Cole Swindell Details Romantic Proposal To Courtney Little

Cole Swindell is sharing details of his romantic proposal to his now-fiancée, Courtney Little. The singer, who has been dating Little since 2021, first asked her father for permission to marry his daughter, which Swindell admits made him more than a little anxious, and with good reason.

“That’s probably the most nervous I’ve ever been because he’s such a great man,” Swindell tells People. “I can’t wait to be part of her family. She comes from a good one, and that’s what made that so nerve-wracking. I can’t imagine being a dad of a daughter and having that conversation.”

Swindell chose an oval diamond ring from Ballantyne Jewelers in North Carolina, asking someone to fly to Nashville to hand-deliver it to Swindell on Sunday morning in downtown Nashville, although the Georgia native didn’t anticipate how hard that would be, thanks to the tourists in town for the Taylor Swift weekend of concerts.


“It looked like [Swift] was playing acoustic pop-up shows outside of restaurants or something,” Swindell says. “There were lines all over the place. And I was like, ‘This is not what I envisioned coming.’ I was trying to get down there early to get it before all that, but I did not miss any of it.”

Still, with a ring in hand, Swindell got Little on his bus, telling her that they were heading to Dallas for his ACM Awards rehearsals, where he is one of the performers. Swindell told her they were stopping somewhere for dinner, to make sure she was dressed well for the engagement photos. But instead of heading towards Dallas, the bus drove toward Orlinda, where his “Some Habits” video was shot, and where their romance began.

“She recognized the location,” Swindell shares. “She probably knew what was going on then. I took her hand and walked for what felt like a long time. It probably wasn’t but a minute or so.”

“At that point, I couldn’t wait any longer,” he added. “I found a little spot right there off the side of the gravel drive in the field and hit a knee.”


Although neither Swindell nor Little remember what either of them said to each other in that moment, they are still euphoric that they now get to plan their future together as husband and wife.

“I put the ring on her finger, and we’ve been all smiles ever since,” Swindell says.

The “Drinkaby” singer, who included love songs on his latest Stereotype album, thanks to Little, is overjoyed that he has found true love.

“It’s hard to put into words how happy I am,” Swindell says. “I feel like I’m very fortunate to be where I am in my career, but I feel like I’ve missed out on a lot of real-life moments. I’m just glad to have somebody to share everything with. She makes me better, and I’m the happiest I’ve ever been in all parts of my life.”

Swindell is currently on the road, serving as the opening act for Thomas Rhett on Rhett’s Home Team Tour. He will follow that with his own headlining Twelve Tour this fall. Find music and tour dates at

Photo Credit: Getty Images for CMT and Cole Swindell/Twitter