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Olivia Rodrigo and Joshua Bassett Relationship Timeline: from Co-Stars to Breakup

Olivia Rodrigo and Joshua Bassett
Olivia and Joshua for the Red Carpet of High School Musical (Credits: Vulture)

Olivia Rodrigo has proved herself more than just a break-up artist with 3 Grammys, but fans are more than thankful for her sweet and ‘sour’ breakup lyrics about Joshua Bassett. They never officially confirmed their dating status. They went private, and their relationship wasn’t public.

In ‘Sour,‘ Rodrigo expresses her heartbreak for Joshua, but her ex has been going through his heartbreak. He was tormented by hate and death threats, and he felt his heart failing. He was diagnosed with a heart attack, and the doctors said that he would have died in his apartment if he hadn’t checked in before.

Who are Olivia Rodrigo and Joshua Bassett?

Bassett is Disney’s Prince Charming, who won the 2022 Kid’s Choice Awards. The American actor is best known for his role as Rick Bowen in High School Musical: The Series since 2019. He has worked on over thirty music productions.

Olivia Rodrigo signed with Interscope Records, and her debut single, driver’s License, was chart-topping, record-breaking, and best-selling in 2021. Her solo album Sour won three Grammys for a single album. The Billboard Woman of The Year has created hits ‘Deja Vu’ and ‘Good 4 U‘.

Olivia Rodrigo and Joshua Bassett Relationship Timeline: from Co-stars to Breakup

February 2019: On-screen and off-screen lovers Bassett and Rodrigo starred in High School Musical as Nini and Ricky. The sophomore dating and chemistry of the East High Teens are interpreted as real-life romance by fans.

August 23, 2019: Rodrigo and Bassett perform together on stage at the Disney+ D23 Expo showcase in Anaheim, California. Bassett played guitar, and fourth-season teasers were given.

October 5, 2019: The couple performs together in New York in the fifth annual Elsie Fest: Broadway’s Outdoor Music Festival. They sang the Breaking Free song from HSM musical series. Both Joshua and Olivia had fun with the extra loud crowd.

November 5, 2019: Rodrigo and Bassett attend a People Now interview. The entire cast discusses favorite songs from HSM films. Bassett sang Finally Free, Let You Go, I Think I Kinda You Know from the High School Musical 3 soundtrack.

November 8, 2019: Rodrigo and Bassett’s Instagram were interpreted as real chemistry. Fans get to see the Ricky and Nini romance for the first time.  Ricky and Nini eventually break up in High School Musical.

Ricky and nini HSM

High School Musical Still of Ricky and Nini (Credits: TV Guide)

January 2020: Bassett and Rodrigo are approached for songwriting for the series.  They exchange voice memos and create collaborations that fans love. Olivia has her first songwriting experience.

July 2020: Joshua was seen with Sabrina Carpenter, which sparked rumors that Rodrigo and Bassett had split. Fans think Sabrina and Joshua are together. Joshua talks about being told to slide into her DM’s.

August 2020: Rodrigo posts TikTok videos that look like signs of a breakup. She sings ‘All I Want’ from the HSM soundtrack and eats a muffin. She sings ‘All I want is a good guy, are my expectations too high?’ and fans think she was singing about Bassett’s split with her.

December 2020: Joshua calls Olivia a homie, working for hours on the song ‘Just for the Moment’ and a close friend. He describes spending a lot of time with her and says that she is wonderful.

January 8, 2021: Olivia Rodrigo released her ‘Driver’s License,’ which looked like she was talking about a failed relationship. The charted on Billboard Hot 100 at the no. 1 spot, and the lyrics about a blonde girl who is older than her point at Sabrina. The girl causes Olivia insecurities.

January 14, 2021: Bassett teases a new song ‘Lie Lie Lie‘ on Instagram which fans think is a response to Olivia’s breakup song. He promotes ‘Driver’s License’ on Instagram which seems to be about Joshua Bassett.

March 2021: Rodrigo talks about the drama that revolves around Carpenter’s song ‘Skin‘ and the drama of Olivia Rodrigo and Sabrina Carpenter’s love triangle. ‘I don’t know her at all. I don’t think I could write a song about somebody I don’t know. We’ve never had a conversation. ‘

Emotions After Breakup

Bassett has revealed trying to contact Olivia for a while, but they haven’t spoken for more than a year. Olivia reveals how she copes with a breakup: cutting all contact and forgiving both parties in the relationship.

‘People don’t know what they are talking about,’ he says. ‘It was like food poisoning,’ he said, referring to the death threats. ‘I’m happy to be part of the LGBTQ+ community because they embrace it all.’ Writing songs was painful for him, especially the ones speculated as breakup songs about Olivia.

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