BREAKING: Cole Swindell Engaged To Courtney Little

Cole Swindell and his longtime girlfriend, Courtney Little, are engaged!  The superstar announced their engagement on Instagram on Monday morning…


Lauren Jo Black

| Posted on

May 8, 2023

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Cole Swindell, Courtney Little; Photo Courtesy of Cody Arrington-

Cole Swindell and his longtime girlfriend, Courtney Little, are engaged! 

The superstar announced their engagement on Instagram on Monday morning (May 8). His post included sweet snapshots from their engagement as he admitted, “Still couldn’t tell ya everything I said down on one knee… All I know is she said “YES”! 💍

The singer/songwriter, added, “We’re so excited!”

Little also shared the news on social media.

“Woke up as future Mrs. Swindell 💍 I’ve never been so happy,” she sweetly shared. “I can’t believe we are ENGAGED!!!!! 🥹” 

The engagement ring features a large solitary diamond from Ballantyne Jewelers.  

Courtney Little, the co-owner of The Little Sisters Boutique, is a former NBA dancer and 2017 Miss Teen North Carolina. 

Swindell has been dating Little for quite some time now and she may look familiar to fans as she appeared in his music video for “Some Habits,” which was released in the fall of 2021.

YouTube video

The Georgia native previously opened up about their relationship and revealed how they met during an interview on The Bobby Bones Show.

“We met several years ago actually. You know, I’m a big NASCAR fan and she works with Monster and you know we just kind of met and exchanged numbers and kept in touch over the years, but it never was anything just kind of friends, randomly saw her here and there, but the video kind of changed everything,” Swindell shared at the time.

He later explained that he was the one to actually cast her in the clip and that the video shoot was technically their first date.

“She lives in Charlotte, and we were about to shoot the video for ‘Some Habits.’ I texted my team and I was like, ‘Hey, shouldn’t I see the list of people we’re picking from to be in this video?’ Swindell told Kelleigh Bannen on Today’s Country Radio with Kelleigh Bannen on Apple Music Country.

“I’m thinking about her. I’m like, ‘She might not like that. Let’s figure this out. This song means a lot to me.’ I kind of felt that way about her then, and I asked her, I said, ‘Hey, would you be willing to come to Nashville and maybe be in the video? It’s just going to be fun,” he recalled.

Luckily for Swindell, Little was up for it and took on the role of his love interest in the video for “Some Habits.”

“That was the first time we really got to spend more than 10 minutes together and hung out. Yeah, so kind of like a first date,” he said.

The couple made their red carpet debut at the 56th Annual CMA Awards and after turning heads during their arrival, Swindell talked to Taste Of Country Nights about bring Little along.

“I’m excited, this is our first one together,” Swindell explained.


He later admitted that this was the perfect awards show for Courtney Little to witness as he was not only performing, but was also nominated for several awards.

“I can’t imagine a better first one for her to see,” Swindell added. 

This is a big week for Cole Swindell. He recently joined Thomas Rhett for the opening of the Home Team Tour 23, and later this week, he’s set to perform at the 58th Academy of Country Music Awards. 

Cole Swindell; Photo by Andrew Wendowski
Cole Swindell; Photo by Andrew Wendowski

Swindell is a first-time ACM Awards nominee in three categories including Single of the Year, Visual Media of the Year, and Music Event of the Year, in which he shares a nomination with his collaborator and fellow artist Jo Dee Messina who received her first nomination in 22 years.

Following the ACM Awards, Swindell will return to the road for the Home Team Tour 23 in Omaha, NE.

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Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.