The Truth About Julia Stiles' Dating History

Julia Stiles has been in the spotlight for most of her life, having launched her acting career at the ripe age of 11 with her debut at the La MaMa Theatre Company in New York (via The Famous People). After appearing in several stage productions, she landed roles in teen films "10 Things I Hate About You" and "Save the Last Dance." Her career has been going strong ever since, with parts in movies including "Hustlers," "Silver Linings Playbook," and the Jason Bourne series, as well as television shows such as "Dexter" and "Riviera," per IMDb.

While Stiles has become a fixture in Hollywood, she's kept her personal life under the radar. She did, however, share with Cosmopolitan in 2001 just what she was looking for in a guy: "He definitely has to be open-minded and have a sense of humor — I want to have fun with the guy I'm with," she said. "But of course, sexual attraction is really important — without that, you'd just be friends. I think Latin guys are really sexy. They generally fit into that whole tall, dark, and handsome thing."

Which guys have fit the bill for the talented actress? Here are a few of her more well-known love interests. 

While fans of "10 Things I Hate About You" were blown away by the chemistry between on-screen love interests Julia Stiles and Heath Ledger, it turns out the actress was fixated on another co-star during the shoot: Joseph Gordon-Levitt. In fact, during the movie's pivotal scene where Stiles' character reads a poem about her unrequited love, she was thinking about her feelings for Gordon-Levitt.

"They were very, very attracted to each other," the film's director, Gil Junger, revealed to Nylon. "She's professing her love to [on-screen boyfriend Ledger] and she's in love with a guy waiting in his trailer to shoot the next scene." He added that the two dated "for a minute or 10," stating that "it was beautiful how much they enjoyed each other."

Neither Stiles nor Gordon-Levitt has ever confirmed or denied that they were once an item, but Stiles looks back fondly on the shoot. "I have so many great memories from that movie that are fading, because it has been 20 years," she told Us Weekly. "But it was just such a special time where we were all so excited."

Julia Stiles moved on with Josh Harnett, who starred alongside her in the 2001 film "O." Hartnett — who has also been in relationships with former co-stars Scarlett Johansson and Kirsten Dunst — is fine with dating his co-workers. "I think it's a respectable way of going about it," he told Playboy (via Us Weekly). "I've met very important people in my life doing films. Sometimes that had consequences that were just awful for everybody involved. Some were fantastic all the way through. Everybody makes mistakes dating people they work with."

After things fizzled out with Hartnett, Stiles reportedly hooked up with her "The Prince and Me" co-star Luke Mably in 2004. Stiles has revealed, though, that the two didn't have instant on-screen chemistry. "But 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 told Live About. "So, in that sense, we didn't have good chemistry. But I feel like that's part of my work as an actor, to be able to use my imagination and not be so dependent on how I'm relating to my co-stars."

After her two-year relationship with artist Jonathan Cramer ended, Julia Stiles landed a role in the Showtime series "Dexter" playing the love interest of the main character, who is portrayed by Michael C. Hall. Sources claimed that "'their chemistry was so crazy and so evident to everyone that writer and producers, seeing it play out on set, actually cranked up their sex scenes to capture it for show" (via Daily Mail).

Rumors soon began circulating that the two were coupling up off screen as well. There was just one problem: Hall was married to Jennifer Carpenter, who played his sister on the show. The two soon announced they were divorcing, and Stiles denied she had anything to do with the demise of the marriage.

"I have absolutely nothing to do with the split between Michael and Jennifer. We are good friends and enjoyed working together," she told Us Weekly in a statement. "This is a personal matter between them, and we should respect their privacy. Although I too prefer to keep my private life private, I felt compelled to dispel the rumors I was somehow the cause for this matter."

Before he became a household name due to his work in "Stranger Things" and "Black Widow," David Harbour was best-known as Julia Stiles' plus-one for four years (per Elle). The couple even worked together on the 2013 movie "Between Us," which follows the rocky relationships of two different couples. "That subject matter is my jam," Stiles told Pop Entertainment. "Meaning I can't get enough of stories that explore the nature of love, marriage, fidelity and commitment."

While Stiles and Harbour were often seen together in New York — and even walked the red carpet with one another on several occasions — their relationship stayed mostly out of the spotlight. The two eventually parted ways and Harbour has since moved on, marrying singer Lily Allen in 2020. "I married a beautiful, incredible woman who I love," he told People. "I have never met someone who is so deeply kind as her. I've never felt so taken care of and cared for by another human being."

After dating a bevy of actors throughout the years, Julia Stiles finally found true love — with someone working behind the camera, no less. She met Preston Cook on the 2015 film "Go With Me," and they got engaged that year on Christmas Eve. "We went on a big trip with his entire family over Christmas and New Year's," Stiles revealed on "Today" (per Bustle). "So I kept saying to myself out loud, like every day, 'Do not ruin a perfectly good vacation by getting your hopes up. Just get it out of your head.'"

The couple continued to work together on a "Jason Bourne" film as well as on the series "Riviera." They married in September 2017 and welcomed their son — Strummer Newcomb — one month later. Stiles celebrated their three-year wedding anniversary by posting a wedding photo on Instagram with the caption, "Three years, Five countries, Two Quarantines, and we haven't killed each other. Happy Anniversary, Luv."