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Presenting: Chase Stokes and Kelsea Ballerini’s Super Dramatic Relationship Timeline
2026-04-30 · via Latest Content - Cosmopolitan

After rolling up to the 2026 Grammys solo, it seems that Kelsea Ballerini and Chase Stokes are, once again, on the outs...and perhaps for good. TMZ broke the news of their latest split on February 6, less than a week after Kelsea opened up about getting back together with Chase on the Grammys red carpet, telling Entertainment Tonight of the breakup, “I feel like outwardly, it looked a lot more dramatic than it was. And that was quite the learning lesson for us.”

As you might recall, speculation about Kelsea and Chase’s romance first started after the Outer Banks star posted a pic of himself and the country singer at a football game on Instagram—and as they say, the rest is history. Let’s get into all the deets about these two and their on-and-off-again romance, shall we?

January 2023

Ah, the post that started it all! Chase takes to Instagram to low-key launch his and Kelsea’s relationship love of football in a photo dump that features a sweet pic of them watching the college football national championship game between the University of Georgia and Texas Christian University. Cue the dating rumors.

Soon after, Kelsea who posts a cryptic TikTok that includes a screenshot from the celebrity gossip account DeuxMoi about her and Chase.

“I know, I know, I know, I know, I know, I know,” the singer begins, a screenshot insinuating that she and the actor are a PR stunt posted behind her. “Stop reading, stop reading. Stop looking. But what is happening, guys? What? What? What? No, let’s not do this, you know?”

“I’m about to break up with the internet 5 sure 😂” is the caption to the video. 👀

Then, Chase actually addresses the relationship speculation IRL during a convo with TMZ. The actorcalls Kelsea a “sweet girl” and adds, “We’re having a good time, and that’s all I’ll say.” In-ter-est-ing!

And finally: TMZ snaps some preeeeetty spicy images and video footage of Kelsea and Chase kissing, hugging, and holding hands at California’s LAX airport. The proof is in the pap pics, people!

February 2023

During an interview with People tied to the premiere of Outer Banks season 3, Chase is asked about the pic he posted of himself and Kelsea, and he confirms that they “have just been spending some time together.”

He continues, “Kelsea is a lovely, lovely girl. She’s great. We’re having a good time.”

That VERY SAME DAY, Kelsea reposts a comment by someone who has written “@hichasestokes come get your girl” with a TikTok of herself sitting up in bed while wearing eye patches and sipping out of a teacup. She smiles to the camera and casually leans over to reveal what appears to be Chase’s tattooed arm.

A day later, Kelsea drops Rolling Up the Welcome Matan EP partially about her divorce from Morgan Evans—and on Valentine’s Day, no less. To show his support, Chase takes to his Instagram Stories to congratulate the country singer’s project. “So proud of you, your heart & your beautiful soul. Congrats Kels ❤️,” he writes alongside a v tender pic of himself and Kelsea.

kelsea ballerini and chase stokes

@hichasestokes/Instagram

And to close out the month, during a Call Her Daddy appearance, Kelsea reveals the coy way she and Chase first began talking: a DM slide. 😂

“I was ready to open back up,” the singer confesses to host Alex Cooper. “I just felt, why not? I’ve never really dated; I don’t know how it works. I’m like, ‘Let’s just put ourselves out there; let’s just vibe.’ And it’s been fun.”

The musician says she slid into Chase’s DMs after the two started following each other on Instagram. “I’ve never seen his show, but I just knew of him, and I just swan dove right on in... His handle is ‘@hichasestokes’ and I said, ‘Hi, Chase Stokes.’” S’cute!

March 2023

The duo has a sweet date night at Madison Square Garden when they attend the New York Rangers game against the Ottawa Senators. During the event, the songstress and actor are even photographed sharing a kiss from their seats. Oop!

Then, after months of social media posts that made their ’ship pretty damn clear, Chase finally *officially* confirms his coupled-up status during an appearance on the Today show. When Sheinelle Jones asks Chase flat-out if he’s dating Kelsea Ballerini, he smiles and says, “Mmhmm,” officially confirming the romance!

When Jones mentions Kelsea’s upcoming SNL appearance and asks if Chase is a fan, he answers like any good S.O. would, saying, “Absolutely I’m a fan. Yeah, who isn’t a fan?”

Oh, and Kelsea shuts down claims that she and Chase are a PR stunt with a simple Insta Story.

kelsea ballerini, chase stokes

@kelseaballerini/Instagram

April 2023

Chase and Kelsea go red carpet official at the CMT Awards and the photos are too cute.

2023 cmt music awards arrivals

Hubert Vestil//Getty Images

2023 cmt music awards arrivals

Renee Dominguez//Getty Images

cmt awards chase and kelsea

John Shearer//Getty Images

August 2023

Kelsea drops a never-before-seen video of herself getting ready for her very first date with Chase. It’s all very cute, so prepare accordingly.

