Look Back on Kelsea Ballerini and Chase Stokes' Cutest Pics

Kelsea Ballerini, who turned 30 on Sept. 12, and Chase Stokes haven't been shy about sharing their relationship since she slid into his DMs. Look back on their adorable road to romance.

By Tierney Bricker Sep 12, 2023 8:45 PMTags

Once upon a time, a country pop star met a Pogue on Instagram...

Kelsea Ballerini and Chase Stokes might just be the modern-day version of a fairy tale romance, with the couple's relationship only getting sweeter since they first sparked dating rumors in January 2023. And, it turns out, Ballerini was the one who initially pursued Stokes, as the singer-songwriter revealed on the Call Your Daddy podcast that she slid into the Outer Banks actor's DMs.

Now that's leading with your heart first

Ballerini, who split from Morgan Evans after five years of marriage in August 2022, and Stokes, 30, haven't been shy about showing their affection for one another since then, whether it's PDA on the red carpet or sharing adorable snaps on Instagram.

Stokes declared his love for the "Love Me Like You Mean It" artist with a gushing Instagram tribute for her 30th birthday on Sept. 12. "dirty 30 looks pretty damn good on you ballerini," Stokes captioned the post. "i love you."

The series caps off a summer filled with love for the couple, who went on a dreamy Italian getaway and attended a Jonas Brothers concert, with Ballerini telling E! News she is looking forward to what lies ahead as she steps into her next era. 

They Dated? Surprising Star Couples

"I feel really content that I have lived every ounce of my 20s," Ballerini told E! News ahead of her milestone birthday. "I have no regrets and feel like I left no stone unturned. I feel lucky to have so many experiences under my belt and I feel ready to turn a new page."

In honor of Ballerini's turning the big 3-0, we're looking back on her cutest moments with Stokes:

Jumping Heartfirst

Kelsea Ballerini slid into Chase Stokes' DMs on Dec. 1, 2022 at 1:30 a.m. while she was out drunk with friends at a bar.

They eventually met up in person for the first time on Jan. 7, 2023, which she considers their anniversary. 

"He hopped out of his Bronco, and he did not say a word to me," Kelsea later recalled on Call Her Daddy, "and he grabbed my face and he kissed me and he pulled my face away and he said, 'Thank God you're real.'"

Shooting Her Shot

A romance blossomed after that first DM.

"He shoots in Charleston and my manager lives there and he put the bug in my ear," the "Heartfirst" singer explained on the Call Her Daddy podcast. "I've never seen the show but I just knew of him and I followed him and he followed me and I just swan dove right on in."

The singer eventually shared the screenshot of their first convo in honor of her boyfriend's 31st birthday.


First Date Nerves

Kelsea would later post footage of the beginning of their relationship, sharing a throwback clip on TikTok of herself preparing for their first official date. 

"Happy weekend," she captioned the post, "heres a video i sent to my best friend before my first date with chase."

Set to her song "How Do I Do This," which is about going on a first date after many years, Kelsea models her outfit in the video.

"Here's the look, with the boots" Kelsea says while checking herself out in a full-length mirror. Turning around to showcase her half-up, half-down hairstyle, she adds, "We've got the hair clip, because we're trying to be a cool girl."

She continues speaking to an unnamed friend, explaining, "He's picking me up and we're going to a sushi place and I'll call you tomorrow and for a full update."

Taking a deep breath and raising one arm and finger in the air, she finally says, "I can do this. I can do this." And, after doing a little dance, she proclaims, "It's just a date. You just go and you just eat food and you talk about things that you do, OK?"

Romance Rumors

The two made their romance public in January 2023 when they were photographed looking cozy at a football game.

Instagram Cuteness

In February, Chase shared a pic of himself and Kelsea showing some PDA.

Red Carpet Debut

The pair officially stepped out as a couple at the CMT Music Awards in April 2023.

Award Show PDA

The two showcased their love on the red carpet.

Broadway Baby

The twosome attended the premiere party for the Broadway musical Shucked at Capitale in April 2023.

Hometown Visit

In May 2023, Chase joined Kelsea on a trip to her hometown of Knoxville, Tenn.

PDA Alert

The two attended Armani Beauty's ACQUA DI GIO and Gen A celebration in Malibu, Calif., in July 2023.

The Sweetest Surprise

Chase shocked Kelsea when he unexpectedly greeted her at the airport in July, with both stars posting video and photos from their adorable reunion. 

Ciao Bella

The couple only had eyes for one another at a Venice Film Festival event in August 2023. 

NYC Date Night

The two were spotted on a summer date in NYC, where she performed on TODAY.

"It's just nice to feel so supported and seen," Kelsea said on the show of Chase, "and, yeah, he's such a wonderful, wonderful human being."

A Black Tie Affair

Kelsea and Chase were dressed to the nines when they attended designer Giorgio Armani's "One Night Only" event on Sept. 2, 2023 in Venice, Italy. 

The singer-songwriter and the Outer Banks star shared images of their getaway on Instagram, including snaps from a cooking class and lounging at the beach.

All Smiles

Kelsea shared this behind-the-scenes look from the event.

Birthday Love

To commemorate Kelsea's 30th birthday on Sept. 12, Chase posted a carousel of photos and videos of the three-time Grammy nominee. 

"dirty 30 looks pretty damn good on you ballerini," he captioned the series. "i love you."

Red Hot

The two appeared together at the 2023 MTV VMAs on her birthday.

Red Carpet Romance

The two shared a kiss at the event.

Couple's Selfie

Kelsea unveiled this pic on Chase's 31st birthday Sept. 16, 2023.

Loving Like They Mean It

She planted a smooch on his cheek at the CMA Awards 2023 in November.

Sex Confession

Kelsea revealed details of their sex life in November, telling Alex Cooper on Call Her Daddy, "I'm having a nice time."

"My experience with it was very performative and for the other person," she noted. "And it don't be like that anymore."

The musician didn't understand how sex could be "a real connector in a relationship" before dating him.

"I always thought that it was just something that you did because that's who you do it with," the Grammy nominee shared. "Now I realize it's a connector for people."

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