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Olivia Rodrigo and Joshua Bassett first met at the 2018 Radio Disney Music Awards on June 22, 2018. They were posteriorly cast on Disney+ series "High School Musical: The Musical: The Series" and were officially introduced to each other in February 2019, when the series' production started in Salt Lake City, Utah. Back then, Olivia was in a relationship with her fellow "Bizaardvark" co-star, Ethan Wacker. It was around that time that Bassett wrote a song called "Anyone Else" about falling in love with a girl who's dating another guy.
Sometime later, it was reported that Olivia and Ethan were no longer together. After their split, it seemed that Olivia and Joshua have gotten closer to each other. Over the months, Olivia was seen jumping into Joshua's arms during a trip with "HSMTMTS" cast, they went to an Ariana Grande concert together and also at a trip to San Diego with Olivia's best friend, Madison Hu, and Madison's boyfriend. Although dating rumors were increasing, they denied those dating rumors claiming to be "best friends".
It was around May 2020 that fans started noticing that their interactions had decreased. A month later, in June, Joshua was spotted for the first time with singer and former Disney actress, Sabrina Carpenter. Joshua later released "Anyone Else" officially and it was speculated that Carpenter was filming him in the music video.
In January 2021, Olivia Rodrigo released her debut single called "Driver's License" and both fans and media outlets started speculating the song was about Bassett. In the lyrics, Olivia sings about a recent breakup and how her ex moved on with someone else quickly after their split, and how she doesn't understand how her ex could be "so okay" while she's still suffering from their separation. She hints at her ex for not meaning what he said in a song he wrote for her — which fans immediately associated to Joshua Bassett's "Anyone Else" as he wrote, "How am I supposed to think about anything else?/How am I to go on keeping this to myself?/I am done pretending I want anyone else".
She also hints at her ex for "probably" being in a relationship with a blonde girl who's much older than her. Sabrina Carpenter was immediately associated as "the blonde girl" that Rodrigo was talking about in her song, as she's four years older than Rodrigo, has blonde hair and was romantically linked to Bassett only a few months before "Driver's License" release. A week after "Driver's License", Carpenter released "Skin"—supposedly about the whole drama revolving around her relationship with Joshua and her so-called rivalry with Olivia Rodrigo. "Maybe we could've been friends/If I met you in another life [...] Maybe you didn't mean it/Maybe 'blonde' was the only rhyme" she sings, hinting at "that blonde girl" line from "Driver's License".
Several songs off Rodrigo's debut album "Sour" were rumoured to be referencing Bassett and his new relationship with Carpenter, including "Deja Vu"—in which Olivia calls her ex out for doing with his new girlfriend the same things he used to do with her, such as watching the same TV shows, singing the same songs and eating at the same places they used to go; "Good 4 U" where she once again calls Bassett out for moving on easily after their split, "Well, good for you/I guess you moved on really easily/You found a new girl, and it only took a couple weeks"; and "Traitor" in which Olivia hints that Joshua and Sabrina were texting each other while he was still dating her, and although he maybe didn't cheat on her, he was "still a traitor".
Rodrigo, Bassett and Carpenter's "love triangle" turned into a media circus during the first half of 2021, which resulted in both Bassett and Carpenter receiving death threats online from Olivia's fanbase. Joshua even got hospitalized for getting "too much stressed" over the backlash, and almost died out of a heart failure.
In early December, Joshua released an EP with three songs, including "Crisis" a song that was reportedly written about Olivia. In the song, he calls her out for messing with his life "as a career move", claiming that he also got hurt from their breakup, and that he wasn't the "bad guy" at all.
In July 2022, Joshua and Olivia were pictured together in public for the first time since the whole love triangle drama, at the "HSMTMTS" Season 3 premiere. In September, he released a new EP called "Sad Songs in a Hotel Room" which includes "Used To It" a song that is also speculated to be about Olivia. "I'm not surprised you didn't call/When I almost died you didn't care at all" he sings.
In October 2022, Bassett released songs "Would You Love Me Now?" and "I'm Sorry" that are rumoured to be about Olivia. In these songs, he talks about regretting hurting an ex-lover (rumoured to be Rodrigo) and claims he wishes he could talk to his ex once again just to say he's sorry.
EDITED ON DECEMBER 4, 2022
NOTES: As of November 2022, a few people on TikTok started theorizing that Olivia Rodrigo and Joshua Bassett are dating again, due to his recent songs' lyrics. However, there's not a slightest proof of that, as they were NOT seen or photographed together. This page will be updated to "Dating" if there's a confirmation or something a little bit more suspicious than just a few song lyrics suggesting anything. Until that, they're NOT in a relationship again.