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Rodrigo's musical career has skyrocketed. The singer took home seven Grammys in 2022, including best new artist and album, for her debut Sour. The album features tracks largely thought to be inspired by her relationship with Bassett.
While the musicians have never officially confirmed their romance or split, fans haven't stopped trying to piece together what happened between them — or how fellow Disney star Sabrina Carpenter fits into the equation.
Here's everything to know about the young stars' former romance, from playing on-screen love interests to where they stand now.
February 2019: Olivia Rodrigo and Joshua Bassett first meet on the set of High School Musical: The Musical: The Series
In early 2019, the cast and production were announced for the Disney+ spinoff of the High School Musical franchise, which follows a group of high school students putting on a musical production of HSM. Rodrigo, then 16, and Bassett, then 18, first met while starring as on-screen love interests Nini and Ricky, who land the roles of Gabriella and Troy in HSM.
August 23, 2019: Olivia Rodrigo and Joshua Bassett perform together
The actors took the stage together in summer 2019 for a sneak peek of their musical compatibility. Bassett played guitar during their performance at the Disney+ Showcase at Disney's D23 Expo in Anaheim, California.
October 5, 2019: Olivia Rodrigo and Joshua Bassett perform together in New York City
November 5, 2019: Olivia Rodrigo and Joshua Bassett appear on PEOPLE Now
The HSMTMTS cast stopped by PEOPLE Now ahead of the series premiere to share their favorite songs from the original HSM films. Rodrigo and Bassett sat next to each other during the interview.
November 8, 2019: High School Musical: The Musical: The Series premieres starring Olivia Rodrigo and Joshua Bassett
The series premiered in early November, nine months after Rodrigo and Bassett first met. Their on-screen chemistry as Nini and Ricky seemed to bleed into real life, with fans immediately interpreting the actors' frequent Instagram selfies together as proof of a real-life romance.
January 2020: Olivia Rodrigo and Joshua Bassett discuss writing their song together
Showrunner Tim Federle approached the duo with the opportunity to write an original song for the series, so Rodrigo and Bassett got to work collaborating on a piece that spoke to their characters' love story. According to the Los Angeles Times, the pair exchanged voice memos to develop three different song options before ultimately deciding on "Just For a Moment." They performed the song as a duet during the first season, and the track was released at the beginning of 2020.
"I think we understood each other. It was really neat ... how well we really did work creatively together," Bassett told the L.A. Times, despite having "disputes here and there."
Bassett also revealed that he improvised the moment when Ricky tells Nini he loves her for the first time in the show.
"It is the most powerful feeling in the world when you don't even have to think, and it just comes through you. It was really a magical moment," he said, adding that Rodrigo "had no idea it was coming."
He also shared that he added more details from his and Rodrigo's real life experiences during the scene, charging the moment with his specificity. "Every single time, I would change it to something else that was specific to her and I, and getting her reaction out of it was the best thing in the world," Bassett told the outlet.
Rodrigo told the L.A. Times that working alongside Bassett felt natural. She recalled one of the instances in which he improvised to her while filming, and admitted that the poignancy of it made her tear up.
"He said, 'Remember that one time that we wrote a song, and we didn't know if anybody would like it?' That one made me cry because I just remembered sharing those memories with him," she said of the actor. In one of her only public statements directly regarding him, she added, "I love him so much. He's my best friend … It was like I wasn't acting."
July 2020: Joshua Bassett is spotted out with Sabrina Carpenter
In July 2020, Bassett was seen at a Black Lives Matter protest with Girl Meets World star Sabrina Carpenter in L.A., prompting speculation that he and Rodrigo had split.
August 2020: Olivia Rodrigo posts about "failed relationships" amid speculation of split from Joshua Bassett
Soon after Bassett and Carpenter were seen together, Rodrigo posted a TikTok video that seemed to imply that a relationship had ended. The clip sees her eating a muffin as her song "All I Want" from HSMTMTS plays in the background. In the song Rodrigo sings, "All I want is a good guy / Are my expectations far too high? / … All I want is love that lasts / Is all I want too much to ask?"
She captioned the clip, "And that's on failed relationships."
October 2020: Joshua Bassett and Sabrina Carpenter coordinate Halloween costumes
The Disney stars seemed to confirm their romance by showing off their Halloween costumes inspired by Adventures of Sharkboy and Lavagirl. One TikTok video included the pair playfully reenacting the 2005 movie.
December 2020: Joshua Bassett calls Olivia Rodrigo "really wonderful"
The actor opened up about his relationship with Rodrigo during an interview on Chicks in the Office, recalling how they spent "every hour on and off set" writing "Just For a Moment" together.
"We definitely spent a lot of time together, and she's really wonderful," he said of their "very close" friendship. "She's a homie for sure."
His referring to Rodrigo as a "homie" further fueled fan speculation that the pair had split.
January 8, 2021: Olivia Rodrigo releases "drivers license," seemingly about her split from Joshua Bassett
Olivia Rodrigo Instagram
On the record-breaking track, Rodrigo addresses a love interest, singing, "And you're probably with that blonde girl / Who always made me doubt / She's so much older than me / She's everything I'm insecure about."
Fans quickly interpreted the song to be about the alleged love triangle between Rodrigo, Bassett and Carpenter, who is blonde and nearly four years older than Rodrigo.
January 2021: Joshua Bassett shows support for Olivia Rodrigo's new music
There didn't appear to be any bad blood between the supposed exes at the time of the song's release, however. Bassett promoted "drivers license" on his Instagram story and called it "such a great song."
