In for the long run
Nolan is his current girlfriend, and the two have been going out steady for seven years now. For all we know, this is Chesney’s longest relationship so far. He also shared in an interview that back in high school he wasn’t much of a ladies man (though he was in the baseball team, go figure), and so his success with women only came later in life.
In every one of his relationships it seemed like he was in for the long run, but we’re guessing that after divorcing Rene Zellweger after only four months, he wouldn’t repeat the same mistake of getting married before he’s absolutely ready.