She responded to Playboy's "Who Wants to Be a Playboy Centerfold?" search when it came to Cleveland and was selected as a finalist for the competition. She, however, had second thoughts and withdrew early in the taping of material for the Fox Network special that aired in the summer of 2002. DeCesare then changed her mind about posing for Playboy and was quickly named Cyber Girl of the Week in October 2002 and Cyber Girl of the Month in February 2003, before being selected as Playboy's Miss April in 2003.

She appeared in the 2005 Playmates at Play at the Playboy Mansion swimsuit calendar as calendar girl of March. The calendar was the inaugural Playmates at Play calendar and it was shot on the grounds of the Playboy Mansion in 2004. It was Playboy's first attempt at creating a non-nude swimsuit calendar featuring Playmates similar in style with those from Sports Illustrated Swimsuit Issue. In 2005, DeCesare received breast implants. In an episode of the E! reality-TV series Th