Olivia Rodrigo is pretty sad

Olivia Rodrigo is a funny little pop star in the grand scheme of things. A real throwback of how culture used to work before social media bolstered dead careers and killed lives ones before they were done. Seventeen, fresh out of Disney+ jail, and right into superstardom with her first single. It felt unfathomable at the time. Driver’s License (2020) is the type of generational hit that few performers get to unleash onto the world. Not just very good, and not just very successful, but the type of career defining track that can be both a gift and a curse.

Pop radio is still dealing with the fall out of Rodrigo’s first album SOUR (2021) and the shift in what everyone expected from our rising talent. Coming fresh of the heels of Billie Eilish and her ascent as the “weird” pop star of the period, this was something different. There was a wave of critical acclaim that anointed her as the face of what pop music could be. A return to tradition that swept away half a decade of insecurity by labels about new artist. We got dozens of well funded imitators flooding the market with angsty pop rock songs. The sound of the decade, packaged in one teenaged girl.

It did not last. Pop rock in that vein never caught on like record executives wanted it to. Like the Eilish wannabes of the preview few years prior (hi Tate McRae), those attempting to be Rodrigo either pivoted or died. The one star to ride on her coattails was personally selected by the pop star herself in the form of Chappell Roan, who also made a splash.

In many ways, it feels like Rodrigo figuratively peaked in high school. A teen star who will never be as big as her first song. That’s a cruel assessment, but SOUR was the type of big that you rarely get to do twice. GUTS (2023) was a very good follow up, but most of the singles underperformed by the standards of the previous album and it quickly became clear that she was no longer the shiny new toy. Now, in 2026, she’s dropped the third studio record, you seem pretty sad for a girl so in love. How does this one play out?

It is pretty sad.

This is a breakup record that did not begin as one. That isn’t to say that I will be providing meta context, because the record both deserves more than that and the gossip is uninteresting. But what you get from the album is an extended narrative of love curdling. It’s emotionally tense, full of insecurity and deep resentment about this man (who may or may not be multiple men) who has become the focus for everything inside of her that she is struggling to process.

The first half of the record is the “love” portion, and that descriptor should be taken with a grain of salt. For the girl who is in love is vulnerable and needy. The peak is honeybee, which is a quiet and vaguely desperate declaration of love. It does not escape my notice that this is the way Rodrigo has traditionally, aesthetically framed insecurity on other records - it almost reminds me of lacy from GUTS. That acoustic nervousness plays at at the edges of these early tracks. Rodrigo has always written about her emotions with an often theatrical sincerity, but third single stupid song is where the souring of the romance begins. Lead single drop dead was mostly playful, but stupid song is where that same framing goes from fun to worrisome. On their own, lines like “And if there is a God/He’s the bond that’s between us two” are beautiful in isolation. They’re also very intense and, in context the rest of the record, the beginnings of Rodrigo’s narration of codependence. She’s depressed for reasons she cannot yet explain and yet in love, which that is the only think that is good in her life.

The honeymoon period concludes with u + me = <3, where the romance fractures into a teenaged love affair. Which is not to say the song sounds juvenile. Instead, it utilises nostalgia as a weapon. This is a purposeful use of childish imagery to heighten how purely she has given herself to the relationship, singing of wanting to freeze this moment and that it is healing to be loved in this way. The song is the closest the record gets to a love song that isn’t choked by the looming end of it all, and that itself is a delusion. Hope does not spring eternal here. It’s a final moment of radical optimism before the record collapses into something more honest, and self-destructive, and visceral.

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my way is the best song on the record. Frenetic and anxious, Rodrigo directs her rage at the ex girlfriend who has the gall to still exist on the same planet as her. Who may or may not be provoking her online. Her simmering unease and those intense feelings of ownership bubble up and consume her. It’s a jealous and nasty little moment of pettiness where she’s gloating at a party that may not even be aware of her at all. It ends the first half of the record with something akin to a car crash, as the anxiety that has underpinned Rodrigo’s declarations of devotion overwhelm her. Whatever fiction of easy love she was living under is torn apart by this one manic moment. It will come back to haunt her.

