Before Marriage, Julia Stiles Had Quite The Dating Track Record In Hollywood

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Julia Stiles became the envy of practically every teenage girl during her breakthrough period at the turn of the century, not only for starring in some of her generation's most-loved films, but for the number of heartthrobs who she got to lock lips with. Indeed, the New Yorker played the love interest of everyone from Freddie Prinze Jr. ("Down to You") and Sean Patrick Thomas ("Save the Last Dance") to Heath Ledger ("10 Things I Hate About You") and Josh Hartnett ("O").

As it turns out, Stiles ended up dating several of her male co-stars in real life. And before settling down with a man whose talents are behind-the-scenes, the Golden Globe nominee also had a relationship with an acclaimed artist and was wrongly accused of breaking up the marriage of another Hollywood favorite. As she once again gets to showcase her moves on the 35th season of "Dancing with the Stars," here's a look at her eventful romantic past.

The moment when Kat reads her poem in English class is one of the most emotionally powerful in the 1999 teen classic "10 Things I Hate About You." The actor who played her, Julia Stiles, drew on her romantic experiences at the time with a fellow cast member. But it's not necessarily the one you'd expect.

In an interview with Mirá a Quién Encontré, a Spanish-language web series, director Gil Junger recalled the scene. "That was maybe one of the most moving performance 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.'"

The filmmaker then confirmed that the creative inspiration wasn't her on-screen love interest but a co-star she'd had practically no screen time with, Joseph Gordon-Levitt. "They were very, very attracted to each other which was cool," he added. Although this appears to be the first time anyone associated with the film has explicitly spoken about the brief romance in public, Rolling Stone magazine did reference the "500 Days of Summer" star — who's also renowned for keeping his private life private — as Stiles former boyfriend in a piece published back in 2001.

Gil Junger's tell-all interview about the dating habits of his "10 Things I Hate About You" leading lady also finally put a persistent rumor to bed. Speaking to the web series "Mirá a Quién Encontré" (via Grazia), the director confirmed that contrary to popular belief, Julia Stiles never had a romantic connection to her on-screen love interest, Heath Ledger.

While discussing the former's hush-hush relationship with another co-star, Joseph 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." But although life never imitated art for Ledger and Stiles — who played high schoolers Patrick Verona and Kat Stratford — the latter still has nothing but love for the former, who tragically died nine years after the film's release.

"He was amazing," Stiles recalled to 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."

While profiling Julia Stiles to promote her performance in the West End play "Oleanna" in 2004, The Guardian referenced a comment she made years earlier about a former boyfriend, one she'd apparently given the heave-ho simply for failing to appreciate the works of celebrated author John Steinbeck.

"Well, that can't have been the only thing," Stiles protested after initially insisting that she'd never made such a remark. "There must have been other stuff he was doing." While Joseph Gordon-Levitt would appear to be the prime suspect due to the timeline — the pair had secretly dated while they were shooting "10 Things I Hate About You" — could another young pin-up from the same era have been responsible for snubbing the likes of "East of Eden" and "Of Mice and Men"?

After all, rumors have continued to circulate that Stiles briefly dated Joshua Jackson, who shot to fame playing Pacey Witter in the teen melodrama "Dawson's Creek". Neither party has confirmed or denied the speculation, so it remains a mystery. Here's a look inside Jackson's own relationship history.

Joseph Gordon-Levitt isn't the only co-star from a Shakespeare adaptation Julia Stiles dated at the turn of the century. She dated Josh Hartnett after the pair were cast as love interests, Desi and Hugo, in 2001's Othello retelling "O."

Several years later, Hartnett — whose dating history also includes Amanda Seyfried and Scarlett Johansson — told Elle (via Grazia) that he couldn't recommend mixing business with pleasure to any actors starting out: "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?"

Things might not have worked out romantically between Hartnett and Stiles, but they have remained friendly. Nearly a quarter-century later, the Stiles interviewed Hartnett for Interview magazine. And both had nothing but kind things to say. "You seem like you've created this wonderful life for yourself and I'm so happy for you," Stiles gushed. In response, her ex stated that he'd be happy to lend his talents to her next directorial effort. He joked, "It better be a good role."

In 2004, Julia Stiles returned to romantic comedies in "The Prince and Me," playing a college student wooed by a member of the Danish royal family masquerading as a student. According to reports, sparks flew with her co-star Luke Mably.

Although Stiles has never spoken publicly about a real-life relationship, she has talked fondly of Mably in several interviews, including complimenting his talents in  chat with Live About. "... 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 while discussing how they developed their chemistry for the film.

However, there was one occasion when Stiles appeared slightly annoyed by the Brit. While promoting the film on a press conference call, she expressed surprise (via The State Times) that Mably had apparently claimed that they didn't rehearse much beforehand. She responded, "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."

After dating a string of actors, Julia Stiles dated an artist in the mid-'00s. The "Save the Last Dance" star had a two-year relationship with Jonathan Cramer, described by New York Magazine as "Think Jackson Pollock, minus the self-destructive alcoholism," for two years.

In 2006, Stiles paid tribute to her then-boyfriend 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.