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February 05, 2019 at 05:14 PM EST

Every day until Valentine’s Day Entertainment Weekly is celebrating our special romantic comedy-themed Untold Stories issueCheck out all of our behind-the-scenes tidbits, reunions, and oral histories here and follow #LoveEWstyle on Twitter and Instagram

As someone who has been in her fair share of romantic comedies, Julia Stiles has some thoughts on one thing that every rom-com needs. “For starters, the key to a good romantic comedy is that the people making it know that they’re making a romantic comedy,” Stiles says. “The makers of it have to have a sense of humor and not take themselves too seriously but also not be dumb about it and not pander to the audience. I’m a romantic at heart and I love to see two people get together at the end of a movie despite their circumstances.” She then adds, with a laugh, “But you never want to be in a romantic comedy that thinks it’s a drama and the audience thinks it’s a comedy.”

In honor of Stiles’ impressive rom-com career, EW had her look back at four of the roles that cemented her as an expert in the genre.

10 Things I Hate About You (1999)
Stiles was 17 when she filmed this adaptation of Shakespeare’s The Taming of the Shrew, in which she played Kat Stratford, a moody high schooler who fell for Heath Ledger’s Patrick Verona. “I was desperate for the part,” Stiles remembers. “It was so refreshing to see a teenage girl who was so feisty. I thought that the writers had a healthy dose of cynicism with their humor that you don’t always find with teen romantic comedies.” And it seemed like the perfect fit for Stiles, who was sick of hearing the same thing at auditions. “I was an auditioning actor and mostly I would go out for commercials and they would tell me that I wasn’t bubbly enough,” she continues. “They always thought I was angry so to read a part like Kat I was like, ‘Ah, this is perfect for me!'”

Down to You (2000)
Stiles starred alongside Freddie Prinze Jr. as college sweethearts Imogen and Al in this film about the power of first love. “The movie changed a lot from the development process to the finished product,” Stiles says. “[Writer/ director] Kris Isacsson had a vision for it that was a lot darker, so I remember thinking it was really mature. Then Harvey Weinstein and Miramax ended up producing it and turned it into a movie that was much more of a commercial, upbeat romantic comedy, for better or worse.”

Carolina (2003)
More than playing the titular Carolina in this rom-com, Stiles remembers the experience of making the movie with co-star Shirley MacLaine. “That movie almost didn’t get made because it was a low-budget indie and the financing fell through at different times,” she says. “But Shirley MacLaine really fought to get it made and I just remember totally idolizing her. She had so many amazing stories about her life. I could’ve spent all my time just listening to her.”

The Prince & Me (2004)
“The romantic comedies that do it well are the ones that can still use the tropes but reinvent them or make them feel new and refresh the mold.” That’s what Stiles says of this outing, in which the actress played Paige Morgan, a pre-med student who can’t be distracted from academics when she meets Eddie (Luke Mably), a seemingly harmless (and somewhat clueless) man who turns out to be the Prince of Denmark. “The Prince & Me was a Cinderella story flipped on its head in that Paige had her own goals and wasn’t just out to marry a prince.”

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