In July 2009, Pressly became engaged to entertainment lawyer Simran Singh. They married on September 26, 2009 at the Dick Clark Estate. Guests, including Pressly's two-year-old son Dezi James, attended the ceremony on a bluff overlooking the Pacific Ocean. On January 21, 2011, Pressly filed for divorce from Singh, citing irreconcilable differences. In her divorce petition, Pressly listed the couple's date of separation as December 27, 2010, nine days before her DUI arrest.