My best friend Niha knew everything when we were young. She knew Pinkberry was chicer than ice cream, because it was tart, and because you could only get it by taking a two-hour bus from our hometown to New York City. When she won “best dressed” in high school, she knew to show up to the yearbook photo wearing a trash bag. And she knew the song “White Houses” by Vanessa Carlton. When she put a stanza about a boy in a red shirt as her AIM away message in 8th grade, I immediately scanned the AZLyrics page for another verse, typed it out in pink text, and added it to my own profile. I didn’t realize that the lyrics “My first time, hard to explain, rush of blood, and a little bit of pain” were about losing your virginity. But I wanted to experience whatever angst and drama it was that Carlton (and Niha) knew about.

The word “blood” ended up being a problem for Carlton. Youth media had a specific fixation on virginity and chastity just then. Following the HIV/AIDs crisis in the 1980s, sex education increased in the 1990s and 2000s, fueling backlash from evangelical Christian groups hell-bent on preaching abstinence. In 2001, President George W. Bush allocated federal funding to some of these organizations. Disney Channel stars wore purity rings. On Fearless track “Fifteen,” released in 2008, Taylor Swift explains that she has bigger dreams than just having a high school boyfriend. Still, when she sings about her best friend’s first experience of sex, she laments, “Abigail gave everything she had/To a boy who changed his mind/And we both cried.” At the 2004 Super Bowl halftime show, Justin Timberlake ripped off part of Janet Jackson’s blouse, and she faced the backlash—the kind of repercussion for perceived promiscuity that’s always fallen more harshly on Black women. MTV amped up its censorship of anything that could be deemed indecent, like a woman’s bellybutton or breast, or maybe the workings of her inner world. And so, when Carlton released “White Houses,” the lead single from her second album, Harmonium, it was soon banned on MTV because it included a stanza about a woman bleeding when she lost her virginity.

The stakes were high for Carlton. Her debut, 2002’s Be Not Nobody, hit No. 5 on the Billboard charts, and she and her label hoped to make her follow-up just as successful. The debut’s popularity was due in large part to “A Thousand Miles,” a catchy, heady orchestral pop tune about unrequited love. That song also hit No. 5 on the Billboard Hot 100, becoming a defining song of early-2000s pop. Terry Crews sang along to it in 2004’s White Chicks, and it’s since been widely sampled: by Cam’ron, and by Rico Nasty, and in Yungeen Ace, Whoppa Wit Da Choppa, Spinabenz, and FastMoney Goon’s viral 2021 track “Who I Smoke.”

Since the late 1990s, pop radio had been dominated by stars like Britney Spears and Christina Aguilera who danced, wore latex, and sang confident, high-octane pop songs, often written by a team of pro hitmakers. Carlton has recalled that when she was starting out, label executives took note of her ballet training, in case they wanted to push her down that route. But, as the songs on Be Not Nobody took shape, it became clear she was a different kind of musician: She had been a student at Columbia when she dropped out to pursue music. She cited Mozart and Chopin as influences. She wrote her own songs. The music video for “A Thousand Miles” featured her playing the piano across Los Angeles, a decision that underscored her relationship with her instrument.

Carlton and peers like Michelle Branch and Avril Lavigne were quickly labeled by the media as “anti-Britney” musicians, women whose work supposedly had more depth. They were less sexually deviant. More intelligent. More empowered. Maybe they would have a more positive impact on young girls. It’s a fallacy that crumbles the second you consider Spears’ “Lucky,” one of the most profound and lonely pop songs ever written. And when you remember that Britney, wearing jeans and a long-sleeved blouse, was asked by interviewers, “Where are your clothes?” And when you realize that the principals who gave us detention for wearing Britney-inspired belly shirts that “distracted male teachers” were sexualizing our 8-year-old bodies themselves.

It was a classic Madonna/whore construct. There’s a level of privilege in being read as innocent, but the expectation still proved restrictive for Carlton. When she released “White Houses,” a coming-of-age song about a girl losing her virginity and her friendships, she was suddenly singing about sex, desire, regret, and betrayal. Girls like her, girls who were valued for their purity, weren’t supposed to experience those things. “I think I was viewed as much more of a sweet girl,” Carlton said in a 2011 interview with The Huffington Post. “Not that that’s not a sweet song, but it’s a very realistic song. It’s a serious song with a serious and multidimensional story. I’m not sure why it [wasn’t] just accepted for what it was and it had to be censored in certain ways.” There was drama behind the scenes, too: Carlton wanted to move on from working with Ron Fair, who’d produced her first record, and instead decided to bring on her boyfriend, Third Eye Blind’s Stephen Jenkins. The decision led to tension with her label, whom she says didn’t adequately promote the record. She also found herself in a controlling environment with Jenkins, who, it turned out, didn’t actually have much production experience.

Harmonium, which debuted and peaked at No. 33 on the album chart, was not the smash success that Carlon’s first album was. In the mainstream zeitgeist, she might be remembered as a one-hit wonder for “A Thousand Miles.” But “White Houses” is the truly singular song in her oeuvre and in early 2000s pop more generally. It was written as Carlton was challenging the media’s expectations of who she was and what young female artists could feel; there’s a sense of expansiveness to the song, an ability to let many narratives and emotional truths exist at once. It’s an inconvenient, messy story about a woman who loves with a naive freedom that is just beginning to tip into jaded caution, who makes mistakes she never resolves, who is transitioning from the innocence of childhood to the complicated self-knowledge of adulthood.

