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Joshua Bassett Caught Up with Olivia Rodrigo in a Shiny Black Suit

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One perk of celebrity: getting to decide what to wear when you run into your ex.

Joshua Bassett Caught Up with Olivia Rodrigo in a Shiny Black Suit

David Livingston

You don’t typically get to decide what you’re wearing when you run into an ex. No matter where you live, there are only so many good grocery stores, or restaurants, or sidewalks. But if you are Olivia Rodrigo and Joshua Bassett—who started dating while playing on-screen love interests on Disney’s High School Musical: The Musical: The Series, broke up, and used that breakup to fuel some legitimately chart-topping music—your professional obligations may spare you the surprise encounter, at least publicly. Surely, the season premiere of the television show you’re both in is as good a time as any to get the funny-seeing-you-here look out of the way.

Rodrigo and Bassett both hit the red carpet to support HSMTMTS season 3 clad in all black, though that was likely more of a copacetic coincidence than a considered coordination. For his part, Bassett wore a cropped, peak-lapelled Saint Laurent black satin jacket and trousers, with a simple A-tank and black-painted nails to match; Rodrigo, in a sweet Nensi Dojaka set. They posed affably alongside each other, the effect of which probably earned a little boost from some unintentional sartorial harmony.

Certainly, it’s a tricky thing to date and become famous while portraying a couple on TV, especially if one or both of you become considerably more famous for breaking up in real life. Last summer, when Rodrigo’s album was burning up the charts, Bassett reflected on his HSMTMTS casting process, during which the show’s writers told him that his own success in the role would hinge on his chemistry with his yet-uncast love interest. During his final audition with Rodgrigo, he recalled to GQ, “it was very obvious, in my opinion, that she was the perfect one for it. … I think people can tell when they watch the show. It was just an instant sort of connection.” By the end of the year, Bassett admitted that “[Rodrigo] hasn’t spoken to me since ‘Drivers License’ came out.” But a lot can change in a year, even if it only goes so far as to what one can glean from the red carpet.

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