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When you think about the female stars of late ’90s, early aught rom-coms, a cluster of names come to mind: Julia Roberts, Drew Barrymore, Cameron Diaz, Renée Zellwegger, Jennifer Lopez. And then there was Julia Stiles. She was the younger version of these hapless women charting the bumpy terrain of their nascent professional lives and romantic relationships. She was where they started, and her presence in the (mostly) high school rom coms of the era was near unavoidable. She landed her breakout role as angsty teen feminist Kat in 10 Things I Hate About You, starred as Juilliard-aspiring ballet dancer Sara in Save the Last Dance, played Paige, a pre-med student who falls for a prince in The Prince Me.
While rom-coms catapulted her to fame, Stiles has actually accumulated a far more diverse IMDB page than we might give her credit for. She took on roles in romantic thrillers (O) in horror films (Orphan), in dramedies (Dexter) and situational comedy (The Lake). So it makes sense that, decades after her career took off, she wanted to challenge herself with something else. “I had been looking for the right story to tell as a director for a really long time,” says Stiles.
For Stiles, that story is Wish You Were Here (yes, a rom-com), which follows the romance between a young woman (Isabelle Fuhrman) who has a whirlwind night with a man she discovers is terminally ill (Mena Massoud) and is out today. Here, Stiles opens up about what she learned about directing, the legacy of 10 Things I Hate About You, how she feels about Save the Last Dance, and the actress she dreams of working with.
Vogue: Why did you want to make Wish You Were Here your directorial debut?
Julia Stiles: I had aspirations to direct. I had done a couple of shorts, but I probably was also a little bit gun-shy, and then one of the actresses in the movie, Gabby Kono, who plays the best friend Helen [and] also produced the movie, she sent me the book, and I fell in love with it. I could totally visualize it as a film.
What did you love about the script?
I’m a romantic at heart. I love a good love story. I love the idea of love, falling in love, falling out of love, relationships, heartbreak and then triumph, but I recognized there’s a tradition of these kinds of stories. There’s the rom-com-y elements where her mom and best friend are pressuring the girl to go on a dating app and find the right guy and get her life together, and moments of that levity and silliness. Then the love story part of it, the tragic love story, to me, was so much more mature than the age of the main characters. They’re very young, but their love is a very deep and meaningful one. I was really lucky that the author, Renée Carlino, trusted me, and knew that I was trying to keep the spirit of her book, but I had to distill it for a film.
What did you distill?
This idea that there’s two versions of the love story, there’s the version that they have in reality, and then they have a version of their love that’s the love affair they dream of, and that we should be so lucky to make a lifetime of memories with another person.
You said you’ve always had a love for romance, and it’s not lost on me that much of the work you’re known for, particularly for millennials, are rom-coms. Why did a rom-com have to be the first project you directed specifically?
It didn’t have to be at all. It just felt right. I also was very aware of having made a lot of movies about romance. Because I’ve been part of those trends, I was really conscious that this kind of movie could so easily veer into the corny. And so, I was trying really, really hard to keep it relatable and grounded in some sort of truth. When you work on something as a director, it’s, at least, a year of your life; in this case, it was five. The story really has to last. It has to be something that you’re still interested in telling years later. Not only has that been the case with Wish You Were Here, but I feel like it’s gotten deeper and more meaningful in the years since we set out to make it.
What accounted for the five years it took for the film to come together?
I don’t think that’s terribly long for an indie movie, but it was longer than I expected. There were hiccups along the way. It takes a while to get something cast. Finally, we got all the financing in place, and we were ready to start shooting, and the SAG strike happened. So, we had to wait until that was done. It’s a tough marketplace for indie movies right now. At least, that’s what I was told.
What did you learn about being a director from this project?
I learned that I love it. I’m totally hooked. I learned that my skills as a mother came in really handy, because moms [or] women in general have to be very good at multitasking. You have to be good at managing a budget, you have to be good at managing your time, you have to take care of other people, but also nudge them in a certain direction. And you have to function well with very little sleep. There was a turning point for me the first couple days on set where I was like, “Oh, I know how to do this. I’ve been on film sets for 25 years. I’ve seen this. I can do this."
