Olivia Rodrigo is at her complicated best on her heartbreaking new album

Annabel Ross

June 13, 2026 — 5:30am

Olivia Rodrigo chronicles her first “big girl relationship” on You Seem Pretty Sad for a Girl So in Love. Olivia Rodrigo, You Seem Pretty Sad for a Girl So in Love

★★★★

Olivia Rodrigo’s origin story is familiar: child Disney star pivots effortlessly to pop, with the modern addendum of a TikTok hit helping her ricochet to the top of the charts. Three albums in, Rodrigo is the only star in history to top the Billboard charts with three consecutive lead singles, an outrageous accomplishment for a 23-year-old.

It’s a testament to the uniform quality of her work so far – evergreen love/friendship/identity angst made compelling through Swiftian lyrical specificity, influence-checking, superbly crafted pop and a rebellious streak that comes with a fascinating set of contradictions.

Her dark horse qualities are recognisable to mature fans who relate, but well-disguised enough to sail over the heads of her tween admirers. When some try to describe her pop as punky, they’re met with sneers from those who view Rodrigo as a manufactured star, a product of the machine. But as one of the highest profile entertainers in the world to speak out on everything from reproductive rights to Gaza, Rodrigo is nobody’s puppet.

On albums one and two, Rodrigo pined and seethed with equal intensity. Her heady crushes were all-encompassing, but on tracks such as Traitor , All-American Bitch and Vampire , she was out for blood. If Sour and Guts spelled out a mood with a single word, You Seem Pretty Sad for a Girl So in Love reflects a more complicated emotional landscape.

The 23-year-old singer is less rageful and more wistful on her new album. The story of her first “big girl relationship”, its bright beginnings and unravelling, were chronicled in real time. Set to melodies less rageful and more wistful, the songs were rendered “a little more honest and sad and creepy” with the help of longtime producer Dan Nigro, a favourite among stormy chanteuses from Sky Ferreira to Caroline Polachek and Chappell Roan.

Early in her career, Rodrigo was effusive in her admiration of Taylor Swift, who likewise championed the younger singer – until Rodrigo’s frankness about her inspirations saw Swift, Jack Antonoff and Annie Clark added to songwriting credits (and future royalty cheques) on Sour . By all accounts, Rodrigo and Swift have not been on friendly terms since. The experience clearly wounded Rodrigo but has made her more, not less, forthcoming about what’s in her musical DNA.

In a series of respectful, mutually admiring appearances, she’s shared stages with idols including Jack White, David Byrne, and at last year’s Glastonbury, The Cure’s Robert Smith. On You Seem Pretty Sad for a Girl So in Love , she name-checks Just Like Heaven in the dreamy Drop Dead , describing the dizzying experience of a crush finally realised – at the bar.

The spooky bass line that kicks off Maggots for Brains owes a clear debt to The Cure’s A Forest , but the lyrics are considerably weaker, barring the wincingly honest, “I’m a sad shell of a woman and I’ve got maggots for brains/But that’s just a thing that happens when my baby goes away.”

If What’s Wrong with Me seems a fittingly titled track for emo icon Smith to appear on, his vocal turn is a charming surprise. Harmonising with Rodrigo on the countrified chorus, his verse inverts decades of yearning to reach a new, equally miserable conclusion: “What if this isn’t what I want?”

Rodrigo’s lyrics are intriguing; sometimes banal, but often their mundanity serves a standout line that echoes hours – or days – later, or is elevated by a searing delivery and arrangements nimble and wily enough to bestow profundity or wonder. A low, dirty bass line wriggles into the final third of Stupid Song like a delicious rumour; on Expectations , where Rodrigo asserts new standards following her relationship’s demise, whirling synths foreshadow a chorus of masculine robots in the bridge evoking the deadpan whimsy of Devo.

There’s no hiding Rodrigo’s magpie tendencies. On Drop Dead , it’s a spoken word starry-eyed fantasy sequence modelled after Wolf Alice’s Don’t Delete the Kisses . Alanis Morissette’s spare, tortured vocal in Your House (the hidden track on Jagged Little Pill ) might have inspired Rodrigo’s delivery in Begged , while The Smashing Pumpkins’ Disarm can be heard in the opening chords of The Cure . It’s a spellbinding song and the album’s most devastating, a realisation that not even love will quell her jealousy of “all the pretty girls in the foreground of my mind”.

Rodrigo says the track is not an ode to Smith’s band, but it’s kind of nice to think otherwise. Its defining line functions as a double entendre befitting one of pop’s biggest fangirls: “It doesn’t matter how your love feels any more/it will never be the cure,” she sings. Romance might fade, but perfect pop songs are eternal.

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