When Ilana Wolpert imagined her life, she pictured much of it tucked away in a library, analyzing the works of Shakespeare after earning her PhD in English. Instead, she’s days away from walking the red carpet for her feature screenwriting debut Anyone but You, a modern-day romantic comedy inspired by Much Ado About Nothing that stars Sydney Sweeney and Glen Powell. Wolpert uprooted her own trajectory during her senior year of college, when she opted to enroll in a screenwriting class. It was love at first sight. “Everything clicked,” she tells Vanity Fair, “I haven’t looked back since.”
After her collegiate meet-cute, Wolpert moved to Los Angeles, where she worked as an assistant to Rachel Bloom on The CW’s Crazy Ex-Girlfriend and then secured a plum staff writing position on High School Musical: The Musical: The Series. “I met some of my best friends writing on the show, met my girlfriend writing on the show,” Wolpert says, referencing Tony-nominated cast member Julia Lester. But during breaks from production on the Disneyfied teen series, Wolpert devoted herself to her passion project: an R-rated romantic comedy she wrote in her parents’ Utah home mid-pandemic. Often she’d work next to her dog Ella, who snoozes behind Wolpert during our Zoom interview. “I missed my friends. I missed weddings. I wanted to fall in love,” she remembers. The film “was an escapist fantasy for me.”
But what resonated with Sweeney, who was the first to board the project as an executive producer, was the realistic uncertainty that plagues protagonists Ben and Bea (named for Much Ado’s Benedick and Beatrice, naturally). Like Wolpert, Bea upends her plans by withdrawing from law school and getting “deprogrammed” from the idea of marriage, despite childhood Halloweens spent dressing as a bride.
“One of the things that we talked about is this pressure in your mid-to-late 20s to have your life look a certain way, to know what your career is going to be, who you’re going to be with,” Wolpert says. “When we first met, we were in the place of all of our friends getting married, dealing with people trying to set me up or meddle in my life because they think that, to be happy, you need to be in a relationship…. She just totally got that.” And even as Sweeney’s star status soared with dual Emmy nominations for Euphoria and The White Lotus, Wolpert says that she always made room for the movie. “It would not exist at all without her,” she says.
Just as it did with May December’s Samy Burch, what started as a first-time film writer’s spec script morphed into a major motion picture once big names got attached. This time, they were Top Gun: Maverick’s Powell and director Will Gluck, whose own film Easy A was inspired by classic literature in Nathaniel Hawthorne’s The Scarlet Letter. Persistent discourse about the state of the rom-com is “a little tiresome,” says Wolpert, but the fact that hers is getting a prime Christmas release is a promising sign.
“What I’m grateful for is that both Sydney and Glen were so down for a rom-com. There are not a lot of people in their age demographic, actors of any gender, who wanted to do rom-coms—at least from early stages when we were exploring the cast,” she adds. But Wolpert doesn’t consider it “a dying genre.” In fact, she’s set her sights on tackling a queer rom-com next.
“I really just wanted my life to look like a romantic comedy,” says Wolpert. Evidence of her lifelong adoration is all over Anyone but You, from a Titanic-referencing scene, to perhaps the most consequential grilled cheese since Nate’s burnt beauty in The Devil Wears Prada.
Wolpert drew inspiration from Much Ado About Nothing, which she calls “the perfect enemies-to-lovers story,” as well as other modern works based on literary classics, including Clueless (loosely based on Jane Austen’s Emma), 10 Things I Hate About You (born from Shakespeare’s The Taming of the Shrew), and She’s the Man (from Shakespeare’s Twelfth Night). “The sense of farce, especially in She’s the Man, was something that I really leaned into and loved when it comes to Bea and Ben getting tricked into being together,” Wolpert explains. “That incredible scene where Amanda Bynes goes to the carnival and is running around and trying to be two people at once—I loved that sense of physical comedy too, which we have in Anyone but You.”
Like other faithful students of the rom-com, Wolpert classifies herself as a Nora Ephron devotee, referring to 1989’s When Harry Met Sally, 1993’s Sleepless in Seattle, and 1998’s You’ve Got Mail as “my holy trinity.” Wolpert continues: “She just so effortlessly made you fall in love with those characters and the conflict really came from a place of character…. But I definitely saw [the movies] at too young of an age on a cable channel I probably shouldn’t have been watching,” she adds with a laugh.