Cole Swindell Is Engaged to Girlfriend Courtney Little

Cole Swindell is getting married! The “Drinkaby” singer proposed to his longtime girlfriend, Courtney Little, sharing a few photos of him getting down on one knee and popping the question.

“Still couldn’t tell ya everything I said down on one knee.. All I know is she said “YES”!” Swindell shares. “We’re so excited!”

Swindell’s first date, of sorts, with Little was the video for “Some Habits,” which he asked her to star in. From there, sparks flew, which is why he included so many love songs on his latest Stereotype album, out last year.

“I think any time before now, it might have been just what the audience wants to hear,” Swindell told Everything Nash and other outlets, during a media event in 2022. “I know that I’ve had a lot of breakup songs. They’re not love songs … I always say, I can’t write or sing a song unless I’ve been through it, want to go through it, or it makes me feel something. And I think that’s why I haven’t recorded too many up until this album.

“But I think this one’s got songs like ‘Some Habits,’ ‘I’m Gonna Let Her,’ things like that that I just I feel every word to,” he added. “I’m living in that, and I didn’t know if I’d ever find that. I think that the fact that I have is just … I’ve always wanted to. I know how fortunate I am to have this career. I’ve got friends and family, but you want somebody to share that with.”

While it might have taken the 39-year-old a while to find true love, he is glad he finally has a muse for the romantic tunes on Stereotype.

“I think with this album, I think there are touches of that in there, love songs that I can sing and know I’m not just singing them,” Swindell explained. “I think I feel that now. And so it’s always better when it makes you feel something, and these do. I do enjoy getting to talk about that now … I’m happy talking about it now because I think I am happy and I think that’s only going to make my music for years to come hopefully even better.”

Swindell and Little will have to do at least some of their wedding planning long-distance. The singer-songwriter is currently on the road, serving as the opening act for Thomas Rhett on Rhett’s Home Team Tour. He will follow that with his own headlining Twelve Tour this fall.  Find music and tour dates at ColeSwindell.com.