Cole Swindell & His Girlfriend Are Engaged – More about Courtney Little

Country music star Cole Swindell and his girlfriend, Courtney Little, have taken their relationship to the next level as they recently got engaged. The couple had met years ago while she was at work, and it wasn't until years later that they had their first date while he was working.

Cole Swindell is a singer and songwriter who emerged as a prominent figure in the breezy country-pop genre, commonly called bro-country, during the 2010s. The Georgia-born singer was in college when he decided to pursue music.

He attended Dawson's Terrell Academy before graduating from Georgia Southern University in 2007. While at school, he met fellow country singer and songwriter Luke Bryan, and they quickly became friends.

Upon graduation, he joined Luke's team and wrote chart-topping songs for him. By 2010, Cole joined a publishing company and wrote songs for other musicians before releasing his first single, "Chillin' It," in 2013.

His single launched his career, and he released his debut album the following year. He has since released several other EPs and albums. Alongside his flourishing career, the singer has found joy in his personal life, having met his girlfriend, who has now become his fiancée.

'I Can't Wait to Be Part of Her Family' - Cole Swindell on Getting Engaged to His Girlfriend

The day Cole went to ask his future father-in-law's blessing to marry his daughter was one of the tensest experiences in the country crooner's life. He revealed her father is a good man and said:

"I can't wait to be part of her family. She comes from a good one, which made that so nerve-wracking. I can't imagine being a dad of a daughter and having that conversation."

With the backing of the Little family, the "You Should Be Here" hitmaker considered popping the question in Dallas ahead of the 58th ACM Awards but remembered a more meaningful spot in their relationship, on the farm where they had their first date.

With his girlfriend's sister, Laura Little's stamp of approval of the concept, he started putting his plan together. First, he co-designed a ring with Ballantyne Jewelers in Charlotte, North Carolina.

He had a representative of the jeweler personally get on a plane to deliver the jewelry. To add to the potential high-stakes drama, Taylor Swift's "The Eras Tour" caused a traffic jam when he headed out to collect the custom-made ring in downtown Nashville.

Finally, everything was set when the couple got on his tour bus on Sunday, May 7, 2023, en route to ACMA rehearsal and the secret proposal.

Cole had told her that they would be stopping for dinner to ensure she was dressed for the moment. His hope for a romantic sunset was dashed when rain poured down on the area most of the day.

They both blacked out and couldn't recall the exact words they exchanged with each other.

Luckily, they were blessed with a small break in the weather, and when their bus pulled over, Courtney initially thought the bus had broken down but soon recognized the location.

The duo went on a short walk hand-in-hand that was only a few minutes but felt like a long time for someone with a ring burning a hole in his pocket. He says:

"At that point, I couldn't wait any longer. I found a little spot right there off the side of the gravel drive in the field and hit a knee."

The singer humorously shared that their overwhelming excitement caused a momentary lapse in memory, jokingly suggesting that they both blacked out and couldn't recall the exact words they exchanged with each other. They are both eager to cherish and remember every detail of their special moment.

Though the words uttered might be lost forever, the intent was clear, and she responded in the affirmative. "The Ones Who Got Me Here" singer gushed:

"I put the ring on her finger, and we've been all smiles ever since."

A photographer captured the singer's proposal by hiding in the field at his request. The pair also tried to recreate some of their earliest photos at the farmhouse.

"Woke up as future Mrs. Swindell. I've never been so happy! I can't believe we are ENGAGED!!" Courtney wrote on May 8, 2023, when she shared the photos from the shoot.

She showed off a sizable oval engagement ring in the first image of the carousel, which ends with them popping a bottle of bubbly in the road. "Still couldn't tell ya everything I said down on one knee," the singer-songwriter wrote in his post with a similar selection of snaps the same day. "All I know is she said 'YES'!"

Courtney Little Is a Former NBA Dancer

The former Miss Teen North Carolina used to dance with the Honey Bees, affiliated with the NBA's Charlotte Hornets. Her Instagram bio states, "She will be known by the boldness of her faith."

Courtney is not the only former dancer of the Charlotte-based team to snag a country star. Brittany Aldean was in an earlier iteration of the Honey Bees squad a few years before she married Jason Aldean.

Courtney and her sister Laura are self-proclaimed stylish sisters who run an online clothing store, The Little Sisters. They assure customers that everything on the website is "sister-approved."

Courtney met Cole through her work as a Monster Energy Girl. The singer is an enormous NASCAR enthusiast, and with Monster being one of the major sponsors of the sport, the duo's paths crossed a few years ago.

They exchanged numbers and stayed in touch. On a radio show in October 2021, he said it "never was anything" more than friendship, and they would randomly see each other around. The "Some Habits" music video "kind of changed everything."

In the lead-up to the video shoot, the two had been texting more frequently. Two days prior, the singer asked his management team if he could put who he wanted in the video, and they agreed. Courtney was flown out to make the music video with the musician, which also served as their defacto first date.

They had gone Instagram official around the time of the music video's September 2021 release. No word yet if the farm that was the backdrop of their first date and proposal will be used again when they decide to get married.