Entertainment Music Country Cole Swindell's Fiancée Courtney Little Shows Off Massive Engagement Ring on 2023 ACM Awards Red Carpet "It's hard to put into words how happy I am," Swindell, who's set to perform at the ceremony, told PEOPLE of the engagement earlier this week By Jack Irvin Jack Irvin Jack Irvin has over five years of experience working in digital journalism, and he’s worked at PEOPLE since 2022. Jack started in the industry with internships at Rolling Stone and Entertainment Tonight, and he worked as a freelance writer for publications including Bustle, MTV News, Shondaland, L’Officiel USA, Ladygunn, Flood and PopCrush before joining PEOPLE. In his current role, Jack covers daily music news and has interviewed both up-and-coming and established artists including Dolly Parton, Michelle Branch, Ashanti, Cyndi Lauper, Normani, Carly Rae Jepsen and Coco Jones. People Editorial Guidelines Published on May 11, 2023 06:45PM EDT Cole Swindell and Courtney Little. Photo: Jason Kempin/Getty Cole Swindell and Courtney Little are in engagement bliss! The country star and his new fiancée walked the 58th Academy of Country Music Awards red carpet together on Thursday and shared a kiss as Little, 24, showed off her engagement ring. Swindell, 39, proposed to Little on Sunday at the location of their first date — a farm north of Nashville, Tennessee — and she said yes. "It's hard to put into words how happy I am," he told PEOPLE earlier this week. "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," continued the "Never Say Never" musician. "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." Cole Swindell and Courtney Little. Matt Baron/BEI/Shutterstock Check out PEOPLE's full ACM Awards coverage to get the latest news on country's big night. A few weeks before the proposal, he spoke to Little's father about his intentions. "That's probably the most nervous I've ever been because he's such a great man," Swindell said of his soon-to-be 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," he continued. The singer-songwriter considered popping the question in Dallas this week during festivities leading up to the ACM Awards, but he ultimately chose the farm because of their connection to the location. The couple's first date was Swindell's "Some Habits" video shoot — in which Little starred — and was shot on the farm. Cole Swindell and Courtney Little. Jason Kempin/Getty Cole Swindell Engaged to Courtney Little: 'I Couldn't Wait Any Longer' (Exclusive) "She recognized the location," he 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 asked Little if she remembered the place, and he told her how special the location would always be to him. "At that point, I couldn't wait any longer," he said. "I found a little spot right there off the side of the gravel drive in the field and hit a knee." Watch Dolly Parton and a 'Nervous' Garth Brooks Hilariously Get Ready to Host the 2023 ACM Awards (Exclusive) Swindell is up for four awards at this year's ceremony, including single of the year, song of the year and visual media of the year for "She Had Me at Heads Carolina" as well as music event of the year for the song's remix with Jo Dee Messina, whose 1996 single "Heads Carolina, Tails California" is sampled in the hit. The pair is set to perform the remix during the show, co-hosted by Garth Brooks and Dolly Parton. The 58th Academy of Country Music Awards are airing live from Ford Center at The Star in Frisco, Texas Thursday, May 11 at 8 p.m. ET/5 p.m. PT and stream live exclusively on Prime Video.