Chappell Roan had some blunt advice for Olivia Rodrigo after hearing about her disappointing experiences with men. The singer told her friend she needed to start dating women while the pair were working together in the studio, Rodrigo recalled in a new interview.
The 23-year-old singer shared the exchange while speaking with Zane Lowe for Apple Music alongside Roan, 28, as they discussed their new collaboration on Rodrigo's song 'expectations.' Rodrigo recalled how Roan reacted as she opened up about the 'crazy stuff' men had done to her while they were trying to write the track's second verse.
Chappell Roan Told Olivia Rodrigo To Date Women
'I have, like, a vivid memory of being in the studio with you, Chappell, and, like, we're trying to write the second verse,' Rodrigo recalled. 'And I was just, like, telling you all of, like, the crazy stuff that boys have done to me.'
Roan's response was immediate, according to Rodrigo, who remembered the singer saying, 'Oh my God, you need to start dating girls. This is crazy!' The anecdote offered a glimpse into the pair's friendship and the candid conversations behind their music.
The exchange also shed light on the new version of 'expectations,' which explores romantic disappointment from both singers' perspectives. Rodrigo's original lyrics centre on refusing to settle for less in a relationship, while Roan adds a new verse about taking a woman to a concert, only to be left waiting for a promised phone call.
Olivia Rodrigo and Chappell Roan Team Up on 'expectations'
The remix was released on 15 October, marking Roan's first official featured appearance on a Rodrigo song. The original track appears on Rodrigo's third studio album, you seem pretty sad for a girl so in love, released in June 2026.
Roan brings her own take on dating frustration, singing about taking a woman to a concert before being left without a promised phone call. 'She said she'd call me later / That was three weeks ago,' she sings, capturing the disappointment of being ghosted.
The updated track also arrived with a music video directed by Bardia Zeinali, which sees the two singers competing in a series of retro television game shows. Talking Heads frontman David Byrne appears as the host, while producer Dan Nigro, who has worked with both artists, also makes an appearance.
The Pair Have a Friendship Beyond Music
Rodrigo and Roan's collaboration builds on a connection that began before their first official musical feature. Roan previously opened for Rodrigo during her Sour and GUTS tours, performing for audiences who had come to see Rodrigo.
Olivia Rodrigo, Chappell Roan - ‘HOT TO GO!’ live from The GUTS World Tour on Netflix. pic.twitter.com/w1lnu2nn8E
— olivia rodrigo vocals (@oliviabestvocal) February 9, 2025
The two artists also appeared together at Rodrigo's Daisy Chain Fields festival in California on 29 August 2026. The women-led event raised $20 million (£15.1 million) for 10 non-profit organisations supporting women and girls, according to Universal Music Canada.
Their new collaboration brings that friendship into the music itself, with Roan adding her perspective to a song about romantic disappointment. The result gives both singers room to explore the frustrations of dating while maintaining the track's central message about expecting more from relationships.
