Kelsea Ballerini’s Wild, Wild Year

Kelsea Ballerini is having a low-key breakfast in a secluded corner of her hotel restaurant when she is interrupted by two fans. They’re both middle-aged white women, in town for business and also staying at the Brooklyn spot where Ballerini has been spending the week. “You got on the elevator with me yesterday and when you got off everybody was like, ‘Didn’t you know who that was?’” the first woman says, a rolling briefcase by her side. “I’m like, ‘Oh my gosh. She was gorgeous.’”

“You’re here for a conference,” Ballerini beams back at her. “I eavesdropped.”

The second woman is more familiar with Ballerini: Her 9-year-old daughter is a fan. “Everyone tells my daughter that she looks like you,” she says. “It’s like the highest compliment. Your new song is her absolute favorite.” Ballerini gets up to take a picture and offer the 9-year-old some proof that her mom is, in fact, cool. Both women, satisfied with the encounter, effusively thank the singer and apologize for interrupting. “You’re so pretty,” Woman Two says on her way out. “You’re so much prettier in person.”

When they’re out of earshot, Ballerini laughs. “I get that all the time,” she says. A few years ago, she was having a girls night in Nashville, where she lives, chilling on a friend’s balcony when they spotted a rager across the street and decided to crash. One of the partygoers noticed her immediately. “She said, ‘Are you Kelsea?’ and I said, ‘Yes, nice to meet you.’ Then her friend comes up: ‘That’s not Kelsea. I’ve met Kelsea. She’s much prettier,’” Ballerini says. “That was humbling.”

For the record: Ballerini did get some light glam done right before our breakfast date. Across four megawatt studio albums, TV hosting gigs, and beauty deals with brands like Covergirl and Pantene, she’s the rare country star to achieve sparkling pop stardom without ever leaving the genre. But lately, Ballerini is more comfortable letting the world see her as is. In February, she notched a career breakthrough with Rolling Up the Welcome Mat, a stripped-back account of the end of a marriage following her own divorce in 2022. On Instagram, she breaks up the glamor shots with candid photo dumps that let fans into her new relationship with Outer Banks star Chase Stokes and life on the road — she’s spent most of the past year on tour. “It’s been wild,” she says of her 2023. “Wild, but it’s also been really good.”

Last month, she rang in her 30th birthday by attending the MTV Video Music Awards. She walked the red carpet with Stokes; performed her devastating song “Penthouse”; danced next to seatmate Lil Nas X; and accepted birthday wishes from Taylor Swift. And then she left. “Oh, I left so early,” she says with glee. “I went to dinner with my mom and my friends. I literally feel like there was not one more drop of my 20s I could have wrung out. I’m ready to be a grown-up now. That’s so hot to me.”

So far, being in her 30s suits Ballerini. “Your 20s are for self-discovery, for f*cking up, for trying your best, for succeeding in some ways and for failing in others,” she says. “And I did that. I did all of that and I stand by it. I experienced so much that I was lucky to get to do in my 20s — to travel the world like I’ve gotten to, to have experiences with people that I have. I don’t take it for granted, for sure. But I also feel very at peace.”

For Ballerini, all that f*cking up and finding herself happened with a lot of people watching. An only child from just outside of Knoxville, Tennessee, she traded dance shoes for the guitar at age 13, moved to Nashville at 15, and by 19 had signed a record deal. When her first single, “Love Me Like You Mean It,” hit No. 1 at country radio in 2014, she was the first female solo artist to do so with their debut since Carrie Underwood nearly a decade prior. And when Ballerini wasn’t setting other records with hits like “Peter Pan” and “Dibs,” she was lighting up red carpets as one half of a country It Couple. She was married to fellow singer-songwriter Morgan Evans from 2017 to 2022; their divorce was finalized almost exactly one year ago.

“I have less famous friends than I ever have. This is so cringe to say out loud, but it’s just the truth.”

“This time last year, my life felt very out of control. A bit messy. I just felt in the weeds in a lot of things.” she says. She considers her words carefully. “I can truly, from my guts, say I regret literally nothing. I really don’t.”

It’s the only time she seems a little unsure of what to say. In conversation, Ballerini is absurdly easy to talk to. With her big, expressive green eyes, she’s the kind of person you immediately want to confess all your secrets to, the kind of person who seems like she makes friends everywhere she goes. She and I first met late last year when her publicist suggested the two of us get coffee when she was in town. We met in the East Village around 3 p.m. and Ballerini immediately suggested we get wine instead. Today she rolls up to the table in a black turtleneck with her hair pulled into a bun and a Starbucks cup in hand. I hear her before she approaches me from behind: “Oh hey friend!”

And anyway, if there’s something you want to know about her personal life, it’s all in the music. Last September, while on a headlining tour supporting her 2022 album, Subject to Change, she started writing again. “Normally I can’t write on tour, but this was like, ‘I got to write about this or else I’m going to be not in a great place,’” she says. First came “Blindsided,” a soul-wrencher about a partner that ignores the signs of a relationship in turmoil: “We had to get drunk to ever really talk,” she sings. “I told you what I needed, didn’t have to read my mind.”

