If "relatable human" were a mood board, at its center would be a giant picture of Jenna Raine. The 19-year-old singer-songwriter oozes an approachable, insta-BFF vibe that's impossible to ignore. She's the kind of person you meet and, five minutes later, it feels like you've been inseparable since kindergarten.

That vibe doesn't only work IRL—it hits you through the screen and speakers, too. Scroll through Jenna's TikTok and you'll feel ready to DM her your deepest secrets.

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By early 2020, Jenna was building a real following of people drawn to her authentic teen-girl content. But, tbh, that meant they were kind of missing the point...which, for Jenna, has always been her music.

When the pandemic hit, Jenna decided it was time to let her talent take center stage and embarked on her 100 Songs Challenge, inspired by her vocal coach. While just covering 100 songs would qualify as a challenge, Jenna's ambitious undertaking was to write 100 fully original songs and document her progress on TikTok.

Considering that 100 songs is, well, a lot of songs to write, it didn't take long for Jenna to start reaching out to her followers for inspo—and for one of those comment suggestions ("right person, wrong time") to inspire what would become her breakout, 100-million-streams-and-counting hit, "see you later (ten years)."

Of course, not *every* song Jenna wrote during the challenge was a smash. At least one made her cringe too much to share it.

"It was called 'Jackpot' and I hated it so much," she says, laughing. "I remember getting up from the piano and being like, 'That was the worst song I've ever written. I'm going to go get chicken now.'"

Jenna may have drowned her embarrassment in a plate of Raising Cane's tenders, but that's pretty much the extent of the impact writing her "worst song ever" had on her day.

"You have to write bad songs to get to the good ones—it's just inevitable," she reflects. "If I hadn't written 'Jackpot,' I wouldn't have gotten to 'see you later.'"

There's a reason Jenna has the perspective of an industry veteran. Her viral TikToks may have recently landed her on your screens, but the Texas native has been quietly building a music career for, well, most of her life.

She started taking piano lessons in preschool and, by the time she was 10, was chosen to be part of a girl group called L2M. The band broke up after four years, but Jenna kept working, honing her songwriting skills and dabbling in acting (see 2017's YouTube Red original Hyperlinked).

Somehow, in the midst of all that, she's managed to maintain a pretty normal teenage existence, complete with typically all-consuming high school moments like friendship reckonings and first love. Those are the stories Jenna explores on Big Dumb Heart, Chapter 1 (the EP came out on May 5) and now on Big Dumb Heart, Chapter 2 (out today—stream it HERE!).

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Her genuine, vulnerable energy shines through each of her songs. We dare you to listen to "She's There" (inspired by Jenna's realization that some of her former friendships weren't right for her) and not feel deeply seen.

"Back in high school, I had no one there for me," Jenna says of her old friend group, where she often felt taken advantage of for her empathetic nature. "I poured everything into other people and never got filled back up. I wanted to cry all the time."

Ultimately, Jenna realized the solution to her hurt was to create some much-needed distance between her and her crew—even though it took strength.

"It was really, really hard, but I started to love spending time by myself," Jenna remembers. "I learned to be comfortable in my own skin, to feel like I had a voice and to not have to shut up when people were upsetting me. And that was huge."

Once Jenna started surrounding herself with people who put as much into friendships as she did, even her natural tendency to be "everyone's therapist" (a role she describes as "the most exhausting job in a friend group") stopped draining her.

"I genuinely enjoy it now, because I have people who are there for me, too," she says of the inner circle she's created since letting go of her other less-than-healthy friendships.

And that experience of learning to love herself helped lead her to the breakout hit of her personal life—falling in love with her boyfriend of three years, Harrison, the main source of inspiration for "see you later" after she got that "right person, wrong time" prompt from her follower.

Though sparks flew during their initial meet-up a few years back, the couple never quite connected. But when their paths crossed again, fate decided it was finally the right time for Jenna and Harrison.

"As soon as we reconnected, he was like, 'Whoa, wait, you've definitely found yourself,' and the same went for him," she says of their reunion.

Though they're long-distance for now (with Harrison in college in Texas and Jenna recording music in Los Angeles), they always make the effort to show up and support one another.

"This spring, I had three Texas shows opening up for Joshua Bassett, and Harrison drove to every single one of them," Jenna gushes. "And it was three nights in a row—and each night was like a three-hour drive. And he had school. So he'd go to class, then drive to the show, then drive home and wake up for school, then drive to the next show, then drive home." (Goals? We think yes.)

While Big Dumb Heart, Chapter 1 covers Jenna's emotional journey from 15 to 18 ("how my heart got me a little broken at times," she reveals), Chapter 2 is inspired by the beauty of love, plus the upsides of being so empathetic and authentic.

"Yes, there are times when you need to protect yourself and put a wall up and not let in every single person that you meet," she says. "But there's so much light that comes from having a 'big dumb' heart. It has brought me so much love and joy."

With two EPs laying out her past and present for the world, we can't help but ask Jenna what the future holds for her. There are the obvious things like a tour (which she says is in the works) and maybe even future chapters in the Big Dumb Heart saga, but her career is exploding so fast that it's hard to pinpoint what's coming next.

No matter what her life/love/friendships/career has in store for her, Jenna knows she'll keep facing it all with her open heart.

"I want to continue telling my story in the best way possible," she says. We'll just be busy refreshing her Spotify until then.

CLICK HERE to stream Big Dumb Heart, Chapter 2 rn!

Hey, girl! Just wanted to let you know that this story originally ran in our August/September 2023 issue. Want more? Read the print mag for free *today* when you click HERE.

Credits: Photographed by Mike Azria. Styled by Lo VonRumpf. Hair by George Fragkioudakis. Makeup by Sophia Hutch. Story edited for digital coverage by Ava Slocum.

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