But then there was also a time where my script supervisor said to me, “You need to stop apologizing.” I had to switch from being a people-pleasing actress to the leadership role of a director where you can’t sit back and wait for people to tell you what to do. You have to dictate it, fight for your vision and fight for the things that you want. It sounds silly when I say it, but it was something that I felt in my body.
How do you feel like the rom-com genre has shifted since you starred in them at their peak in the early aughts?
Well, social media, and technology are a huge part of them now. You can’t have a movie about dating and romance without text messaging and computers. I tried to avoid that a little bit. There is still some text messaging and dating app service in my film. The idea of being ghosted is a big one for the main character; she feels like she has this amazing connection with someone, and then she never hears from him. But I didn’t want to be showing text messages or a phone screen a lot. So, I had to find a visual representation of their love affair, or their night together, and then their communication.
While a certain group of people may be most familiar with your rom-com work, you’ve really stretched your muscles in different projects. How did you avoid being pigeonholed?
Early in my career, I was all over the place, and I think I’m much more intentional now—certainly, in the last five, or 10 years. But it’s funny thinking in those terms because as an actor, when you’re first starting out [and] auditioning, you just want to get hired, even if it’s on something stupid. You just need someone to tell you like, “You should be doing this.” And if you have some more success, you maybe have a little more control over what you can do, but it’s largely going to be dictated by what’s successful. So, if you’re successful in a certain genre, that’s the genre that’s going to be offered to you. Early in my career I was unconsciously going, “Oh, well, there’s all these teen movie trends. I want to do this.”
But it also honestly came down to, “Do I feel like going to the Czech Republic for a month? Sure.” Or, “Is this a director that I want to work with? Great.” It was a lot more flighty or cavalier. And then I had a period of time where I had done a series of indie movies that I thought were really good stories, but they only went to festivals, and people didn’t really see them. Then, I worked on Orphan with Isabelle [Fuhrman), who is in Wish You Were Here, and I remember thinking, “I can’t do a horror movie. I don’t like watching them. I’m too chicken, but I love this character. It’s a great script. Okay. I’ll do it.” And then it was successful, and you’re only offered horror movies. So, now I’m more aware of trying to pivot—or what works for me, and what doesn’t.
Why does 10 Things I Hate About You hold up as a great rom-com?
Because I think the writing was so good. It was a really whip-smart team of female writers, Karen McCullah and Kirsten Smith, who in many ways — like [main character] Kat Stratford — didn’t bend their wit, humor and observation to trends. They were very much pioneering, and they were like, “This is our personality and our sense of humor and that’s what the movie is going to be,” and that authenticity, I think, is what audiences respond to.
Where do you think your character Kat is today?
Hopefully, a lot happier out of high school. She’s either touring in a rock band or lives in a cabin in Costa Rica, makes her own sourdough bread, and has no screens around her. And, she’s totally surfing.
That feels like it checks out. What’s your favorite memory of working with Heath Ledger on that film?
He was just such a bright light. He was such an energetic, kind force. He was very magnetic, very charismatic, and we all had a great time working on that film. I really am grateful that he was so kind to me. For my first experience being the lead in a big studio movie, and, particularly, in romantic situations, you have to really feel comfortable with the person that you’re acting opposite, and he very much made me comfortable.
I absolutely adored The Lake, and you got to show off your comedy chops in it. Is there a chance for a season three?
I loved working on that so much. I auditioned for it, because nobody believes me as a comedic actress, but I was like, “I’m funny. I can be funny, and I love this character.” And I’m glad they believed in me. It was so freeing working on that show, and, particularly, as Maisy-May, my character, because there’s no trying to pretend that [she’s] a good person. She’s very strategic, very driven, and it’s all about her. So, I could shed all of my politeness. I think it was a casualty of the strikes [or] of some major event, but it didn’t get renewed. It didn’t really have to do with the content, it had to do with some market placing.
Over the years, people poked fun at the dance Sara does that gets her into Juilliard in Save the Last Dance. How did you feel about that?
