Watching “Rosaline” one can’t help but think of the Shakespeare-inspired or period-set films aimed at teens in the late-’90s, like “10 Things I Hate About You” or “Ever After” to name just a couple. They are smart, often stridently feminist through their character’s actions not just their words, and they don’t talk down to their audience or feel the need to make the source material “hip.” Yet, somehow Karen Maine’s latest film, based on a young adult novel by Rebecca Serle, achieves none of those feats. This comes at an even greater disappointment considering the sharp authenticity of Maine’s previous coming-of-age film “Yes, God, Yes.”
Much of the film’s script, from “(500) Days of Summer” scribes Scott Neustadter and Michael H. Weber, relies on the titular character’s supposed sarcastic wit. Yet, Kat Stratford, she is not. Kaitlyn Dever is capable of such depth and nuance (see “Short Term 12”), but here she is given fetid material. Where Julie Stiles’ Kat and Drew Barrymore’s Danielle have personalities that push them to break free from their cages, Rosaline’s entire personality is just the longing for that freedom. Who is she? There’s a dashed off line about wanting to be a cartographer, yet she is never shown engaging with maps or doing anything really that isn’t driven to move the plot forward. 
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Rosaline, of course, is Juliet’s cousin and Romeo’s ex with whom he was supposedly in love before the star-crossed meeting that would end two young lives. This being a teen film – spoilers – no one dies. Rather, all the teen girls hoodwink the adults and learn to stop fighting over boys (because boys are ridiculous buffoons and passion doesn’t last, don’t you know?).
In a desperate attempt to “update the material” for Gen Z, yet in a manner that feels right out of the worst kinds of early-2000s films, Rosaline has a flaming GBF (gay best friend), Paris (Spencer Stevenson). At one point, he has to stifle a prolonged “yassss,” and I swear my soul left my body. There might have been an interesting way to tackle what it was like to be gay in this era, but this film is not interested in honestly tackling anything about this era – or fully sticking with a wholly anachronistic style either. Gone are the days of clever subversions like “A Knight’s Tale.”
Rosaline’s father, bafflingly played by Bradley Whitford, not knowing her secret relationship or the drama with Romeo, wants to marry Rosaline off. The first suitor (Lew Temple) has a Southern accent, which would be harmless if it was not played to indicate he is an oaf, that he is lesser than the fair Rosaline. It’s jarring enough that this film has a mish-mash of American and British accents, but to perpetuate the coded idea that a Southern accent makes a person immediately not worthy of your time and unequal intellectually is not only insensitive, it’s potentially dangerous. 
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The film is not completely without its charms, however. The cinematography by Laurie Rose (“Catherine Called Birdy,” “Summerland”) is sumptuous, awash in golden light during daytime hours and beautiful blue hues during night scenes. The costumes from ​​Mitchell Travers (“The Eyes of Tammy Faye,” “Hustlers”) are luscious and ornate, especially Rosaline’s many elaborate gowns. One crimson gown that she wears while crossing a murky river in particular is a showstopper.
Another light in the midst of this abysmal film is Sean Teale (“Skins”) as Dario, Rosaline’s main love interest, who is incredibly charismatic. That Teale is at home in the flowery language more in line with the setting underscores just how jarring and off-putting the anachronistic language is. However, his charisma can only go so far when Dever has, it seems, been directed to withhold any chemistry or inkling of an attraction towards him until the very end of the film. What makes these opposites attract films so delicious is the tension that arises when attraction takes a character off guard, ever so derailing whatever course they thought they were on. This film withholds any such pleasures.
And what of Juliet (Isabela Merced, “Dora and the Lost City of Gold”) and her Romeo (Kyle Allen, “The Greatest Beer Run Ever”)? They are of course infantilized, as the script’s idea of subversion is to show they were actually teenagers in the original play. Never mind that the whole concept of teenagers is a 20th-century invention and that people of their age in Medieval Verona were essentially considered adults already, chattel for land or money or title exchanges through marriage. These were concepts “Ever After” understood and worked into its plot, and the contemporary-set Shakespeare adaptations of the ’90s wisely side-stepped by setting the action in modern-day high school. 
“Rosaline” comes on the heels of several films aimed at teens and young adults that dumb down source material, favor plotting over characterization, and think rebellion in and of itself is a personality. Perhaps a comedic riff on one of the great tragedies ever set to the page, especially one that treats the world as if it were IP, was doomed from the start. Alas, it seems this sort of uninspired, insipid drivel is all audiences can expect from studios anymore. [D+]
“Rosaline” debuts on Hulu on October 14.