Happy coincidence, then, that the crooner seems all too willing to share that his 2005 split from the Oscar winner was a major inspiration behind his new opus, Lucky Old Sun.
"It's no secret—there are about four or five songs that are about Renée," Chesney tells USA Today, adding that he began penning the two-years-coming disc just weeks after his annulment.
"It's a pretty emotional record for me, a very honest record. There are some songs on this record that needed to be written."
Whether Zellweger agrees with his creative assessment remains to be seen.
"I have no idea," he professes to Newsweek when asked how his famous ex may react to the tunes. "I don't know. It's unpredictable...I don't want to say this whole record is about her."
It was, however, motivated by her, or at the very least, the loss of her in his life.
"In 2006, I was probably as emotionally and mentally exhausted as I'd ever been. And that was due to a lot of things—having the foot on the gas pedal constantly, and my breakup with Renée Zellweger.
"It's the truth. It's my life. I've been in a lot of states of mind in the last three years...I've let myself be more emotionally vulnerable in some of the lyrics. I think that was good therapy.
Chesney goes on to say that while he speaks to Zellweger "every now and then," the breakup itself "was horrible" and not easily overcome.
"It took a while. Years. It's been since 2005," he confesses in the magazine.
Still, he's quick to note that he's far from hung up on the relationship and, while he once was, is no longer heartbroken over its demise.
"Not at all. I already wrote those songs. I'm on to something else."
The two-disc deluxe version of the album is set for release tomorrow. The single-disc version drops Oct. 21.