Everything from this point forward is a slow admittance to herself that whatever this relationship is, it isn’t working. She claws herself away from the normalcy of her relationship with purple, which almost sounds like a love song until you take in the lyrics. Single the cure has her try to shift the blame inwards, while what’s wrong with me gives her the opportunity to vocalise that there is a problem with the relationship. begged has her admit that she hates having to ask for good things to happen. Then less happens.

less is the song where the break up happens and Rodrigo loses her ability to play in the weeds of this relationship anymore. It ends the farce that this is their problem to fix. “He” exits. Her honesty about her unhappiness has cost her the relationship. Those overwhelming feelings have subsided and now all they have, all she has, is the reality that affection is not enough. Or at least, that is is done trying to be the one to fix it. He cannot stick around as she keeps crying and begging him to love her the way he wants. In the context of the record, it feels like a punishment for opening up. For not being well and needing help.

The album ends with the one/two punch of expectations and cigarette smoke. The former is a sassy, bitter, funny moment of catharsis where Rodrigo lets loose on all she allowed in her relationship. She’s now got “expectations” of alertness and emotional awareness. But that bravado quickly falls back into something aching and upset as she lays into her ex partner on cigarette smoke. He has tainted her memories of him by his cowardice and decision to cut ties with her when things got hard. She would still be with him had he let her. Even if she deserves better, she’s lonely and lost all that time. The line “I resent you for taking her side” clarifies her anger in my way. The album closes with no real closure, because it all just hurts.

All of this takes place over fifty minutes, which is the album’s greatest flaw. There is an indulgence to the record that does come close to dragging, and I would argue that u + me = <3 and what’s wrong with me both could be dropped narratively without losing much. They’re both excellent songs, but even losing one of these tracks would help.

you seem pretty sad for a girl so in love sounds great. A marked improvement on SOUR and GUTS, which often felt overdone on the ballads. You can tell that she’s grown up a lot since the last record and that maturity shines through the record. Rodrigo has made no secret of her love for 1980s and 1990s rock music, and that shows up in the production of Daniel Nigro throughout. She still writes more like a pop artist than a rock star and sometimes that doesn’t work - the cure in particular has a chorus that doesn’t quite click for me - but it is more often a feature than a quirk. She is a pop star making pop rock for the masses. Hooks are not antithetical to rock music and there’s plenty of great ones here.

Rodrigo has also improved vocally. It’s less obvious than the overall production, but even the less vocally demanding moments on the record are clearer and less bogged by affects that are byproducts of being a very young person making music. GUTS had more than one track where Rodrigo was essentially forcing her voice to do things it sounded bad doing, like the slight accent present on ballad of a homeschooled girl or the clipped and strange way she sung the verses on the grudge. In context of that record these moments felt like nitpicks, but they’re completely absent on you seem pretty sad for a girl so in love and it makes a huge difference as a listener. She has a lovely voice and emotes well. The rest was unnecessary and she clearly agrees.

I don’t blame her for feeling the need to overcompensate at the time. As a stated earlier in the review, this is the girl with a million expectations on her. People would eat her alive if she just continued to make the same album over and over again. Pop stars already are not allowed to repeat or reflect. Everything must be reinvented within a limited scope of acceptable sounds and subjects. It is a prison I hope she knows only exists so long as she holds onto pop stardom. Using a break up album to expand her sonic world and prepare her audience for the future is a smart move.

you seem pretty sad for a girl so in love is, for my money, the best record that Olivia Rodrigo has released thus far. It’s sophisticated and complex without sacrificing her charms as a pop star. Is it a trifle long for what it is? Yes. But the songs on it are excellent and that maturity on display excites me for the future.