In January, she wrote “Just Married,” about when newlywed optimism confronts real life. (“Long distance texts, make-up-for-time sex / Tired of asking when I’ll see you next.”) From her living room, she fired off a voice-memo demo to her manager. “I said, ‘I think this is the best song I’ve ever written,’” Ballerini recalls. “He listened to it like, ‘Would you ever put this out?’ And I was like, ‘I think I have a whole EP.’”

Rolling Up the Welcome Mat dropped with little warning one month later alongside a 20-minute short film, also written and co-directed by Ballerini. She wanted the songs to speak for themselves, so she only did one interview for it, on Alex Cooper’s Call Her Daddy podcast. The interview blew up anyway: She talked about feeling “really used” by Evans’ post-divorce song, “Over for You,” and spoke about legal bumps. He fired back on Instagram, saying it was “really sad” to see her “saying things that aren’t reality.” Headlines swirled. “I thought, ‘Everything is so looked-at right now in this situation that I’m in, I don’t really want to make it a spectacle,’” Ballerini says now. “Which in hindsight is laughable because it became such a spectacle, but that was never my intention.” Cooper tells me it was one of the show’s most watched episodes. “When I was listening to Kelsea, it felt like I was in the room with one of my best friends and I truly believe that’s how the audience felt too,” says Cooper. “I think so many women are not only able to see themselves in Kelsea’s story, but are also able to look to her as an example of grace, strength.”

“The people-pleaser in me still has a hard time when there’s very loud hate coming out of things. But I’m sleeping better than I ever have.”

One of the perks of spectacle, though, is the opportunity to reintroduce yourself. In addition to getting some of the best reviews of her career for Welcome Mat, within a month Ballerini also booked Saturday Night Live for the first time, a gig she’d begged to land for Subject to Change the year prior.

“I’ve always had this complex that people don't think of me as a credible artist, that people just are like, ‘Oh, she got signed to a label and she had a number one right off the bat, she’s blond, she’s glittery, she posts stuff, she’s this personality,’” she says. “That’s the thing that I care about the actual least. I have fun with all of that, but I’ve never cut a song I didn’t write. I never will.” Welcome Mat, she continues, “has made people think of me in more of a rooted, grounded, ‘I’m a real artist’ kind of way. And maybe that’s something that I shouldn’t have cared about. But I do care. Maybe that’s just a notch in my belt that I had to get for myself to feel validated. But I do feel that now.”

Here’s another lesson Ballerini picked up in her 20s: “Care more about less,” she explains. “Then you’re really investing in the things that you care about, and having better, more fulfilling, healthier relationships. Less of them, but better.”

Prior to the VMAs, she kicked off her birthday celebrations with a week in St. John with her closest girlfriends. They’re people she’s known since her teens — her elementary school BFF, her college roommate, the people she came up with in Nashville. “My ride-or-dies that have no skin in the game for me in my career,” as she puts it.

“I have less famous friends than I ever have,” Ballerini says. “This is so cringe to say out loud, but it’s just the truth. When I first started and was in the rooms with people that I used to have posters of on my wall, I was so starry eyed and very magnetized to it. There was definitely part of my drive that [wanted to] be in one of those rooms. And I would like to think that’s just human nature, but I hate that that was part of my drive. Because it’s not pure. For a while I was very interested in, ‘Oh yeah, hanging out with this person today.’ It just did not feed my soul at all. I just ended up having some disappointments and shifted into my real life again.”

“I have spent so much of my life contorting myself to be palatable to everyone. I thought that made me a good woman. I thought that made me a good artist.”

Not that she’s lonely in Hollywood. “I’m very friendly with a lot of people,” she says. “And there are, I would think, a good-sized group of people that if they called me, I would pick up and vice versa, if we needed each other.”

On a recent trip to the Venice Film Festival, she hit it off with Riverdale actor Lili Reinhart, both barefoot in the bathroom of a black-tie affair. “You can immediately feel a sense of how down to earth she is, and that’s something I always gravitate to,” Reinhart tells me. “We were at a dinner together and snuck away to the bathroom to talk about how we wanted to leave and go back to the hotel. We bonded over our discomfort in these situations where you’re surrounded by people who are buying everyone shots and trying to impress you with their connections and money. It’s easy to get caught up in that world, but Kelsea is definitely not won over by any kind of schmoozing.” Adds Reinhart’s former co-star Camila Mendes, who was also on the trip, “There's a lot of fake humility in this industry, but Kelsea's humility is the genuine kind. She's the most grounded, unpretentious person who works really hard and cares deeply about making music. I feel really lucky that we forged such a strong connection and I'm happy I get to call her my friend.”

It’s a little funny, then, that her boyfriend happens to be one of TV’s most beloved heartthrobs. Fancy dinners and parties are an occupational hazard. But last year, Ballerini was just a single girl, shooting her shot in the DMs.