Soon after, Kelsea plants a 🥺 kiss on Chase’s cheek while the celebs attend Variety and the Golden Globes’ Venice Film Festival party. Ahem, observe:

variety and golden globes party at venice film festival, presented by ilbe inside

Victor Boyko//Getty Images

September 2023

The two have an iconic date night at the MTV VMAs in matching red ’fits. You know what they say: The couple that slays together stays together!

2023 mtv video music awards arrivals

Gilbert Flores//Getty Images

2023 mtv video music awards arrivals

Jamie McCarthy//Getty Images

2023 mtv video music awards arrivals

Jeff Kravitz//Getty Images

Couldn’t be more obsessed if I tried!

October 2023

Kelsea opens up about her sweet ’ship during her cover story for Nylons It Girl Issue, gushing, “We are both very much so golden-retriever energy most of the time, but we both have a little bite in us, and we’re both incredibly driven. He is the first person I’ve been in a relationship with that I feel like is not my complete opposite.”

The musician also reflects on the early days of her relationship with the actor, which began with a first date in Los Angeles. “I really did [know] as soon as I met him,” she begins before adding, “And maybe that sounds like I’ve learned zero things, but I’ve always been a heart-first girl and the truth is it’s never led me astray. I’ve always been where I needed to be while I needed to be there.”

Then it’s their first Halloween! Shocker: She’s Barbie...and he’s just Ken, lol.

celebrity sightings in new york city october 25, 2023

Gilbert Carrasquillo//Getty Images

November 2023

Chase and Kelsea hit the red carpet at the 57th annual CMAs in Nashville and look literally perfect/so in love:

the 57th annual cma awards arrivals

Jason Kempin//Getty Images

the 57th annual cma awards arrivals

Taylor Hill//Getty Images

Later in the month, Kelsea makes another appearance on Call Her Daddyand gets incredibly real about her ’ship with Chase. “He’s the most emotionally intelligent man I’ve ever met in my life,” Kelsea tells Alex Cooper. “I keep telling him he’s a man written by a woman.”

Kelsea also reveals that her relationship with the Outer Banks star changed her perception of sex, saying, “My experience with it was very performative and for the other person. It don’t be like that anymore.”

She adds, “I didn’t understand how [sex] could be a real connector in a relationship. I always thought it was just something that you did…Now, I realize it’s a connector for people.”

December 2023

Kelsea and Chase spend Christmas together! And wear matching “Horny” sweaters.

January 2024

The celebs celebrate their first anniversary.

March 2024

The Outer Banks star gushes about how incredible his ’ship with Kelsea is to OK! Magazine. Ahem: “It’s been my favorite chapter of life, and she’s such a special human being.”

The actor also reveals that what makes their romance so amazing is how much they are there for each other. “I’ve been able to go on the road with her and watch her in her element. She’s been able to come and watch me work as well, so we’ve just been really, really loving this chapter of life, which has been great,” he muses.

April 2024

Kelsea and Chase step out for the CMT Awards and look beyond in love. I meannnnn:

2024 cmt music awards arrivals

Taylor Hill//Getty Images

2024 cmt music awards arrivals

Taylor Hill//Getty Images

May 2024

It’s the first Monday in May (IYKYK), and these two are celebrating.

met gala

John Shearer//Getty Images

August 2024

The pair goes to the opening night of the Intuit Dome in L.A. and have truly never looked cuter.

opening night of the intuit dome ribbon cutting ceremony and red carpet

Kevin Winter//Getty Images

September 2024

Kelsea attends the premiere of Chase’s movie Uglies and poses by his side.

netflix's uglies los angeles special screening

Roger Kisby//Getty Images

A few days later, Chase supports Kelsea’s acting debut in Doctor Odyssey, attending the premiere as her date.

doctor odyssey

Emma McIntyre//Getty Images

As Kelsea later tells People, Chase really helped Kelsea branch into acting. As she explains, “I’ve always called acting his world, and so whenever I was asking him questions about this opportunity, I was like, ‘What about this in your world?’ And he was like, ‘Hey, it’s just a world. I’m a part of it and now you’re a part of it.’”

And a few days after THAT, the couple rolls up at the People’s Choice Country Awards. Talk about booked and busy!

2024 people's choice country awards arrivals

Terry Wyatt//Getty Images

October 2024

Kelsea drops the music video for “First Rodeo,” which features her boyfriend—and according to her, he inspired the song as well!

During an interview with People, Kelsea talks about how Chase has helped support her writing. “I’m really proud of the art that he’s inspired,” she says. “And I’m really proud to be with someone who’s a truth-teller in his own art, too. And to be aligned in that way and to share parts of our relationship and that kind of stuff, so openly and willingly, is really beautiful.”

