Entering high school, Kelly discovered the Drama program at Kamehameha High School. She was so passionate about the class she signed up for it every semester for four years. The summer after her sophomore year she got the opportunity to travel with the Drama Club to the International Thespian Conference in Muncie, Indiana.

On this same trip, Kelly experienced her first Broadway play in New York and visited Universal Studios in Los Angeles, reinforcing her desires to become an actress.

While still in school, Kelly was scouted by a modeling agent at a shopping mall who happened to represent Kelly's cousin, a very successful model in Japan at the time. Capitalizing on the Japanese intrigue with American beauty pageants at the time, her agent suggested that Kelly take a class in modeling and try to win a pageant title to help better promote her in Japan. Fueled by the thought of making some quick money over the summer and the chance to travel, she took the agents advice.

While enrolled in a photo posing class, Kelly heard about a local beauty pageant called Miss Hawaii Teen USA. She entered the pageant with the hopes of winning the local title and taking off to Japan that summer to a contract that was already signed and waiting for her.