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Home Celebrity Engagement Rings

Courtney Little’s Engagement Ring and Love Story with Country Star Cole Swindell!

Rallye Ibanez by Rallye Ibanez
May 29, 2026
in Celebrity Engagement Rings, Engagement Rings
Reading Time: 7 mins read
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Courtney Little Engagement ring
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Courtney Little’s engagement ring from country star Cole Swindell finally elicited her lovely yes! Cole proposed to her on May 8, 2023. True to his country roots, he proposed on a farm outside Nashville, too!

To get a professional appraisal on this precious ring, we had an EXCLUSIVE phone call with Benjamin Khordipour G. D., the GIA-certified gemologist and jewelry specialist from NYC’s Estate Diamond Jewelry. Click here to see what he said.

More Details on Courtney Little’s Engagement Ring and

On May 8, 2023, Cole and Courtney became one of the happiest couples in Hollywood when they got engaged on a farm outside of a Nashville estate.

It’s where Cole also filmed his “Some Habits” hit music video starring Courtney. It’s also where they had their first date, making it a special place.

Courtney Little’s engagement ring features an approximately 4-carat oval-cut solitaire diamond with a prong setting on a white gold or platinum band.

View this post on Instagram

A post shared by Courtney Little (@courtney0little)

Cole and his fiancée shared their happy engagement news on the same day on Instagram.

The former NBA dancer and entrepreneur had no idea about the proposal. Cole had set up the whole shebang as a special surprise.

They were supposed to attend the 2023 Academy of Country Music Awards in Frisco, Texas. He told her they were going to the dress rehearsal for the event, where he was also attending.

Their bus was really bound for the southwest toward Texas. When they got to Orlindan town, he had already set up the proposal in the lovely location. Courtney said yes to his promise of their forever, and they celebrated with a bottle of champagne.

They debuted as an engaged couple at the AMC Awards Show, 3 days later, on May 11, 2023.

Courtney Little's Engagement Ring from country star Cole Swindell!
https://www.instagram.com/courtneylswindell/

How Much Is the Ring Worth?

Our phone conversation with the Gemological Institute of America-certified gemologist and jewelry specialist, Benjamin Khordipour G.D., from NYC’s Estate Diamond Jewelry, revealed its specs. He also gave us professional insights into the ring.

His price tag for this exquisite ring is $100,000. Some main considerations dictate the price of this ring.

Courtney’s engagement ring features a high-quality, 4-carat oval-cut diamond secured with prongs in a north-south placement. 4 prongs cradle the ring, set on a thin gold band.

Simon Tekin at Ballantyne Jewelers in Charlotte, North Carolina, collaborated with Cole on the ring’s design and creation. The minimalist design focuses attention on the center stone.

The Oval-Cut Diamond and Its Features

An oval-cut diamond has advantages and good features. It still offers a roundish shape with the same fire and brilliance as a round brilliant-cut diamond. Its elongated shape makes the stone look much bigger on the finger.

An occasional negative to an oval-cut diamond is the bowtie effect. This is the presence of a bowtie-shaped shadow beneath the stone.

Because of its elongated oval shape, these dark spots on the center stone are more visible. The severity of the bowtie effect depends on the cutting. This can be more prominent on oval diamonds with a length-width ratio of 1.5 and higher.

While others do not like this bowtie effect on the diamond’s beauty, some like the unique effect and shadow.

An oval-cut diamond’s length-width ratio makes it rounder or longer, depending on the proportions. The oval cut diamond is most appealing between a 1.30 and 1.50 ratio. A 1.30 ratio gives it a more roundish look, while 1.60 makes it more elongated.

Cole and Courtney’s Love Story

Many celebrities meet and fall in love because they were at their jobs. Courtney used to be a Monster Energy drink dancer and she was one of their event dancers in a NASCAR event that Cole attended years before they worked together and dated.

He told their first meeting on the Bobby Bones show, explaining that “We met several years ago actually. You know, I’m a big NASCAR fan, and she works with Monster. 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.”

He cast her in his 2022 hit music video “Some Habits”, which set off their love story.

Cole spoke to PEOPLE about it, “That was kind of like our first date. Pretending like you’re in a relationship on camera, that was pretty awkward. That was the first time we really got a chance to hang. We went out after we shot the video, and we’ve been together ever since.”

Cole proposed to her on the same spot they first dated, and the setting of his “Some Habits” music video, bringing their relationship full circle.

Courtney captioned her Instagram post with, “Woke up as future Mrs. Swindell 💍 I’ve never been so happy! I can’t believe we are ENGAGED!!!!!” Cole nervously approached the proposal and planning by asking for Courtney’s father’s permission first. His photographer hid in the greenery and took their beautiful photos.

Cole and Courtney’s Profiles


Cole, or Colden Rainey Swindell, born on June 30, 1983 in Glenville, Georgia, is one of the newschool country music stars in the music biz. His hits such as “Some Habits”, “Chillin’ It,” “You Should Be Here,” “Flatliner,” “Never Say Never,” and “She Had Me At Heads Carolina” went to number 1 on many nationwide country charts.

He first started his career as songwriter for country music artists such as Luke Bryan, Craig Campbell, and Florida Georgia Line. He signed on a publishing deal with Sony/ATV Music Publishing in 2011.

His string of hit singles eventually led to his self titled album in February 18, 2014, after he signed with Warner Music Nashville. Cole also won the Academy of Country Music New Artist of the Year Award in April 2015.

Over the next few years, he released a succession of successful country and country pop albums, “You Should Be Here” (2016), “All of It” (2018), and “Stereotype” (2022).

Courtney Little was an NBA dance squad team for the Charlotte Hornets Honey Bees, along with her big sis, Laura Little Sock. Together, they own The Little Sisters Boutique. She was also 2017 Miss Teen North Carolina.

Courtney also worked as a Monster Energy Girl, appearing in the X Games and NASCAR events. She eventually met Cole at one of these NASCAR shows, where he got her number and kept in touch.

Their first date was on his music video shoot.




Tags: Cole SwindellCourtney Little Engagement Ring
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