Julia Stiles’ Hollywood Dating History Before Marriage

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During her breakthrough years at the turn of the century, Julia Stiles became the envy of countless teenagers. She was appearing in some of the era’s most beloved movies—and kissing a remarkable number of its biggest heartthrobs. On screen, the New Yorker played romantic leads opposite Freddie Prinze Jr. in “Down to You,” Sean Patrick Thomas in “Save the Last Dance,” Heath Ledger in “10 Things I Hate About You,” and Josh Hartnett in “O.”

Stiles also wound up dating several of her co-stars away from the cameras. Before marrying a man whose work takes place behind the scenes, the Golden Globe nominee was romantically linked to an acclaimed artist and was mistakenly accused of ending another Hollywood favorite’s marriage. As she returns to the dance floor for the 35th season of “Dancing with the Stars,” here is a closer look at Julia Stiles’ romantic history.

Kat’s emotional poem-reading in English class remains one of the most memorable scenes in the 1999 teen favorite “10 Things I Hate About You.” Stiles drew on her own romantic life while performing it—but the person she had in mind was not necessarily the co-star fans might expect.

In an interview with the Spanish-language web series Mirá a Quién Encontré, director Gil Junger revisited the scene. “That was maybe one of the most moving performance[s] I’ve ever seen,” he said (via Elle). “… It just killed me, it was so raw, honest, and vulnerable. I asked her, ‘Where did that come from?’ and she told me she was thinking about a person’s name who she was deeply in love with at the time.”

Junger later revealed that Stiles’ inspiration was not her on-screen partner, but Joseph Gordon-Levitt, a co-star with whom she shared very little screen time. “They were very, very attracted to each other which was cool,” he said. The director’s comments appear to be the first public confirmation from someone connected to the film, although Rolling Stone had referred to the “500 Days of Summer” star—who is known for guarding his privacy—as Stiles’ former boyfriend in a 2001 article.

Junger’s account also helped settle a long-running rumor about Stiles’ love life. During the Mirá a Quién Encontré interview (via Grazia), the director made clear that, despite years of speculation, Stiles did not date her “10 Things I Hate About You” love interest, Heath Ledger.

While explaining Stiles’ discreet relationship with Gordon-Levitt, Junger said, “I know, right? Isn’t that funny? She’s, like, professing her love to Heath, and she’s in love with the guy who’s waiting in his trailer to shoot the next scene.” Stiles and Ledger never turned their on-screen romance into a real-life relationship, but she continued to speak warmly about the actor, who died nine years after the film was released.

“He was amazing,” Stiles told E! News in 2025. “He was such a bright light. He just walked into a room and lit it up … He was very kind and generous to me. Which you know, when you’re an actress in your first leading role in a big studio movie, you need to feel comfortable with the other person.”

In a 2004 profile promoting Stiles’ West End appearance in “Oleanna,” The Guardian recalled a comment she had made years earlier about ending a relationship because her boyfriend did not appreciate the work of celebrated novelist John Steinbeck.

Stiles initially denied making the remark, then reconsidered. “Well, that can’t have been the only thing,” she said. “There must have been other stuff he was doing.” Gordon-Levitt might seem like the obvious candidate given the timing of their reported relationship during “10 Things I Hate About You,” but could another young star of the period have been the boyfriend who dismissed “East of Eden” and “Of Mice and Men”?

Rumors have also long suggested that Stiles briefly dated Joshua Jackson, who became famous as Pacey Witter on the teen drama “Dawson’s Creek.” Neither Stiles nor Jackson has confirmed or denied the speculation, leaving the alleged romance unsubstantiated. Here’s a look inside Jackson’s own relationship history.

Gordon-Levitt was not the only co-star from a Shakespeare adaptation whom Stiles dated around that time. She became romantically involved with Josh Hartnett after they were cast as Desi and Hugo, respectively, in “O,” the 2001 teen adaptation of Shakespeare’s “Othello.”

Hartnett, whose later dating history included Amanda Seyfried and Scarlett Johansson, eventually advised young actors against mixing romance and work. Speaking to Elle (via Grazia), he said, “You can make a lot of enemies in the business that way. But when you work with somebody every day, it’s like trial dating. You develop a fantasy about them. It doesn’t always work out, does it?”

Although the relationship did not last, Stiles and Hartnett remained on friendly terms. Nearly 25 years later, Stiles interviewed him for Interview magazine, and the former couple exchanged affectionate remarks. “You seem like you’ve created this wonderful life for yourself and I’m so happy for you,” Stiles told him. Hartnett replied that he would be glad to act in her next project as a director, adding with a joke, “It better be a good role.”