Well, first, I don’t read it, and I just insulate myself from that. But sometimes friends will tell me things and send me links. Like, for instance, the Olympic breakdancer Raygun, somebody in my family sent an email chain with, “Oh, look at this. Isn’t this hilarious?” And then I saw they were likening it to my dance in Save the Last Dance. And I was like, “Oh, guys, I think they’re making fun of me.” But I would hate to go through life so self-centered, and also when you’ve been acting for 25 years, you become so inoculated to rejection or criticism. I say that, and then I’m also feeling incredibly vulnerable with Wish You Were Here coming out because it is my creation. Also, the internet. There’s just so much out there. Like, I would be torturing myself if I read everything.
I’m critical of Save the Last Dance—not of the movie, but my work in it. But I treat myself with compassion. I’m like, “You put a lot of pressure on yourself, you were very young.” I was 19, and it was a big deal. It was hard. So, I try to focus on the good things, like, that people care about the movie still, and that’s enough.
One of my favorite rom-coms of yours is Down to You with Freddie Prinze Jr., which is set to celebrate its 25th anniversary in 2025. What’s your favorite memory from it?
Freddie was a delight. He’s a sweetheart and a very kind person. At the time, I appreciated that he was such a kind, gentle soul. He, I think, was a little bit shy about all of his fame. To be completely honest, it was an example of a movie that was a great script, and then Harvey Weinstein and Miramax got involved, and they took over the movie, and it became something else that I don’t think I was really happy with. But I was too young to do anything about it.
For instance, I think Save the Last Dance was popular at the time while we were filming, and Harvey Weinstein decided that I had to dance in Down to You. I don’t even remember if it ended up in the film. Or I don’t know if it was Save the Last Dance or the table scene in 10 Things I Hate About You, but for whatever reason, he decided I needed to be dancing in this movie, and it was stupid. It was really stupid. It was my first example of being in something that started off as a really good script, and then was taken away from the director to fit the trends of that time, and like I said about authenticity, I don’t think that works.
Wow. Do you have any other projects that you re planning to direct after Wish You Were Here, or will you focus more on acting?
I’m totally hooked as a director. I am looking for the next project. I don’t really know what it is yet, because, creatively, I’m just coming out of the experience of making Wish You Were Here.
And I do still want to keep acting. I love acting when it’s the right combination of director and script and story and the right group of people. I think you learn a lot about acting from being behind the camera and seeing what editing can do, and the next time I step on a set, and I’m acting, I will be so reverential to the director because I know what they’re dealing with.
In terms of future projects, are there any actors or directors you dream of working with?
I adore Amy Adams so much. She is amazing in everything that she does. I would love to work with her to just soak up some of that talent, and she seems like a really good person, too. Directors…there’s a part of me that would love to do a Christopher Guest movie just because I think that improv comedy would be so fun. Yorgos Lanthimos is a wild director, and he would be great to work with too.
Are there any types, or any genres you haven’t tried out that you want to direct in, or you do want to act in maybe one day?
I love the idea of doing comedies, particularly as an actress, because I feel like the energy that you carry into work every day is affected. And so, instead of having to be terrorized or going through some tragedy, I’d rather cultivate the energy of making people laugh and making myself laugh every day. As a director, I loved putting music to Wish You Were Here. Vanessa Carlton did our score with her husband, John McCauley, who is in the band Deer Tick. We sourced some existing songs, but I loved putting music over the picture. I love dance, and I love music, so, a part of me was like, “Maybe I would love to do a musical.” It would be really cool to take an existing album and write a story to it, and make a movie musical. Not like Broadway, more of the rock operas, or whatever.
Did you recruit Vanessa and John to do the music?
She and I have been friends for a long time. We went to high school together, and we weren’t really friends then because we were at a performing arts high school where we [were] all busy with our performing arts. But she and I became friends in our early twenties. She had the success of “A Thousand Miles,” I had success with 10 Things I Hate About You or Save the Last Dance, and we bonded over this very unique experience of fame. We stayed friends throughout many walks of life—being in our early twenties, dating, career ups and downs, and now being parents and having our own families. For a long time, she told me she was really interested in composing for film, so, of course, I reached out to her. And you add John McCauley into the mix, and they have such a nice balance as a duet.