Cole Swindell Hints at Potential Engagement to Girlfriend Courtney Little

by Lauren Boisvert
(Photo by Jason Kempin/Getty Images for CMT)

Cole Swindell may have just hinted that he’s going to propose to his girlfriend, Courtney Little, pretty soon. Swindell and Little attended the CMA Awards on Nov. 9 together looking dressed to impress. This is the second time they have attended the red carpet together.

Before the awards ceremony, Cole Swindell caught up with E! Insider and dished about his relationship with Little. When asked if there are wedding bells in the future, Swindell replied, “I think that could happen,” with a smile. “We’ll see.” He also shared that he’s been thinking about engagement for a while.

“That’s something that I’ve obviously thought about,” he said. “I’ve just been waiting on the right person. And I feel like we’ve been together over a year now. So, it’s been nice. I’m happy. She’s happy, and we’ll see what happens.” 

Swindell and Little have been dating since 2021 when she appeared in Swindell’s music video for “Some Habits.” They had immediate chemistry in the romantic clip from the video. Swindell has said before that he considers the day on set their “first date.”

“That was kind of our first date having to act like it was a love song video, and we didn’t really know each other,” Swindell recalled. “We always laugh and say we wish we could go back and reshoot it. Now that we actually are together and feel the way we were acting in the video.”

As for Courtney Little, she and Swindell actually met once before the video, when Little worked for Monster. Additionally, she was Miss Teen North Carolina in 2017 and a former NBA dancer before she became co-owner of The Little Sisters Boutique.

Cole Swindell Hints at Wedding Bells For Him and Girlfriend Courtney Little

Cole Swindell continued to gush about his girlfriend, saying that he’s been waiting for a relationship like this for a long time. “I’ve waited a long time for this,” he told ET. He also shared that he was enjoying having her by his side at the CMA Awards. “This is the best feeling in the world,” he said. “I’m excited to have her with me and just to be able to celebrate this with someone. It just feels different.” 

Little has also appeared in the music video for Swindell’s newest hit “She Had Me At Heads Carolina.” She was also the inspiration for the song “Miss Wherever.” That song is a reference to Little’s previous involvement in beauty pageants.

Starting in May, Cole Swindell will join Thomas Rhett on his Home Team Tour. Swindell will be wrapping up his Back Down to the Bar Tour on Dec. 8, play a few festivals, and then join Thomas Rhett on the road. It should prove to be a great show.