Joshua Bassett Is Down Bad for Olivia Rodrigo

His weekly single drops are positively pining for her.

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Joshua Bassett Is Down Bad for Olivia Rodrigo
Photo:David Livingston (Getty Images)

Olivia Rodrigo and Joshua Bassett shocked the world on the High School Musical: The Musical: The Series red carpet this past summer by giggling together after the most dramatic breakup in Gen Z history. The monumental reconciliation was enough for many to put the Olivia-Josh-Sabrina love triangle (no, I will not explain this to you) to bed. I, however, suspected that the teenybopper never-actually-confirmed relationship and breakup that inspired the heart-wrenching, record-breaking ballad “drivers license” (and the entirety of Rodrigo’s debut album SOUR) wouldn’t wrap up so cleanly.

And now, it would appear (according to my close readings) that the 21-year-old Bassett is all but begging for Rodrigo back. Suspicions among fans with laser focused analyses have been percolating for weeks since Bassett first dropped “would you love me now?” (hello!! title!!) on Oct. 6, and after yesterday’s release of “Different,” I have to break my silence and join the chorus of hopefuls. Over the past few weeks, Bassett has also released two other singles titled “SHE SAID HE SAID SHE SAID” and “i’m sorry.” Barring that all-caps song (which I think hints a bit at his lingering spite about how things went down), Bassett is on his musical hands and knees and crawling back as fast as his guitar strings can carry him.

Allow me to walk you through some of the most revealing lines of these songs. On “would you love me now?” he asks: “If I showed up at your doorstep / Would you turn me away? / Would you care to see a stranger whose eyes are still the same? […] And I’ve still got the Converse that I wore the day we met / I’m running out of reasons to do it all again.”

On “i’m sorry,” he sings: “I thought about what I would say / But I’m two years too late / I can’t imagine how you’re doing these days / Sure it wasn’t perfect back then / I’ll be first to admit / But it’s better than being strangers again.”

And then “Different” really seals the deal: “Darling how I missed you / Two years not even friends / And I’m trying not to kiss you / Cuz we’ve seen how this can end / […] I’m back in your arms / But it’s not the same / Yeah we’ve been through hell and back again.”

At the risk of sounding like a YouTube conspiracy theorist (or a Swiftie), Bassett’s repeated mention of a relationship that happened two years ago and the growing distance between two former lovers all point straight to Ms. Rodrigo. The HSMTMTS star told GQ in December 2021 that he hadn’t spoken to her since “drivers license” first came out in January of that year (and not for lack of reaching out, apparently). It seems, then, like all he’s been left to do since is pine.

Bassett has put out quite a bit of music since he and Rodrigo called it quits in late 2020, but this most recent batch of songs contains more direct references to feelings of regret than anything he’s released before. Tracks off his 2021 EP— like “Crisis” and “Set Me Free”—convinced me that the door of Joshlivia was indeed slammed shut, never to be cracked open again. And yet, with “Different” and the other recent tracks, it seems like reconciliation could be on the horizon.

Two years out, Bassett’s been a pretty good sport about the romantic turmoil that once made him the target of hostile pro-Olivia online hate, playfully waiting for a different letter to appear when a TikTok filter recently told him that the name of the love of his life started with the letter O (the algorithms don’t lie!!). As for Rodrigo, she’s been in a few relationships since being linked to Bassett, but reportedly broke things off with her latest beau, Zack Bia, in August.

With as far as Joshua’s sticking his neck out, I wouldn’t be mad if Olivia just went ahead and leaned in for a kiss already. I guess we’ll only know for sure once her sophomore album comes out.

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