On October 13th, popstar besties Olivia Rodrigo and Chappell Roan made an Instagram post teasing the release of the upcoming “expectations” collab and accompanying music video. The photo shows both Chappell and Olivia in 80s inspired get-ups, including big hair, bright makeup, and chunky jewelry, in a yellow convertible with “XPECT8NS” on the license plate. The “expectations” remix marks the first official song feature between the two artists. The single and music video are set to be released on Thursday, October 15th, according to the Instagram caption. Fans unleashed a flood of excitement for the collab in the comments under the announcement.
The lyrics of “expectations” from Olivia Rodrigo’s third album, you seem pretty sad for a girl so in love, express that she “won’t settle for a guy with a fake job” and their “indecision is painfully unattractive,” a sentiment similar to that of Chappell Roan’s 2023 singles “Femininomenon” and “Super Graphic Ultra Modern Girl.” Both of these singles detail multiple failed dates with disappointing men, with the latter noting her date “wouldn’t dance” and “didn’t ask a single question.” It’s safe to say that “expectations” tells the story of an all-to-common experience for young women on the dating scene.
This song and music video come after Olivia and Chappell’s history of collaborations and supportive interactions. In 2022, Olivia Rodrigo invited Chappell Roan to open for her on her May 27th date of the SOUR Tour. In 2022, both popstars were still on the rise, as Chappell had not released her breakout single yet, and Olivia was still promoting her first album, “SOUR.” Collaborations between Olivia and Chappell continued into 2024, where Chappell served as an opening act for the first 24 dates of Olivia Rodrigo’s GUTS World Tour and provided backing vocals on several GUTS tracks, including “Lacy,” “Get Him Back!,” and “Obsessed.” These backing vocals and added harmonies prove that the “expectations” collab is far from the first time Olivia and Chappell have worked together in the recording studio.
In June 2026, Olivia Rodrigo announced Daisy Chain Fields, an all-women music festival that donated its net proceeds to charities dedicated to advancing and advocating for women and girls. The festival hosted its inaugural date on August 29th, 2026, in Irvine, California. Olivia Rodrigo was inspired by Lilith Fair to create and found Daisy Chain Fields. Lilith Fair was a music festival founded by Sarah McLachlan that took place between 1997 and 1999. Much like Daisy Chain Fields, Lilith Fair’s artist lineup featured all female artists and female-led bands. Despite only running for three years, Lilith Fair generated 10 million dollars to be donated to charity. Daisy Chain Fields was able to top this huge achievement by generating 20 million dollars from its August 29th date, all of which was donated to women-focused charities. Some of the charities that Daisy Chain Fields donated to include the Center for Reproductive Rights, Johns Hopkins Center for Indigenous Health, National Women’s Law Center, and Planned Parenthood.
By founding Daisy Chain Fields, Olivia Rodrigo sought to fight against sexism in the music industry and support women’s reproductive rights and safety in the process. Olivia considers herself to be a feminist and has repeatedly proclaimed being “really passionate about women’s rights and reproductive healthcare,” which was a big reason for her creating the benefit concert. The popstar also expressed that she views all of the women on the lineup to be friends and heroes of hers. After the massive success of the festival, Olivia and Chappell posed together for Rolling Stone’s cover story on the event. Also included in the cover spread were American singer, rapper, and dancer Doechii and Canadian singer-songwriter Sarah McLachlan, both of which appeared at Daisy Chain Fields.
With the release of the music video, “expecations” featuring Chappell Roan will become the fourth single from you seem pretty sad for a girl so in love, following “drop dead,” “the cure,” and “stupid song.” The remix comes in the midst of Olivia Rodrigo’s hugely successful Unraveled Tour, spanning 86 shows across North America and Europe. In familiar fashion for Olivia, a portion of the proceeds from the Unraveled Tour ticket sales are being donated to the Fund 4 Good Initiative that supports the futures of women and girls.
Will you be streaming “expectations” featuring Chappell Roan?