Enough, songwriters. The oldest known love song is 4,000 years old (inscribed on a Sumerian cuneiform tablet in Nippur, Iraq). And here you all are, still working out new ways to express the feeling.
Enough with cathartic break-up anthems too. We’ve learnt to Believe in life after love (after love, after love); emerge Happier Than Ever; and say Thank U, Next.
But songs about regret? The bitterness that has nowhere to go, and keeps pricking at the psyche, poking holes in our sense of self? There are always interesting new paths to take there.
Check Spotify. Most prompts lead into heartbreak territory: classic shoulda-woulda-couldas. Johnny Cash (or Nine Inch Nails). Janis Joplin looking to “trade all of my tomorrows for one single yesterday”. There is much of SZA’s SOS. About half of Taylor Swift’s discography, and 60% of all Country music.
Lately, the songs have been getting oddly specific too, especially the ones sung by women. Consider Doodles, by Irish singer Rose Betts. She went viral in 2022 for saying the best part of going on a date was Driving Myself Home. Doodles, released in 2025, honours every misstep (“the doodles I’d undo”) with a drink. “One for the joke that I took too far / One for the dent in the rental car”. It turns remorse into a happy drinking song, which might be better than wallowing in guilt.
There’s a bit of meta-regret in Regret Me, from the 2023 series Daisy Jones & The Six, based on the 2019 novel of the same name. The track was meant to be something penned quickly, after the lead singers from the story’s fictitious ’70s band almost kiss during a songwriting session. But author Taylor Jenkins Reid’s lyrics from the book are tweaked for the screen.
The track retains some fire: “You couldn’t handle your liquor / And you can’t seem to handle the truth”. But it does away with the best line: “And, baby, when you think of me / I hope it ruins rock ‘n’ roll.”
The stage musical Hamilton came out in 2015. I’m including it here because it broke into the mainstream with the pandemic-era telecast in 2020. It contains the queen of modern regret songs: Satisfied. This isn’t just about the one that got away. It’s about the one you saw, liked and flirted with, who liked you back, but whom you introduced to your smitten sister, who ended up marrying him. Renée Elise Goldsberry sings, raps, and all but breaks down on this track, playing Angelica Schuyler.
Even Chappell Roan — the voice on Hot to Go and Pink Pony Club — has twisted the regret track into something that fits the way definitions of love blur today. In Casual (2023), she leans into the bitterness as she tries to understand a situationship: “It’s hard being casual / When my favourite bra lives in your dresser / And it’s hard being casual / When I’m on the phone talking down your sister.” She finds a way out of her confusion. “I hate that I let this drag on so long, now I hate myself / Hate that I let this drag on so long, you can go to hell.” A bonus: The video in which Roan kisses her self-loathing alter ego back from brink only to witness a crushing twist at the end.
On I Love You, I’m Sorry (2024), Gracie Abrams’s regret goes deeper, displaying surprising self-awareness. You could hear it just as a woman thinking back on a relationship that ended “two Augusts ago” when she admitted her feelings and he split (she’s singing into an A***ole of the Year trophy in the video). But play it over and it seems more like she’s acknowledging her flaws: “I like to slam doors closed”, “I push my luck, it shows,” “I stare at the crash, it actually works,” “Trust me, I know it’s always about me”. That A***ole trophy is her own. And the regret is not the breakup, but that she can’t seem to break her own curse. It’s more devastating, somehow.
Listen to the full regrets playlist here.