January 2021: Olivia Rodrigo addresses the speculation around "drivers license" and Joshua Bassett
Speaking to Billboard, the singer opened up about the rumors surrounding her hit single.
"I totally understand people's curiosity with the specifics of who the song's about and what it's about, but to me, that's really the least important part of the song," she told the outlet. "It's resonating with people because of how emotional it is, and I think everything else is not important."
January 14, 2021: Joshua Bassett releases a new song
Soon after "drivers license" dropped, Bassett released "Lie Lie Lie." Fans immediately took it as a response to Rodrigo's breakup ballad, although Bassett had been teasing his single on Instagram since 2019.
In the song, Bassett sings, "I know what you say about me / I hope that it makes you happy / You can't seem to get me off your mind."
February 1, 2021: Joshua Bassett supports Sabrina Carpenter's song addressing Olivia Rodrigo drama
ANGELA WEISS/AFP/Getty; Gregg DeGuire/FilmMagic; JC Olivera/WireImage From L to R: Sabrina Carpenter, Olivia Rodrigo and Joshua Bassett
In February 2021, Carpenter released "Skin," appearing to address the drama between herself and Rodrigo.
The lyrics "Maybe you didn't mean it / Maybe blonde was the only rhyme," caught fans' attention, as well as what appeared to be a direct reference to Rodrigo when she sang, "Don't drive yourself insane."
Bassett showed support for Carpenter's single on Instagram. "Been stuck in my head since I heard it," he wrote alongside the "Skin" single cover. "Congratulations @sabrinacarpenter on 'Skin', the new label & all that's to come!!!"
Bassett and Carpenter also collaborated on "We Both Know" around this time, but opted to delay the release as Bassett didn't want the ongoing drama to overshadow the music. "You shouldn't live to please everybody, but at the same time, there are ways to be sensitive to situations where maybe [the duet] has a better chance at a different time," he told Billboard.
February 21, 2021: Joshua Bassett responds to Saturday Night Live's sketch about Olivia Rodrigo's song
The singer responded to a Saturday Night Live sketch about the popularity of Rodrigo's "drivers license," posting a TikTok video of himself enthusiastically opening up his laptop after a "friend" told him that he was "on SNL last night."
The actor then catches a moment in the sketch where Mikey Day's character says he loves Rodrigo's song because his "bitch ex Gina is Joshua Bassett."
In response, Bassett shuts his laptop and stares blankly at the camera, with Kacey Musgraves' song "Happy & Sad" playing in the background.
"Dream come true?" Bassett captioned the clip.
March 2021: Olivia Rodrigo addresses love triangle rumors with Joshua Bassett and Sabrina Carpenter
Walt Disney Company/Image Group LA via Getty
Rodrigo addressed the rumors that she and Carpenter were at odds, telling Radio.com that they had hardly ever interacted.
"I actually don't know her at all," Rodrigo said. "I think we've met once or twice in passing, but I've never had a conversation with her."
She then shut down speculation that she would write a reply track to Carpenter's "Skin," explaining, "I don't think I could write a song that was meaningful or emotional about somebody that I don't know."
May 11, 2021: Joshua Bassett comes out as part of the LGBTQ community
The "Only a Matter of Time" singer hinted at his sexuality in an interview during which he described Harry Styles as "hot," later saying it was his "coming-out video."
He later addressed the interview on Instagram, writing, "My entire life people have told me my sexuality. People have shamed me for things they know nothing about. I want to say thank you to those of you who stand for love and acceptance." He continued, "Love who you love shamelessly. It's ok to still be figuring out who you are. Life's too short to let ignorance and hatred win. I choose love. ❤️🧡💛💚💙💜"
The following month, Bassett confirmed in an interview with GQ that he "wasn't joking" about being part of the LGBTQ+ community. "I stood behind every word that I said," he said.
December 3, 2021: Joshua Bassett releases three breakup tracks, which seemingly address Olivia Rodrigo
In December 2021, the singer dropped three emotional ballads that fans took to be inspired by Rodrigo: "Crisis," "Secret" and "Set Me Free." Deep dives into the lyrics reveal lines that seem to hint at their relationship. On "Crisis," Bassett sings, "If you get to tell your truth / Then so do I / And it's cool if you want me to play the bad guy / But don't you dare act like I didn't love you."
December 2021: Joshua Bassett says he and Olivia Rodrigo haven't spoken in nearly a year
In December, the "Feel Something" singer told GQ that he and Rodrigo hadn't spoken for the duration of 2021.
"[Rodrigo] hasn't spoken to me since 'drivers license' came out," Bassett said, noting that he had reached out to her.
March 23, 2022: Joshua Bassett says he isn't looking to date right now
Ryan Pfluger Joshua Bassett
The Better Nate Than Ever star opened up to PEOPLE about his current mental state, noting that he isn't looking for love at the moment. Bassett came out as part of the LGBTQ community in 2021, and told PEOPLE that he feels "much more liberated" after doing so.
"Dating is not on my radar," he said. "I'm working on myself so much, and the place I'm in right now, I really only have energy for myself."
May 22, 2022: Olivia Rodrigo is confirmed as a guest star on HSMTMTS season 3
While it's unclear if Rodrigo and Bassett will share the screen, the two Disney stars are both confirmed to return to the hit series for season 3, which premieres on July 27, 2022. Rodrigo will return as a recurring guest, while Bassett will return as a series regular. The Disney+ series was also greenlit for season 4.
July 27, 2022: Olivia Rodrigo and Joshua Bassett reunite on the red carpet