Rosaline

In the great digital library of Alexandria we call "the streaming era," we were promised that everything would be available forever. Then 2023 happened, and suddenly, films started vanishing into thin air for the sake of corporate tax write-offs. One of the most stinging casualties of this "content purge" was Rosaline, a whip-smart, revisionist take on Romeo and Juliet that spent less than a year on Hulu before being banished to the shadow realm of digital VOD and gray-market physical copies. It’s a crying shame, honestly, because while the world doesn't necessarily need another Shakespeare riff, I’d argue we always need more movies that are this much purely-distilled fun.

I watched this while my neighbor was power-washing their driveway for three straight hours, and remarkably, the rhythmic shhhhh of the water against concrete perfectly underscored the movie's many scenes of frustrated characters waiting for slow-moving messengers. It was an accidental 4D experience I didn't ask for, but it weirdly heightened my appreciation for the film’s central gimmick: the logistics of a 14th-century romance are a total nightmare.

The Girl Shakespeare Forgot

The film centers on Rosaline, played by the perpetually underrated Kaitlyn Dever (who you might know from Booksmart or Dopesick). In the original play, Rosaline is the "other woman"—the girl Romeo is obsessed with for exactly five minutes before he sees Juliet and forgets Rosaline ever existed. Here, Rosaline isn't just a footnote; she’s a girl with a plan, a sharp tongue, and a very modern sense of self-preservation. When her cousin Juliet (Isabela Merced) starts swooning over the guy Rosaline thought was hers, she decides to sabotage the "greatest love story ever told" from the inside.

Kaitlyn Dever is the entire engine here. She plays Rosaline with a dry, cynical wit that feels like she accidentally wandered in from a 2020s indie comedy and is just waiting for everyone else to stop speaking in iambic pentameter. She’s not "likable" in the traditional sense—she’s manipulative, slightly selfish, and desperate—but she’s incredibly relatable. When she rolls her eyes at Romeo’s recycled poetry, she’s speaking for every person who has ever looked back at an ex and thought, "What was I thinking?"

A Tale of Two Romeos (and One Very Tired Courier)

The movie’s smartest move is its characterization of Romeo. Kyle Allen plays him as a well-meaning but utterly dim-witted hunk who falls in love with the first person who looks at him. My hot take? Romeo is a golden retriever with the IQ of a turnip. He’s not a romantic hero; he’s a guy who just really likes the idea of being in love, and Kyle Allen leans into the goofiness with a hilarious lack of ego.

Contrast this with the "arranged" suitor Rosaline’s father (Christopher McDonald, leaning into his classic "frustrated dad" energy) tries to foist upon her. Sean Teale plays Dario, a soldier who matches Rosaline’s wit bar for bar. Their chemistry is the secret weapon of the movie. While the Romeo and Juliet plot is the scaffolding, the "will-they-won't-they" between Rosaline and Dario is the actual heart. Sean Teale has that smoldering, effortless charm that makes you wonder why Hollywood hasn't handed him a major franchise yet. He’s the grounding force in a movie that occasionally flirts with being too chaotic.

Director Karen Maine and the screenwriting duo of Scott Neustadter and Michael H. Weber (500 Days of Summer) treat the source material with a playful irreverence. They know the audience knows how this ends, so they have a blast showing how close Rosaline comes to accidentally fixing everything. The historical inaccuracy isn't a bug; it's the whole damn point. From the pop-inspired soundtrack to the vibrant, borderline-anachronistic costumes, it feels alive in a way many stuffy period dramas don't.

The Tragedy of the Tax Write-Off

It’s hard to talk about Rosaline without mentioning its status as an "obscure" film—not because it’s an old, dusty reel found in a basement, but because it’s a victim of the modern industry’s volatility. Released in late 2022, it was a "Hulu Original" that received decent reviews but was unceremoniously yanked from the platform in May 2023. It’s now a "lost" film of the 21st century, accessible only if you're willing to hunt it down on digital storefronts.

This obscurity is a shame because Rosaline represents something we’re losing: the mid-budget, high-concept comedy that doesn't need to set up a cinematic universe. It’s just a 97-minute romp that knows exactly what it is. It even finds room for a delightful Minnie Driver cameo as the Nurse, who seems to be the only person in Verona aware of how ridiculous everyone is behaving.

If you can track this one down, do it. It’s a reminder that even the most well-worn stories can feel fresh if you just shift the camera a few degrees to the left. It’s light, it’s zesty, and it makes a compelling case for why the "ex" might have been right all along.

Rosaline succeeds because it refuses to take the "greatest romance of all time" seriously, treating Romeo like a fumbling teenager rather than a tragic icon. Kaitlyn Dever proves once again she can carry any tone, from heartbreaking drama to sardonic comedy, with total ease. It’s a breezy, clever piece of entertainment that deserved a much longer life on its original platform. If you’re tired of the same old tropes, give this jilted cousin a chance to tell her side of the story.