“White Houses” depicts the arc of a summer in which the protagonist moves into an idyllic new home, quickly builds a tight-knit friend group, falls in love, loses her virginity, and experiences her first heartbreak. Love tumbles into heartache which leads to severed friendships that in turn leave her feeling alienated from herself. Carlton scaffolds the story through vivid imagery that progresses from eager to disillusioned. Propelled by a crystalline piano note that sounds simultaneously like a heartbeat and clock counting the moments till the bubble bursts, she details a series of potent memories: “Beer through the nose on an inside joke,” the smell of gasoline on the cracked leather seats of a lover’s car, and, eventually, the sun setting on the white houses where it all happened. She delivers those initial awestruck memories in a falsetto so openhearted, so earnest, that you feel your heart breaking for her in real time.

Just as you’re immersed in the details of her world, Carlton widens the scope: “We were all in love and we all got hurt”; “These silly little wounds will never mend.” These maxims could sound overdramatic, but because the earlier imagery is so rooted, they come across as earned and serious, like bits of inherited wisdom. “White Houses” feels both like a story your best friend told you and also like a state of the union on early womanhood writ large: The intensity with which you rush into relationships when you’ve never had to live with the pain of them ending. The unwavering allegiance you feel to a scene or a perspective as a teenager, and the anger that swells when anyone violates its terms. The competitiveness and jealousy that seeps into female friendships in a society that constantly compares women to each other. The way trauma leaves you feeling so alienated from your body that sometimes the only solution you can imagine is to leave everything behind and start over as someone new.

“White Houses” loosens the compact pop structure of “A Thousand Miles” a bit, feeling less neatly packaged and more exploratory. Still, Carlton uses her preexisting arsenal of tools—piano, strings, drums, an acoustic guitar melody played by Lindsey Buckingham—to build a sense of cinematic grandiosity. The percussion gallops, the strings pirouette, and Buckingham’s guitar shimmers like sunlight on a lake. The song seems to shudder as Carlton sings the stanza about losing one’s virginity: Suddenly it’s just her, the piano, and the strings. It’s an echo of the similarly sparse beginning, this time imbued with the weight of all that’s happened to her. Much as she might want to, she can’t go back to who she was.

The characters of “White Houses” were a product of their time, when young women often heard that the experience of losing their virginity would fundamentally change them, typically for the worse. A woman who had sex once, the warning went, had taken the first step toward sleeping with multiple men, a choice that would mark her as impure and impulsive, easy to “get” and therefore easy to discard, no longer in possession of the one thing that men valued from her. Those ideas had broader implications: that your body and your personhood should belong to someone else first. That it is your job to make yourself pleasing to men. That, ultimately, this work should give your life its meaning, more than art, more than family, more than friendship.

Where would the girl from “White Houses” be now? She could move to another city, read some Judith Butler, date a man who doesn’t own a bed frame, and come to understand that nothing about you fundamentally changes just because you decide to sleep with someone or not. But sometimes, those bigger ideas linger, influencing your self-perception and your sense of priorities, long after you’ve intellectually let them go. A few years ago, when I was stuck in a tortuous and addictive relationship, Niha searched “how to get your friend out of a relationship” on TikTok and called every day to share her findings. The vastness of her love—patient, nonjudgmental—felt like more than I could ever repay. Eventually, between one false breakup and another rocky reconciliation, I stopped filling her in, texted one-word responses, missed her graduate school graduation ceremony entirely.

She ultimately forgave me for my distance and lies of omission, but it was startling to encounter the version of myself who would put her in that position. This is one of the tragedies at the heart of “White Houses”—not just the pain of young love gone sour, but the regret for the people you’ve hurt or taken for granted in the scramble to make it work. It’s the loss of virginity that represents the emotional turning point in “White Houses.” But when Carlton sings, “We gave each other up so easily,” she’s not just mourning romantic heartbreak, but her protagonist’s whole world that summer—the kinship she and her friends jeopardized in the name of love that was supposed to make them feel complete.

“He’s my first mistake,” Carlton admits at the turning point of the song. When you’re a teenager whose heart has been broken for the first time, it does feel like that. Who will want you now? Why did you waste your time? But when you’ve lived through it more than once, you realize the mistake is never loving another person. It’s what you were told you should give up in the pursuit, and the extent to which you were willing to listen.

“White Houses” is full of harsh realizations, but nevertheless I find it empowering. Not in the way a Meghan Trainor song tries to be—it’s more subtle than that. Though it was never a smash hit, you hear the song’s brutal honesty, self-examination, and nuanced storytelling in the work of today’s poet laureates of young womanhood. It’s there when Lorde admits to “blowing all my friendships to sit in hell with you,” when Olivia Rodrigo asks when she will “stop being wise beyond my years and just start being wise,” when SZA acknowledges she’s “lonely enough to let you treat me like this.” The song is also a favorite of screenwriter Lena Dunham, and it feels like it could soundtrack almost any scene of Girls, whether the characters are falling in love with each others’ exes and hating themselves for it or realizing their relationships never truly worked the way they’d wanted.

“White Houses” can be a balm that tells you all the feelings you’re most ashamed of are in fact quite ordinary. But it’s also a provocation: to think outside of the flattened archetypes that pop culture offers to women. To take yourself so seriously, to see yourself so fully, that you can’t possibly lie anymore.