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Stiles returned to the romantic-comedy genre in 2004 with “The Prince and Me.” She played a college student who falls for a Danish royal posing as an ordinary student. Reports at the time suggested that she and co-star Luke Mably developed a romantic connection off-screen.

Stiles has never publicly confirmed a relationship with Mably, though she spoke warmly about him in several interviews. In a conversation with Live About, she praised his acting abilities and explained how he helped create their on-screen chemistry. “What was really great about him as an actor was that he was very unpredictable, and so it made me always have to pay attention to what he was doing,” she said.

There was, however, one moment when Stiles appeared a little frustrated with her British co-star. During a press conference call for the film, she expressed surprise (via The State Times) after Mably reportedly said they had done little rehearsal together. “The way I usually work is I like to bond with the person that I’m acting with so that we can feel like we trust each other and then,” she explained.

After her relationships with several actors, Stiles dated an artist in the mid-2000s. The “Save the Last Dance” star was in a two-year relationship with Jonathan Cramer, whom New York Magazine described as “Think Jackson Pollock, minus the self-destructive alcoholism.”

In 2006, Stiles spoke lovingly about Cramer during an interview with Marie Claire. “I’ve learned a lot from him, because he’s in a totally different creative profession,” she said. “And he’s a wonderful human being, and I’m madly in love.”

Stiles explained why she was reluctant to bring up his identity. “Because it would be weird to read about yourself in an article,” she said before further reasoning, “I would hate for him to think our relationship can be used to promote a film. You could see how he would hate that, right?” However, public appearances together at events such as the Lincoln Center Institute for the Arts in Education Annual Benefit, American Museum of Natural History’s annual Winter Dance, and Third Annual Whitney Museum Contemporaries Art Party and Auction meant little digging was required.

In 2010, Jennifer Carpenter filed for divorce from Michael C. Hall less than two years into their marriage. Inevitably, the rumor mill soon produced a theory about why their marriage ended so quickly. And the latter’s “Dexter” co-star was at the center.

Yes, Julia Stiles, who’d played serial killer survivor Lumen Pierce in the fifth season of the Showtime hit, was accused of having an affair with its leading man. The allegations were so loud she felt the need to quash them publicly. “I have absolutely nothing to do with the split between Michael and Jennifer,” the New Yorker insisted in a statement (via TMZ).

Stiles acknowledged that she and Hall enjoyed working together on “Dexter” and forged a friendship, but she was far from the homewrecker purported. “This is a personal matter between them, and we should respect their privacy,” she added. Here’s a closer look at what really happened between her and Hall.

Long before ex-wife Lily Allen single-handedly destroyed his reputation with the scathing “West End Girl,” David Harbour was dating a slightly less candid star, Julia Stiles. In fact, the pair dated for approximately four years!

Harbour and Stiles first got together in 2011 when they both lived in New York City. A year later, they worked together on “Between Us,” a film adaptation of Joe Hortua’s stage play about two married couples. But by 2015, shortly before Harbour’s profile went stratospheric thanks to “Stranger Things,” the couple went their separate ways.

It’s not known exactly why Harbour and Stiles split. However, the latter’s recent social media activity suggests that it wasn’t amicable. Alongside Milla Jovovich, Lily Rabe, and Florence Pugh, the “Down To You” star was one of many famous women who liked button on posts relating to Allen’s musical takedown. Here’s a closer look at Harbour and Allen’s relationship.

Julia Stiles’ love life got a happy ending in 2017 when she married cameraman Preston J. Cook. Far from the glitzy, star-studded affair you expect, “The Bourne Supremacy” star kept things simple, inviting just a couple of pals to the Labor Day ceremony on a Seattle beach.

The pair had first met while shooting “Blackway” three years earlier and got engaged in 2015, as she explained on “Live with Kelly!” “It was a total surprise,” she said (via Hello!) of the proposal. “Mostly because I talked myself out of it. We went on a trip to Colombia with his entire family over Christmas and New Year’s. So, because I’m a lady, I was like, ‘Do not ruin a perfectly good vacation by getting your hopes up. Just let it go. Be in the present moment.'”

The couple became first-time parents to son Strummer shortly after and later added another child, Arlo, in 2022,  then a third child, whose name is still unknown, two years later. These major personal life changes have had a positive impact on her professional, too. “My focus is less inward,” she told Romper. “I don’t go home and dwell on what I did at work that day, and I don’t lie in bed thinking about the scene coming up tomorrow and stress about it.” Here’s a further look at what Stiles is up to today.