Watch the full video for “First Rodeo” here:

To close out the month, Chase and Kelsea dress as Grease’s lovebirds, Danny and Bad Sandy, at Heidi Klum’s iconic Heidiween party.

heidi klum's 23rd annual halloween party presented by butterfinger, mattel, and prime video at hard rock hotel new york arrivals

Noam Galai//Getty Images

Chase is so into his role that he gets on the floor and lets Kelsea step on him.

heidi klum's 23rd annual halloween party presented by butterfinger, mattel, and prime video at hard rock hotel new york arrivals

Noam Galai//Getty Images

November 2024

At Amazon’s Holiday Soirée, Kelsea exclusively shares with Cosmo the most thoughtful gift Chase has ever given her: a ring engraved with her dog’s name, Dibby, which he gave her for her 31st birthday.

Oh, and the most thoughtful gift Kelsea has ever given Chase? An original record by James Taylor with only two songs on it, including “Fire and Rain,” which Chase’s grandmother used to sing to him. I can’t with these two.

January 2025

Happy two-year anniversary to the lovebirds! In honor of the occasion, Chase posts some never-before-seen photos complete with a mushy caption:

February 2025

Chase and Kelsea stepped out for the 2025 Grammys being even more adorable than usual, if possible.

67th annual grammy awards show

Kevin Mazur//Getty Images

67th annual grammy awards show

John Shearer//Getty Images

67th annual grammy awards show

John Shearer//Getty Images

May 2025

Lots of cuteness at the Country Music Awards.

60th academy of country music awards arrivals

Christopher Polk//Getty Images

August 2025

After months with very few sightings (and a few rumors circulating on Reddit...), fans started to wonder if the two have gone their separate ways.

However! Chase seemingly clears up the rumors on August 4 by posting a picture of Kelsea's pup to his Instagram Story. Sooo...I guess they're doing fine?

kelsea ballerini dog

hichasestokes/Instagram

September 2025

Despite Chase celebrating Kelsea’s birthday on Instagram just two days earlier, sources claim Chase and Kelsea are over. Per People, “They’re two adults who gave it their all and tried to do everything they could to make it work, but ultimately couldn’t. It happens.”

Soon after, another insider spills more deets about the breakup to Us Weekly, claiming, “They had been arguing a lot recently, and their communication wasn’t great in the last month. They were both traveling so much and trying to juggle everything, and the arguments piled up.”

The source adds, “Although it’s been a few years, Kelsea is still coming out of a divorce and figuring out what she really wants, and she’s not in a place where she’s going to just settle. Chase understood that, but in the end, they realized they weren’t aligning the way they hoped.”

October 2025

Fans start to wonder whether Chase and Kelsea are actually done for good after Chase is spotted by a DeuxMoi tipster at the airport in Nashville (where Kelsea happens to own a home).

Soon after, another DeuxMoi source seemingly catches Kelsea Facetiming with Chase from the Keeneland race track in Kentucky. Iiiiinteresting.

November 2025

Days after they were reportedly spotted holding hands in Croatia, an Us Weekly insider confirms Chase and Kelsea “are giving their relationship another try,” adding, “There’s still a lot of love there, so they fell back into it very naturally.”

But then! Chase posts a series of Instagram Stories, where he writes, “Don’t believe the media. I’m blocked, I did nothing wrong. Sorry. I tried.”

He continues, “I’m sorry for those who believed in us. It is what it is. Onwards and upwards.”

January 2026

As expected, the breakup doesn’t last. Fans are not terribly surprised when Chase takes to Instagram on New Year Eve to announce he and Kelsea are back on.

“Something I’ve learned this year: don’t take advantage of the most beautiful things that in 33 years of life are fleeting,” he captions a series of romantic pics. Take accountability, learn from mistakes. Lean into love and say it often. 2026 my year of growth, my year of truth. Starting here, starting now. Happy new years ❤️”

Meanwhile, Kelsea writes on her own Instagram, “Messy year for the heart, messy year for the outside coming in, messy year for the way it became an out of our hands portrayal of it. But what I’ll say, and all I really care to share indefinitely with my personal life anymore, is that I really love love. I believe in it, I believe in him, and I believe in breaking patterns. Now go kiss your person and stop speculating.”

couple kissing at sunset

Instagram

February 2026

Kelsea shows up at the 2026 Grammys without Chase...but according to her, she and her BF are doing just fine.

After telling Entertainment Tonight that their brief split wasn’t as “dramatic” as it appeared, she says, “I love him so much. We’ve been together for quite a while now and done a lot of life together and he was with me getting ready today and he’ll be with me when we wrap. I love love and I believe it in it.”

Oh, and the next day, Chase’s ex Madelyn Cline takes to her Instagram Story to share a selfie of herself and Kelsea laughing together, which...is interesting!

two individuals with hair tied up closeup shot

Instagram

But then, less than a week later,TMZ announces the couple is done once again, with sources claiming “it’s completely over this time.”

April 2026

Less than two weeks after Kelsea makes an appearance on Today with Jenna & Sheinelleto describe the “three-day intensive in Dallas” with “nine hours of therapy every day” she did to get over Chase, a DeuxMoi tipster spots what looks like the two exes walking in NYC together.

Soon after, a source tells TMZ that Kelsea and Chase are “still on speaking terms but their on-again, off-again relationship is currently off, and they are NOT back together.”

More as we have it!!