In May 2007, upon re-signing her contract with Vivid for another six films, Leone agreed to perform for the first time with men on camera, but exclusively with her fiancé, Matt Erikson. That summer she also received breast augmentation, and shot her first movie under the new contract titled "Sunny Loves Matt". The movie led to her being nominated for three (out of six) AVN awards in 2009 in addition to being a choice for Female Performer of the Year. She followed up her first boy-girl title with "The Other Side of Sunny" in October 2008, which would be the last time she would perform with Erikson.