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Fans Think Joshua Bassett Is 'Crashing Out' as Ex-Flames Olivia Rodrigo and Sabrina Carpenter Get Ready to Headline Lollapalooza
Olivia Rodrigo and Sabrina Carpenter will headline Lollapalooza. Fans are buzzing online, joking that their mutual ex, Joshua Bassett, might not be thrilled about the news.
Olivia Rodrigo and Sabrina Carpenter have been announced as headliners for this summer’s Lollapalooza music festival in Chicago. The event will take place from July 31 to August 3 and will feature a lineup of A-list artists, including Tyler, the Creator, A$AP Rocky, Doechii, and Luke Combs, as per Daily Mail.
The announcement has sparked excitement among fans, with some referencing the singers' alleged past connection through their mutual ex, Joshua Bassett.
After the Lollapalooza lineup was revealed, fans quickly took to social media to share their thoughts. Many pointed out that Rodrigo and Carpenter were previously linked to Joshua Bassett and speculated about his reaction.
One fan wrote on X (formerly Twitter), “Joshua Bassett is crashing out right now.” Another referenced the rumored past tension between Olivia and Sabrina over Bassett, writing, “In my head Olivia Rodrigo and Sabrina Carpenter are still beefing over Joshua Bassett.”
Both Olivia and Sabrina shared their excitement about the festival on social media. Sabrina posted on her Instagram Story, writing, “Awww sh*t,” while Olivia posted on Instagram, writing, “Wohoo!!!” with pink heart and flower emojis.
The announcement comes as Olivia continues her GUTS world tour, which began in February 2024 and runs through July 1, 2025. Meanwhile, Sabrina is currently on her Short N’ Sweet tour, recently performing in Birmingham, Glasgow, Manchester, and Paris.
Rodrigo and Bassett were rumored to have dated while filming High School Musical: The Musical: The Series, which premiered on Disney+ in 2019. Their reported breakup became a major topic among fans when Olivia released Driver’s License in January 2021, a song believed to be about Bassett.
Many fans also speculated that Carpenter was the 'blonde girl' mentioned in the lyrics. Olivia sang about someone who was much older and made her doubt the relationship. Sabrina, who is three years older than Olivia, was linked to Bassett in 2020, but they had broken up by 2021.
Currently, Olivia is dating actor Louis Partridge, while Sabrina was in a high-profile relationship with Barry Keoghan in 2024.
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