“They say modern love’s a cruel endeavor,” Olivia Rodrigo sings on “u + me = <3,” a lush, desperate new song from her third album, “You Seem Pretty Sad for a Girl So in Love.” She adds, “And to that I say, ‘Fuck it, whatever.’ ” Insouciance has always been Rodrigo’s abiding philosophy when it comes to romance. If her discography has a single repeating theme, it’s that love is ruinous, a surefire path to acting like a ding-dong. Once again, Rodrigo shrugs off concern. What else would she do—stay home?

Rodrigo began her career as a child actor. By age seven, she’d had her first role, in an Old Navy commercial; by thirteen, she was starring in her own Disney Channel series—but she didn’t become a superstar until 2021, with the release of “Drivers License,” an indignant, slow-burning anthem about the humiliation of desiring someone who betrayed you. Her first two albums, which contain a mix of moody, stricken ballads and springy, punkish romps, remind me of Taylor Swift and Avril Lavigne, with a hint of Ashlee Simpson thrown in: poppy, highly confessional, sometimes slapsticky songs about how love pushes even the best of us to the precipice of insanity. Rodrigo’s always had cool taste—she collaborated with David Byrne; Blondie introduced one of her performances on “S.N.L.”; Robert Smith, of the Cure, is a guest vocalist on a new song, “What’s Wrong with Me”—but she’s just beginning to figure out how to merge her countercultural influences with her Disney pedigree.

On “You Seem Pretty Sad for a Girl So in Love,” Rodrigo, who is twenty-three, is inching away from frisky, impish pop-punk and leaning more toward New Wave, with its melodic synthesizers and velvety yearning. (There’s also a good dose of angsty nineties alt-rock here, including tracks that sound inspired by Weezer, the Smashing Pumpkins, and the Breeders.) Rodrigo has a disarmingly powerful soprano, and she’s a charming, determined performer. I still recall, with a mix of horror and reverence, a viral clip of her tumbling into an open hole in the stage during the “Guts” tour, bouncing back out, and proceeding to finish the show.

The first side of “You Seem Pretty Sad for a Girl So in Love” is about the euphoria and terror of new love. But the back half is a heady object lesson in the limits of partnership—how even the right person can’t fully quell whatever torment lurks in the recesses of one’s consciousness. “I know everybody changes, but I hope that we don’t,” Rodrigo wails on the chorus of “u + me = <3.” It’s a lyric destined to make elders in the room grimace. Change is inexorable; better to hope that you evolve in compatible ways.

That idea—love as a failed panacea—reaches its apotheosis on “The Cure,” a tense and melancholy song about hoping a new relationship might liberate you from your worst impulses. She sings:

Used to play a game in my head when I’d date a guy

Tally up the girls that he fucked ’til I start to cry

Envy and uncertainty are not new terrain for Rodrigo, but I was nonetheless struck by the grimness of the line. The track recalls the drama and mournfulness of two songs by the Smashing Pumpkins: “Disarm” (about abuse and resentment) and “Tonight, Tonight” (about trying to outrun yourself). Rodrigo’s fans are young—some very young—and her music is perky, composed, and telegenic in a way that can distract from how much darkness and loathing lurk within it. Now she is perhaps exactly at the age in which a person realizes how often those things come to coexist.

In May, Rodrigo performed at a Spotify event in Barcelona, wearing a puffy floral top and matching bloomers, an ensemble that resembled a baby-doll dress, or, more specifically, the kind of dainty frock a Victorian toddler might have donned to waddle the gardens under her nanny’s parasol. It led to some pearl-clutching about Rodrigo’s supposed self-infantilization—a concession, perhaps, to a culture of predation on young women. Rodrigo eventually countered that her detractors were blaming the wrong person. “I just think it just shows how we normalize pedophilia in our culture,” she told the Times. “It’s just this rhetoric that we’re fed as girls since we’re so little, which is like, don’t wear that because then a man is going to sexualize your body and it’s your fault.”

Rodrigo said that the outfit was inspired by nineties alt-rock icons such as Courtney Love and Kathleen Hanna, who often wore baby-doll dresses onstage, though back then the styling was generally gnarlier (ripped tights, unwashed hair, smeared makeup), which made the whole look feel cheeky and subversive. Hanna, who founded Bikini Kill—and, by extension, is a primary architect of riot grrrl, a subgenre of punk that centers feminist rage—often weaponized fashion, performing with the word “slut” written across her belly, or in hot pants with a little bush peeking out, or in a tomato-red go-go dress that featured the phrase “KILL ME” in ironed-on white letters. Even more pointedly, Hanna occasionally put on a Girl Scout uniform, a caustic homage to being sexualized as a young girl; Love once wrote “WITCH” on her arm in red lipstick while wearing a white baby-doll dress with a stuffed doll dangling from the hip.

I came of age in the late nineteen-nineties, and worshipped Love and Hanna (also Kim Gordon, Kim and Kelley Deal, Juliana Hatfield, PJ Harvey, and Björk). Part of what fascinated me about their presentation was not only their refusal to kowtow to male desire, which for decades had a stranglehold on rock aesthetics, but a concomitant disavowal of commercialism. For Hanna and her cohort, the idea was not so much to court popular attention but to repel it.

Unlike her riot-grrrl idols, I would not describe Rodrigo as radical, exactly, but she is not apolitical. In June of 2022, during Rodrigo’s Glastonbury début, a day after the Supreme Court overturned Roe v. Wade, she and Lily Allen performed Allen’s song “Fuck You.” Rodrigo dedicated the performance to the five Justices who voted in favor of the decision, and called them out by name. “They truly don’t give a shit about freedom,” she said. (On tour the following year, she partnered with the National Network of Abortion Funds.) Last fall, when the Trump Administration used “All-American Bitch,” a song from “Guts,” in a video valorizing ICE agents, Rodrigo reacted with outrage, calling the footage “awful and barbaric and cruel.”

In general, the rub with pop music is that it almost invariably babies and defangs its practitioners; the best pop songs are about big, dumb, adolescent feelings (an overwhelming crush, a cataclysmic breakup, getting zooted and having a blast). It’s never been the right medium for nuance or rebellion or cataloguing the endless, wretched banalities that actually make up an adult life; as such, it’s not particularly easy for pop stars to age or evolve. This is doubly true for women, who are more likely to get mired in the quicksand between coquettish ingénue and grande dame, and who are given far less leeway when it comes to the rules of growing up.

“You Seem Pretty Sad for a Girl So in Love” is germane to Rodrigo’s age, transitional in the way one’s early twenties can feel provisional and wildly unpredictable. On “Drop Dead,” the opening track, Rodrigo toggles between girlish hopes (there are lyrical nods to chewing gum and holding hands) and more mature wants (“And then maybe we could make, make out / Clothes off and fall to the ground”). Yet, by the end of the record, Rodrigo sounds less like a love-struck teen. On “Expectations,” the album’s eighties-inspired penultimate song, she sings about learning how to temper her hopes and dreams, or at least to stop looking for love in all the wrong places:

So I hit the new year like a single girl at a Vegas bar

Rocking my mini dress with a vodka cran and an open heart

Yeah, I’ve got hope, yeah, I’ve got drive, I will not lose my faith

Don’t think my future husband’s at this bar in Silver Lake. ♦