Yee Haw For Love! Cole Swindell And Courtney Little Are Engaged

Just days after releasing a deluxe edition of his stellar fourth album, Cole Swindell has made even bigger news by taking a personal leap forwards – he and his girlfriend of two years, Courtney Little, are officially engaged.

Swindell broke the news on Instagram last night (May 8), sharing a quadrant of photos from the proposal. He appears to have popped the question on a grassy field along the eastern US countryside (he performed in Indianapolis on Monday), with grey clouds above adding some beautiful contrast to the setting. 

“Still couldn’t tell ya everything I said down on one knee,” the Chillin' It hitmaker wrote in a caption. “All I know is she said ‘YES’! We’re so excited!”

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Little – a former NBA dancer and the 2017 Miss Teen North Carolina model – also shared the news on Instagram, writing that she’s “never been so happy” and “can’t believe we are ENGAGED”.

Swindell and Little started dating around two years ago, with their first public appearance coming at the 2022 CMT Music Awards. They reportedly met on the set of the music video for Swindell’s single Some Habits, which the Franklin, Tennessee native has dubbed their unofficial first date. 

Some Habits appears on Swindell’s latest album, Stereotype, which arrived last April via Warner Music Nashville. It featured three singles – Single Saturday Night, Never Say Never and She Had Me At Heads Carolina – and was recently updated with three new tracks for the Stereotype Broken deluxe album. As well as the new single Drinkaby, the reissue (which landed on April 28) features new cuts Sad Ass Country Song and Broken, plus a remix of She Had Me At Heads Carolina featuring Jo Dee Messina.

“My fourth studio album has done so much for us this past year,” Swindell said in announcing Stereotype Broken. “I felt we had a few more songs that deserved to be part of the project and I can’t wait for y’all to hear them."