Olivia Rodrigo and Chappell Roan have plenty in common when it comes to making pop music, but apparently, their friendship also includes some hilariously candid conversations about dating.
During an October 15 appearance on Apple Music with Zane Lowe, Rodrigo revealed that Roan once offered an unexpected solution to her romantic frustrations: perhaps it was time to consider dating women instead.
The suggestion came during a recording session when Rodrigo was sharing stories about her experiences with men. As the two worked on the second verse of their collaboration, Roan was apparently so surprised by what she heard that she jokingly encouraged her fellow pop star to rethink her dating options.
The lighthearted revelation offered fans a glimpse into the friendship behind their musical partnership, which recently produced a remix of Rodrigo’s song “expectations.”
Released October 15 alongside a music video, the collaboration brings together two of pop music’s most recognizable young performers. The original track appears on Rodrigo’s latest studio album, *you seem pretty sad for a girl so in love*, which arrived in June 2026 and debuted at No. 1 on the Billboard 200.
Beyond their amusing studio conversations, Rodrigo explained that Roan played a significant role in shaping the spirit of the song.
Rather than creating another track centered primarily on describing her emotions, Rodrigo wanted to write something she could perform as a personal declaration of confidence. Roan’s unapologetic attitude and commanding presence became an important source of inspiration.
That influence eventually developed into a full-fledged collaboration, giving Roan an opportunity to contribute her own perspective to the recording.
For Roan, the project carried additional significance because it allowed her to incorporate queer themes into a mainstream pop release. She praised Rodrigo for welcoming that perspective and viewed the collaboration as an expression of female empowerment and artistic solidarity.
The remix also marks an important milestone in Roan’s recording career as her first featured appearance on another artist’s track. It follows her 2025 release “The Subway.”
Although their discussion of Rodrigo’s dating adventures provided one of the interview’s funniest moments, the conversation also highlighted the mutual admiration between the two singers.
Rodrigo credits Roan with helping inspire the confidence behind “expectations,” while Roan appreciates the creative freedom and support that Rodrigo brought to their collaboration.
Together, they’ve turned a friendship filled with candid conversations, musical inspiration and a little unsolicited romantic advice into a pop partnership that celebrates individuality and self-expression.
