Dress, Petal & Pup. Cardigan, Forever 21. Necklace, Berricle. Rings, Jenna’s own.
If Jenna Raine could turn back time and sign her own high school yearbook, she knows exactly what she’d write: “You’re not going to believe where you end up.”
Back then, Jenna was a wide-eyed girl from Westlake, Texas (a suburb of Dallas)—scribbling lyrics in the margins of her English homework, lamenting over confusing crushes and wondering what to wear to the school dance (sound familiar?). A far cry from the confident songstress we see on our FYPs today, she was just a talented student with a dream that felt out of reach.
“I always knew I wanted to do music, but living in Texas, I had no idea how that would actually work,” Jenna, now 21, shares.
Turns out, you don’t need to have roots in a major music hub like Nashville or New York City to make it big. Fast-forward a few years, and Jenna just played a sold-out show at the iconic House of Blues in Dallas—which, in a full-circle moment, happens to be the venue where she performed in her first-ever music recital at age 10.
Along the way, Jenna has built a playlist of songs that have helped millions of girls feel completely understood. “For people to feel real emotions from my music…that has always been my goal,” she says.
Her lyrics might sound like the wisdom of someone who’s seen it all, but really, they’re just the reflections of a girl figuring things out—one messy, complicated moment at a time. And that journey? It started in the halls of a tiny performing arts academy…and hasn’t stopped since.
So High School
From the second she hit the halls freshman year, Jenna was a booked and busy gal. She juggled traditional classes with daily voice, songwriting, piano and guitar lessons (two hours every day after school—no big deal) plus a handful of small acting and singing gigs.
“A lot of my high school experience was working on sets and doing my music,” Jenna says, adding that she often finished her homework on flights to and from shows. At the time, she was opening for the British singing duo Max & Harvey on tour, while acting in a few minor film roles.
From the outside, Jenna’s jet-setting, up-and-coming-artist lifestyle looked impressive. But on the inside, she often felt a little lost—wondering if her big break would ever come. “I was doing a bunch of work, but nothing was taking off from those opportunities. I didn’t have this one huge successful breakout moment or a song that blew up,” she recalls.
To make things more complicated, Jenna was also dealing with some major insecurities. “I really didn’t like how I looked,” she admits. “I stressed so much about what to wear. I couldn’t figure out my fashion sense, and I always worried about what my hair was like. I didn’t realize that it’s normal to feel awkward in high school.”
And then there was The Guy. (You know—the one who shows up at some point during your coming-of-age era and totally breaks your heart.)
“Freshman year, I really liked this boy, and I thought we were going to start dating. Then he told me he just wanted to be friends,” Jenna says. “That absolutely wrecked me. That was the saddest I’ve ever been.”
But like most things in Jenna’s life, it became fuel for her music. “Writing about it helped me know my worth and how I’m never going to rely on a boy to build me up,” she reveals.
It also marked the start of a bigger realization—that maybe her most personal moments were the ones that would resonate with people the most.
From homeroom to headliner
Everything changed during Jenna’s junior year when her breakup anthem “see you later” went viral on TikTok (a total dream come true). From there, her career—and her confidence— started to take shape.
In 2022, she dropped her first major label EP with Warner Records, followed by Chapters 1 and 2 of Big Dumb Heart—all while opening for Joshua Bassett, performing at the MTV VMAs Block Party and going viral (again) with her sunshine-y song “It Is What It Is.”
Jenna’s music has always radiated honest energy, but growing as both a person and an artist has made her even more comfortable being vulnerable. These days, she’s not afraid to show *all* the parts of herself—especially the ones that aren’t so bright and bubbly.
“I would see comments on ‘It Is What It Is’ about how I’m so happy and how my life was amazing. And it’s just not true,” Jenna says. “Don’t get me wrong, I love my life, but at the same time, I still go through hard things. I’m still a normal person and I still get sad. And I want my new music to reflect that.”
That new music is her latest EP, Only Started Growing, which dropped in April. And for this one, Jenna didn’t hold back. Whether she’s unpacking heartbreak (“Hitch Hiking”), empowerment (“Roses”) or uncertainty (“Who Am I”), her newest lyrics offer a deeper kind of honesty. “It’s the most ‘me’ EP I’ve ever released,” she says.
Currently in the midst of writing and recording her debut album, Jenna feels more confident than ever in her sound and writing process. “My inspiration for this record is early 2000s stuff like The Script, Sheryl Crow and Colbie Caillat. I want it to be very organic and band-driven,” she says. And while she can’t share all the details just yet, Jenna promises a headline tour is definitely on the horizon.
Top, Lioness. Pants, White Fox. Shoes, Skechers. Hoops and gold bracelet, Berricle. Beaded bracelet, Kylar Mack. Rings and studs, Jenna’s own.
Life lessons
Looking back on everything she’s learned since freshman year—from navigating crushes to fi nding her personal style (which she’s officially decided is just a baggy tee and jeans)—one thing’s for sure: You don’t need to have it all figured out.
“I was always so worried about what I was going to do with my future. Which, now that I think about it, is insane when you’re only 14,” Jenna laughs. “The truth is, you don’t need to know what you’re doing. Just chase your dreams and experiment and see what happens.”
When asked to reflect on how far she’s come, Jenna admits that her high school self probably wouldn’t even recognize her now (except for their shared undying love of Gilmore Girls and Italian food). “High school Jenna would absolutely freak out. I have to always remind myself that I’m literally living the life I prayed for,” she says.
Sure, Jenna still has big dreams on her vision board, but she’s already hit a major one: making music for girls that feels like the advice she always needed.
“I want to be a safe space for people, to help them as they’re growing up and figuring out who they are,” Jenna says. Her lyrics have undoubtedly become that source of comfort—and something tells us they’ll be showing up in yearbooks one day, too.
Hey, girl! Just to let you know, this originally ran in our August/September 2025 Issue. Read our print mag for *free* today when you click HERE!
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Photographed by Mike Azria.
Hair by George Fragkioudakis.
Makeup by Sophia Hutch.
Styled by Whitney Brielle.
