Rosaline: Yassified Shakespeare through a Nostalgic Millennial Lens

By Trevor Boffone and Danielle Rosvally

June 12, 2023

Romeo and Juliet have significant cultural capital. Shakespeare’s infamous star-crossed lovers have long held a prominent place in popular culture, especially in cinema. Mainstream films such as the landmark West Side Story (1961), Baz Lurhmann’s hyper contemporary Romeo + Juliet (1996), the animated Gnomeo and Juliet (2011), and the quirky paranormal zombie rom-com Warm Bodies (2013) have kept Romeo and Juliet at the forefront of our collective popular imagination. This begs the question: with an abundance of Romeo and Juliet adaptations, do we really need another one? 

The 2022 film Rosaline is based on Rebecca Serle’s 2012 young adult novel, When You Were Mine. Rosaline remixes Shakespeare’s Romeo and Juliet from the point of view of Romeo’s shunned ex-girlfriend, Rosaline, who just so happens to be Juliet’s literal cousin. Directed by Karen Maine with a screenplay by Scott Neustadter and Michael H. Weber, Rosaline was released on Hulu on October 14, 2022. The film quickly captured the interest of fans of Shakespeare and teen rom-coms, and especially the confluence of these two groups. While Rosaline is surprisingly faithful to Shakespeare’s play, the film shifts the narrative to focus on Rosaline and to re-write the play’s infamously tragic ending. What if Romeo and Juliet don’t die? What if Romeo and Juliet aren’t even the main characters of the story? This is precisely where Rosaline intervenes. 

In some ways, it’s odd to see yet another adaptation of Romeo and Juliet (debatably the most adapted piece from Shakespeare’s canon, alongside Hamlet). Rosaline is a  remixed adaptation that feels slightly out of place in 2022, partly because it is so engaged with nineties and aughts nostalgia. The film aesthetically borrows from nineties/aughts rom-coms, keeping with other Shakespearean adaptations of that time—10 Things I Hate About You (1999), She’s the Man (2006), etc. This makes us wonder: while the film feels like a young adult romance, is the intended audience actually young people? Or is it the elder Millennials whose nostalgia feeds the callbacks with which this piece is engaged? When we zoom out to look at Rosaline’s contemporary peers (the fall 2022 release of Hocus Pocus 2 and the opening of the musical & Juliet on Broadway), Rosaline falls directly in line with the popular culture of the moment which has elements for both elder Millennials and their (gulp) children.

Other elements of Rosaline pay tribute to the popular culture we grew up with. The soundtrack features remixed covers of nineties/aughts pop including Céline Dion’s “All by Myself” and “It’s All Coming Back to Me Now,” and Enrique Iglesias’s “Hero.” Shakespeare’s character Paris is transformed into Rosaline’s queer best friend and one can’t help but reminisce about the truly nineties YouTube series Sassy Gay Friend. Kyle Allen as Romeo is so reminiscent of Heath Ledger in A Knight’s Tale (2001) that we can’t help but think of him as “dollar store Heath Ledger.” The plot follows the nineties rom-com formula: happy but completely mismatched couple torn asunder by circumstances that involve a double meetcute as they find others more suited to them. She can’t stand the new guy she’s met, though he’s clearly a much better fit for her than the original guy, and he slowly becomes more palatable to her as the piece unfolds. Shenanigans ensue that almost ruin everyone’s happy ending, but a quirky side character with MacGuffin-shaped abilities saves the day. The film is coded to Millennial sensibilities about what a rom-com is using nostalgic tropes and background music tuned to our ears.

Much like the musical & Juliet, Rosaline’s primary goal seems to be giving Shakespeare’s female characters more agency and better storylines with more gender equality. In Rosaline, we have the titular main character who is definitely a strong female protagonist. She has goals, aspirations, dreams, and vocally opposes the patriarchal structures of her society (talking back to her father, criticizing the constraints her Verona places on women, and taking Juliet out for a night on the town where her goal is to have fun at the expense of the men around her). We also have the character of Rosaline’s nurse: an actual nurse with medical credentials who went to school to be an RN (and reminds the audience of this several times throughout the film before ultimately saving the day at the very end of the movie).

The film succeeds as a piece of lighthearted entertainment. It offers wish fulfillment to everyone who’s ever sat through a high school English class wondering why the main characters in Romeo and Juliet couldn’t have just taken a little more time to work through their communication issues. It offers more agency for the play’s female character. It takes loose ends that Shakespeare created (leaving the character of Rosaline hanging, why the mail in Verona is so unreliable—thanks Steve the stoned courier) and ties them up. It gives Romeo and Juliet the happy ending that audiences have craved so badly throughout history that for a period of about a hundred years the play was performed with an alternate ending where the lovers get to embrace in the tomb before the poison sets in. Rosaline presents us with a new romantic leading man who has wit, the ability to be poetic, and, of course, washboard abs (Dario played by Sean Teale).

Predictably enough, it doesn’t take much to shift Shakespeare’s tragedy into a nostalgic rom-com. Besides creatively re-imagining a few side characters, the film only changes four major plot points from Shakespeare’s original: it creates space for Juliet to announce her marriage to Romeo in the town square after he kills Tybalt, the play’s ending is re-written significantly (obviously), Friar Laurence and his sundry contributions are 86ed or re-directed to other characters, and the film seems to ret-con over the fact that Romeo kills Paris on his way in to the Capulet tomb (while this particular plot point isn’t specifically addressed, it’s difficult to envision dollar store Heath Ledger stabbing sassy gay Paris to death).


This brings us back to our original question: do we really need another adaptation of Romeo and Juliet? We say a definitive yes. Rosaline connects to a larger cultural trend of what we call “Yassified Shakespeare,” or contemporary remixes of Shakespeare’s plays that queer themselves in the process of adaptation. These yassified appropriations rework Shakespeare’s cultural capital with a genre-specific, hyper-contemporary aesthetic. 

Rosaline reveals the dexterity and universality of the Shakespeare canon. There is a reason why writers keep returning to Shakespeare to not just re-imagine early modern theater but also to speak to our current moment. As elder Millennials, we came of age at a time when few nuanced portrayals of feminist agency reached mainstream cinema. Films such as Rosaline correct that narrative, allowing us to re-imagine the world of Romeo and Juliet to be one that goes far beyond the titular characters. While Shakespeare may not have given Rosaline much of a narrative, Rosaline offers viewers an entry-point into Shakespeare’s canon that’s fun, engaging, and more empowering than Shakespeare’s original.