Stratford Sisters Reunite: Julia Stiles and Larisa Oleynik Reflect on 10 Things I Hate About You

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The Stratford sisters are back—well, at least for one unforgettable night. The iconic duo from 10 Things I Hate About You, Julia Stiles (who played the fierce and independent Kat Stratford) and Larisa Oleynik (the sweet and popular Bianca Stratford), reunited at a special screening of Wish You Were Here in New York City. And here's the kicker: Stiles, who is a director now, actually helmed Wish You Were Here, adding a whole new level of excitement to their reunion.

For those who might need a quick refresher, 10 Things I Hate About You was released back in 1999 and quickly became a teen classic. The film was a modern, witty spin on Shakespeare's Taming of the Shrew, set in a high school where family drama, teenage angst, and romance collide. The film starred an incredible ensemble cast—besides Stiles and Oleynik, it featured the late Heath Ledger, Joseph Gordon-Levitt, Gabrielle Union, and Andrew Keegan. The plot revolves around Bianca, who’s not allowed to date until her older sister Kat does. Enter Cameron (Gordon-Levitt), who wants to date Bianca and persuades Patrick (Ledger) to date Kat, a girl who clearly has no interest in being set up. Of course, this leads to a whirlwind of complications, laughs, and ultimately, romance—because in a good teen movie, love always wins in the end.

That unforgettable mix of teen rebellion, love, and humor made 10 Things I Hate About You a massive hit. And let’s not forget the iconic moments—like when Patrick serenades Kat on the high school football field with Can't Take My Eyes Off You. That moment was so memorable that it was parodied in Not Another Teen Movie just a couple of years later. It was a performance so magnetic that Ledger won the MTV Movie Award for Best Musical Performance in 2000, which just goes to show how much that scene resonated with fans. Stiles herself snagged the MTV Movie Award for Breakthrough Female Performance, cementing her place as one of Hollywood's rising stars at the time.

But enough about the film—let’s talk about the actresses themselves. Even though 10 Things I Hate About You was a game-changer for both of them, it’s interesting to hear how Stiles and Oleynik reflect on their roles all these years later. Stiles, now 43, said she was absolutely thrilled to reconnect with Oleynik at the Wish You Were Here screening. In an interview with PEOPLE, Stiles explained that while it’s hard to keep in touch with people in the whirlwind of life, she and Oleynik had managed to stay connected through text messages. As Stiles put it, “It’s just that thing—when you have these people in your life, but you don’t always see them in person.” But when they do reunite, it’s like no time has passed at all.

Stiles has certainly kept herself busy since 10 Things I Hate About You. She’s starred in major films like Jason Bourne and Hustlers, proving her range as an actress. But despite all her success, Stiles admits that Kat Stratford is still the role she’s most often recognized for. And she’s completely fine with that. She even went on to explain how Kat was the character she’d always wanted to play. “I was a 17-year-old actress auditioning for roles, and I kept getting told, ‘You’re too serious,’ ‘You need to smile more,’ or ‘You need to be sexier.’” As a young woman, Stiles was still figuring out who she was, and those comments really got to her. But when she read for 10 Things I Hate About You, Kat was everything she had been waiting for: a smart, fierce, and unapologetically outspoken girl who didn’t care what anyone thought. For Stiles, stepping into Kat’s shoes felt like a big victory and gave her a sense of strength and identity. “It meant a lot,” she said of her role, adding that it was even more fulfilling to know that the character still resonates with fans today.

Stiles’ thoughts on her time playing Kat show just how significant the role was in her career and in her personal growth. It wasn’t just a job; it was a transformative experience. And judging by the continued love for the movie, it’s clear that 10 Things I Hate About You left an indelible mark on fans, too. The movie wasn't just a typical teen flick; it was filled with raw emotion, hilarious one-liners, and—let's not forget—some seriously swoon-worthy romance.

As for Oleynik, who portrayed the ever-charming Bianca, she’s also made her mark in the entertainment world. After 10 Things I Hate About You, she went on to have a successful career in television, appearing in hit shows like Mad Men, Pretty Little Liars, and Hawaii Five-O. She, too, has a solid fan base, with people still remembering her as the lovely and lovable Bianca. It’s no surprise that she and Stiles have remained close over the years, with both actresses continuing to embrace their 10 Things I Hate About You legacy.

One of the most intriguing aspects of the 10 Things I Hate About You phenomenon is the lasting impact it has had on its audience. It’s been over 25 years since the movie was first released, but its themes of sisterhood, self-discovery, and the complexities of love still hit home. The film’s clever dialogue and unforgettable characters have made it a classic, and it’s easy to see why people still hold it near and dear. Whether it’s Kat’s fiery independence, Bianca’s charm, or the swoon-worthy chemistry between Kat and Patrick, there’s something in the film for everyone.

Looking back on the success of 10 Things I Hate About You, it’s clear that it was more than just another teen rom-com. It was a cultural touchstone that helped shape an entire generation’s understanding of love, friendship, and identity. And even as the cast has gone on to pursue different paths in their careers, the movie remains one of the most beloved teen films of all time.

As the Stratford sisters continue to celebrate the legacy of 10 Things I Hate About You, it’s evident that this film, with its perfect blend of humor, heart, and romance, will always have a special place in pop culture. The reunion of Stiles and Oleynik at the Wish You Were Here screening is just another reminder that, no matter where life takes you, the bond between these two actresses—and their characters—will always be something special.

So, while 10 Things I Hate About You may have come out in a different era, its themes and characters still hold up. The movie continues to inspire new generations of fans, reminding us that no matter how much time passes, some things—like sisterhood, love, and the iconic moments of a great film—never fade.