Inside Olivia Rodrigo and her ex-boyfriend, Joshua Bassett's dating timeline. What went wrong in their relationship? Find out.
Olivia Rodrigo is hogging the limelight for her professional front. For the unversed, on April 2, Olivia announced her highly anticipated third studio album, You Seem Pretty Sad For a Girl So in Love. The album is scheduled for release on June 12, 2026. The upcoming album is a follow-up to her sophomore album, Guts. Apart from her professional front, Olivia has always garnered the spotlight for her personal life.
Over the years, Olivia has had a fair share of relationships. Her most recent relationship was with actor, Louis Partridge. Reportedly, Olivia broke up with Louis, after two years of their relationship. But do you know, Olivia’s hit single, Drivers License is allegedly about her and Joshua Bassett’s breakup? Yes, you read it right. Many fans of Olivia thought that the hit single was all about her and Joshua’s breakup and his new connection with Sabrina Carpenter. If you are interested in knowing what led to Olivia and Joshua Bassett’s split, we’ve got you covered.
Olivia and Joshua first crossed paths during the filming of the TV series, High School Musical: The Musical: The Series. According to the report by Tuko, back then, Olivia was 16, and Joshua was 18. In the TV series, Olivia and Joshua played 'Nini' and 'Ricky', who were high school sweethearts.
Before finding love in Joshua Bassett, Olivia Rodrigo dated Ethan Wacker. For the uninitiated, Olivia worked with actor, Ethan Wacker on their show, Bizaardvark. Initially, they were good friends. Eventually, the close friendship blossomed into love and in 2019, the couple shared on a now-deleted Instagram post that they had been dating for six months. Reportedly, in 2019, Ethan and Olivia had split and remained friends.
In the same year, Olivia and Joshua came close while filming the TV series, High School Musical: The Musical: The Series. In August 2019, Olivia and Joshua grabbed a lot of attention with their performance at the Disney+ Showcase at Disney's D23 Expo in Anaheim, California. Joshua played guitar during the performance. The duo came together again in October 2019 and performed a duet during the 5th annual Elsie Fest: Broadway’s Outdoor Music Festival in New York City's Central Park. They dated from 2019 to 2020.
Showrunner, Tim Federle approached both Olivia and Joshua with the opportunity to write an original song for the series. According to a report by the Los Angeles Times, the duo exchanged voice memos to develop three different songs. Of the three options, the makers chose Just For a Moment. During the first season, Olivia and Joshua performed the song as a duet, and later, at the beginning of 2020, the song was released.
The song was all about Olivia and Joshua’s characters, 'Nini' and 'Ricky's' love story. Speaking to the Los Angeles Times, Joshua opened up about his and Olivia’s collaboration and also revealed that he had improvised the moment when 'Ricky' told 'Nini', he loves her for the first time in the show. He also added more details from his and Rodrigo's real-life experiences during the scene. He was quoted as saying:
"I think we understood each other. It was really neat ... how well we really did work creatively together, despite having disputes here and there. 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. I had no idea it was coming. Every single time, I would change it to something else that was specific to Olivia and me, and getting her reaction out of it was the best thing in the world."
Reportedly, Olivia and Joshua split around mid 2020. In July 2020, Joshua Bassett was seen at a Black Lives Matter protest with Girl Meets World fame, Sabrina Carpenter, in Los Angeles. Next month, in August 2020, Olivia posted a TikTok video in which she was eating a muffin as her song, All I Want from the TV series, High School Musical: The Musical: The Series, plays in the background. However, it was the caption, "And that's on failed relationships," that sparked breakup rumours. In October 2020, Joshua and Sabrina seemingly confirmed their relationship by sporting Halloween costumes inspired by The Adventures of Sharkboy and Lavagirl.
In December 2020, during an interview on Chicks in the Office, Joshua called Olivia a 'homie'. This further fuelled the speculation that the duo had split. While fans were wondering what went wrong in the relationship between Olivia and Joshua, she released the hit song, Drivers License. The lines of the song can be read as, "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." The lyrics made fans believe that the song was all about the alleged love triangle among Olivia Rodrigo, Joshua Bassett and Sabrina Carpenter that led to the couple’s split.
What are your thoughts on Olivia Rodrigo and Joshua Bassett's breakup? Let us know.
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