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
Watch: Chase Stokes Officially Confirms He's Dating Kelsea Ballerini

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:

January 2024: Happy Anniversary

The two celebrate the anniversary of their first date.

January 2024: Watching the Sunset

Kelsea shares this romantic pic on their first dating anniversary.

January 2024: Naughty Selfie

"A whole trip around the sun with my bestie," Kelsea writes in her anniversary post. "@hichasestokes thanks for making me write love songs."

January 2024: Chase's Anniversary Post

"One year of lovin you," the actor writes. "P.s. told ya I wouldn’t embarrass you."

November 2023: Sex Confession

Kelsea revealed details of their sex life in November 2023, 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."

November 2023: Loving Like They Mean It

Kelsea plants a smooch on Chase's cheek at the CMA Awards in November 2023.

September 2023: A Black Tie Affair

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

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

September 2023: All Smiles

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

September 2023: Birthday Love

To commemorate Kelsea's 30th birthday on Sept. 12, 2023 Chase posts a carousel of photos and videos of the three-time Grammy nominee. 

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

September 2023: Couple's Selfie

Kelsea unveils this pic on Chase's 31st birthday days later.

September 2023: Red Hot

The two appear together at the 2023 MTV VMAs on Kelsea's birthday.

September 2023: Red Carpet Romance

The two share a kiss at the event.

August 2023: NYC Date Night

The two are spotted on a summer date in NYC, where she performs on TODAY.

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

August 2023: Ciao Bella

The couple only have eyes for one another at a Venice Film Festival event.

July 2023: The Sweetest Surprise

Chase shocks Kelsea when he unexpectedly greets her at the airport, with both stars posting video and photos from their adorable reunion. 

July 2023: PDA Alert

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

May 2023: Hometown Visit

Chase joins Kelsea on a trip to her hometown of Knoxville, Tenn.

April 2023: Red Carpet Debut

The pair officially step out as a couple at the CMT Music Awards.

April 2023: Broadway Baby

The twosome attend the premiere party for the Broadway musical Shucked at Capitale.

April 2023: Award Show PDA

The two showcase their love on the CMAs red carpet.

February 2023: Instagram Cuteness

Chase shares a pic of himself and Kelsea showing some PDA.

January 2023: First Date Nerves

In August 2023, Kelsea posts footage of the beginning of their relationship, sharing a throwback clip on TikTok of herself preparing for their first official date on Jan. 7, 2023. 

"Happy weekend," she captions 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?"

January 2023: Romance Rumors

The two are photographed looking cozy at a football game.

December 2022: Shooting Her Shot

Kelsea Ballerini slides 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 recalls on Call Her Daddy in November 2023, "and he grabbed my face and he kissed me and he pulled my face away and he said, 'Thank God you're real.'"

December 2022: Shooting Her Shot

Their romance blossomed after that first DM, which Kelsea shares in September 2023.