And with a boy no less!
Of course it's with his new pooch, Pancho, so don't get too excited or collect on those longstanding bets just yet.
Kenny sent in a picture to PeoplePets.com and explained how his new pal Pancho came into his life last January.
"A friend gave it to me and said, 'Here, Kenny, you have to learn to attach to something!' God's honest truth!" Chesney tells PEOPLE. "Now, I love the guy."
Pancho is a goldendoodle -- half golden retriever and half poodle -- who joined Kenny in January. Now Kenny's a normal pet owner who goes crazy buying needless things at the petshop to keep his pal happy.
"Next thing you know, next day at PetSmart, I'm buying stuff, buying things and I have no idea!" he says. "That's just a dog! I can't imagine having three kids [like McGraw has]."
If you're going to stop by the Brothers of the Sun Tour, make sure and keep an eye out for Pancho because Kenny's going to see how he does as a roadie.
"The plan is to take him on tour," he says. "We'll see if he's got what it takes."