Love is a many-splendored thing, especially when you’re gawking at it from the outside. In this new column, we’ll be examining the celebrity couples—or, occasionally, friend pairs—who give us hope for our own romantic futures as we try to learn what we can from their well-documented bonds.
It has historically been a taxing (if not outright toxic) thing to be a young, female pop star; remember the “Britney vs. Christina” dichotomy that outright pitted two of the most famous female performers in the country against each other in the early aughts? Yet the long-standing friendship between Olivia Rodrigo and Chappell Roan flies in the face of all that.
Rodrigo and Roan have reportedly been friends since 2018, with the two singers working with music producer Dan Nigro early in their careers and Roan later opening for Rodrigo during her Sour tour in 2022. “I used to go visit her when she worked at a donut shop before she got signed, before she put out any of her music,” Rodrigo said of Roan on The Tonight Show with Jimmy Fallon in 2024.“I used to go and eat donuts with her and hang out. I’m so happy for her, she deserves the whole world.” (For the real LA pastry heads, the donut shop where Roan used to work is apparently Donut Friend in Highland Park.)
More recently, the two collaborated on a remix of Rodrigo’s song “Expectations,” an earworm-y bop that finds the two women in the all-too-familiar position of not wanting to date a guy or girl with a fake job. Rodrigo recently reported to Zane Lowe that when the two were working on the song’s second verse, and Rodrigo was relaying her romantic misadventures, Roan’s response was: “Oh my God, you need to start dating girls.” (I genuinely think every straight woman needs a lesbian bestie to be so appalled at how straight men are moving in 2026 that she actually raises said straight friend’s standards!)
But Roan is, of course more than just Rodrigo’s designated gay confidante. I love that both their dating woes are explored on “Expectations,” mostly because if I hear one more heterosexual express their unfounded opinion that “queer dating must be, like, so much easier,” I am going to fling my laptop across the room. (As Roan’s verse on “Expectations” proves, women can have fake jobs and flake on you, too! It is, as Roan sings, “classic LA behavior,” I fear!)
To borrow a phrase from Rodrigo’s earlier work, it’s brutal out here—not only for young women attempting to date, but also women of any age in the public eye—and I, for one, am really glad that Rodrigo and Roan are leaning on each other to make art, eat donuts, and complain about being ghosted. Isn’t that the true meaning of friendship, no matter how famous you both are?