Country Star Cole Swindell Engaged to Girlfriend, Who's the Star of One of His Music Videos

Country singer Cole Swindell and his girlfriend, Courtney Little, are engaged! Swindell, 39, proposed to Little, 24, on May 6, at the same spot where they had their first date. Little starred in Swindell's "Some Habits" music video.

The "Love You Too Late" singer shared photos from his proposal on Instagram Monday, including a picture showing off Little's engagement ring. "Still couldn't tell ya everything I said down on one knee. All I know is she said 'YES,'" Swindell wrote. "We're so excited!"

Swindell debated several different locations for the proposal, but he ultimately decided to go with a farm north of Nashville. It was the location for the "Some Habits" video shoot, which doubled as their first date. He only proposed after getting permission from Little's father.

"That's probably the most nervous I've ever been because he's such a great man," Swindell told PEOPLE of his future father-in-law. "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."

The engagement ring was designed by Simon Tekin of Ballantyne Jewelers, which is based in Charlotte, near Little's hometown in North Carolina. Swindell asked a representative from Ballantyne to hand-deliver the ring, which meant he had to brave Taylor Swift traffic to drive across Nashville to get it Sunday morning.

Later that day, Swindell and Little got onto his tour bus to head to Dallas for Thursday's Academy of Country Music Awards. Instead of going south, the bus began driving north. The bus eventually stopped by a gravel road. Swindell led Little along the road, and she soon recognized where they were.

"She recognized the location," Swindell told PEOPLE. "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." Swindell got to a point on the road where he just couldn't wait. He found a good spot to get down on one knee and proposed.

"It's hard to put into words how happy I am," Swindell told the magazine. "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 rose to fame as a songwriter before he released his debut single "Chillin' It" in 2013. His other hit songs include "You Should Be Here," "Flatliner," "Break Up in the End," "Love You Too Late," "Single Saturday Night," "Never Say Never" with Lainey Wilson, and "She Had Me at Heads Carolina." He plans to release a deluxe edition of his latest album, Stereotype and will perform at the ACM Awards, which stream on Amazon's Prime Video Thursday night.