“I was at a bar in Nashville with some friends from Charleston [where Outer Banks films], and they were like, ‘What about Chase?’” she says. So she followed him on Instagram. He followed her back. And then… “I was just like, ‘Why am I waiting for this guy to reach out to me? This is 2022.’” Ballerini sent him a flirty DM, which she posted on main last month to celebrate Stokes’ 31st birthday. The message — “hiii chase stokes” — was maybe less interesting than the time she sent it: 1:07 a.m. “Bro, I know,” Ballerini says, laughing. “Listen, I was living my best life. I have no shame in that game.”

“He is the first person I’ve been in a relationship with that I feel like is not my complete opposite.”

They planned their first date for a few weeks later when they were both going to be in Los Angeles. It was a three-day trip for Ballerini, and the date was set for day two. “Day one I was playing a birthday party for a friend of mine, but I got there and was like, ‘It’s kind of crazy that we’re finally in the same town and I’m not seeing you today,’” she recalls. “He was like, ‘Drop your pin.’ He just showed up at this party and yeah, it was great.”

From there, it was on. “I really did [know] as soon as I met him,” she says. “And maybe that sounds like I’ve learned zero things, but I’ve always been a heart-first girl” — her last headlining tour was literally called the Heartfirst Tour — “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.”

I ask if she was hesitant to share her new relationship with the whole world coming off a public divorce. The answer is slightly complicated. For Ballerini, it is hard to untangle what it’s like to get divorced from what it’s like to get divorced as a country singer. Splitting from Evans, she says, was “making a lot of conservative Karens very upset.” She’d get comments on social media about how she didn’t try hard enough, that she gave up on being a good wife. “That scared me.” But it prompted a lot of soul-searching about how she wants to live and work in the spotlight.

“I have spent so much of my life contorting myself to be palatable for everyone. I thought that made me a good woman. I thought that made me a good artist. However, it does not make me a good person,” Ballerini says. “I care way more about being able to sleep at night knowing that I’m showing up for myself and what I believe in and the things that make my heart beat. And I’m not meant for everyone. The people-pleaser in me still has a really hard time when there’s very loud hate coming out of things. But I’m sleeping better than I ever have.”

“This time last year my life felt very out of control.”

Breaking down taboos around divorce is important to her, too. “I knew that there are also a lot of girls in their 20s that got married really young that are probably experiencing similar feelings,” she says. “And I also watched my parents get divorced when I was 12, and I was very interested in normalizing that conversation in my own way. Taking any kind of stigma or ick around that topic away, especially for young women, is really beautiful.”

To do all that, she has to celebrate her relationship like any other millennial in love: with cutesy selfies and astrological analysis. (They’re both Virgos.) “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,” she says of Stokes. “He is the first person I’ve been in a relationship with that I feel like is not my complete opposite.”

Last November, Ballerini bought her dream house in Nashville. The post-divorce pad previously belonged to fellow country star Kacey Musgraves, who bought it in 2020 to be her post-divorce pad. Ballerini’s been renovating it room by room, with such highlights as a secret lair to drink tequila with her girlfriends that she’s calling the “chicken coop.” “It’s like my 1920s little Narnia cottage,” she says. “It has so much personality, and it’s mine.” Over the past year, she’s spent, by her estimate, 11 days in it. “I’m ready to hibernate.”

But there are a few things she has to cross off her list first: a sold-out hometown show at Knoxville’s Thompson-Boling Arena, an intensive three-day therapy retreat she’s taking as a “pulse check” following the whirlwind of her last few months. “Not only has my outward world changed a whole lot, and I’m still adapting to that, but my interpersonal world has changed dramatically,” she says. “And although it’s all positive and what I wanted and better than I could have imagined, it doesn’t mean that it’s not massive changes.”

“I can truly, from my guts, say I regret literally nothing. I really don’t.”

Then she’s done for the year. But “done” for Ballerini doesn’t exactly mean vacation. She’ll probably be plotting her next goals and how to achieve them. There’s acting, which she’s been wanting to try but has been putting off for the fear of “sucking.” She wants to sell out a full-on arena tour, one where she comes out in a hydraulic lift like a proper pop star. “And I really want to win a Grammy. I do.”

She’s got a writing retreat planned in the coming weeks where she’ll be “coming in hot,” she says. “With Welcome Mat and the details that I put in that, it couldn’t have been about anyone else. It was so jarringly mine. I need that same level of, ‘This was my idea, front to back.’” But Ballerini admits she’s still figuring out how to write about her new reality.

“I have a literal song called ‘I Hate Love Songs.’ I’m just not good at it. It’s so much easier for me to write about hardships and turmoil,” she says. “I’m trying to figure out what that sounds like now at 30 and happy.”

Top image credits: Cecilie Bahnsen top, Oséree bottoms, Serratelli hat c/o Boot Barn, Giuseppe Zanotti boots

Photographs by Ryan Pfluger

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