her state in the Miss Teen USA 2001 pageant held in South Padre Island, Texas in August 2001, but failed to place in the nationally televised pageant, which was won by Marissa Whitley of Missouri. Medley is one of the youngest titleholders to win the state pageant, as she was only fourteen years old when she won. The following year, she competed in the Miss United States Teen pageant and placed first runner-up.2
In 2004, Medley returned to the pageant scene and won the Miss South Carolina USA title at eighteen, again one of the pageant's youngest titleholders in history. She competed in the Miss USA 2005 pageant but again did not place. The pageant was won by fellow Carolinas titleholder, Chelsea Cooley, Miss North Carolina USA. Both women represented RPM Productions and were former Miss Teen USA delegates.
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