Fans were intrigued by the brief dating period and unexpected wedding of country legend Kenny Chesney and Academy Award-winning actress Renee Zellweger in 2005. However, they were far more intrigued when Zellweger filed for an annulment only four months later.

A lot of speculation swirled about the separation, but neither Chesney nor Zellweger said much about it. In 2010, Chesney finally explained to Oprah Winfrey that he looks at his life as a box that everything important must fit into, and his marriage to Zellweger sadly never made it into his box.

Chesney told Oprah, "It really is tough, and she's a sweet soul, no doubt about it, but I just wasn't ready [...] This is the first time I've actually talked about it, but that's what happened." It seems the split was for the best, as both artists have gone on to have successful careers and happy personal lives.