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In 1998 Ashley Coleman decided to enter her first pageant, Miss Delaware Teen USA, she ended up not winning, but did not give up and returned a year later in 1999 and won the state title. Sending herself to Miss Teen USA.

At Miss Teen USA 1999, Ashley's first national competition, she walked away with the title and crown. Becoming the first and (as of 2019) the only Teen from Delaware to win the national title! Ashley also won the award for best in Swimsuit at the pageant. Her Miss Teen USA 1999 scores were (out of 10), 9.73 in interview, 9.65 in swimsuit, and 9.77 in evening gown, giving her an average of 9.71! After being crowning Miss Teen USA 199, she was sent to New York to spend her reign next to her pageant sister, Miss USA 1999, Kimberly Pressler!

During her reigning year, she graduated from high school, Caesar Rodney High School.

Before her state pageant, Ashley had modeled for Tommy Hilfiger, Rite Aid, and Johnson & Johnson, as well as Seventeen and Teen People.

After winning the state pageant Ashley changed her University Plans, she had planned to attend the University of Miami. But due to wanting to represent her title at home, she attended Delaware State University, completing three years toward her degree in education, one year prior to finishing her studies, she decided to take a break and enter the entertainment world. And moved to Los Angeles in 2003!