May 9, 2005 - December 20, 2005 (annulled)
On May 9, 2005, Chesney married actress Renée Zellweger in a ceremony on the island of St. John. They had met in January at a tsunami relief event. On September 15 of that same year, after only four months of marriage, they announced their plans for an annulment. Zellweger cited fraud as the reason in the related papers, and after media scrutiny of her use of the word "fraud", she qualified the use of the term, stating that it was "simply legal language and not a reflection of Kenny's character." Chesney later suggested the failure of his marriage was due to "panic" from the intense media scrutiny surrounding it. In an interview by 60 Minutes with Anderson Cooper, Chesney commented on the failed marriage. "The only fraud that was committed was me thinking that I knew what it was like...that I really understood what it was like to be married, and I really didn't." The annulment was finalized in late December 2005. Chesney's family still resides in east Tennessee.