What Was Julia Stiles & Heath Ledger's Real Life Relationship Like?

Heath Ledger's tragic and untimely death at 28 years old in 2008 left a profound impact, but fans and costars alike are determined to keep his legacy alive. Nearly thirty years after "10 Things I Hate About You" released in 1999, Ledger's leading lady, Julia Stiles, only had good things to say about the actor.

During a January 2025 interview with E! News, Stiles remembered the kindness Ledger extended when she was just a budding actor. "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. And he was very generous that way." She went on to express that all of the up-and-coming stars in the film formed a tight bond, though Ledger stood out. "He was such a bright light," she remembered, later adding, "He just walked into the room and lit it up." That would ultimately lead to him becoming a Hollywood legend.

During an interview with The Herald Sun (per Elle), the "Silver Linings Playbook" actor recalled what it was like working with the whole cast. "It was a really special time," Stiles said. She raved about Ledger in that interview as well, telling the outlet, "Really interesting, remarkable person and actor." 

The palpable chemistry between Julia Stiles and Heath Ledger throughout "10 Things I Hate About You" left fans wondering if he truly couldn't take his eyes off of her. In other words, there's no way they were just acting during that paintball scene, right?

Wrong. They were reportedly never romantically intertwined. As it turns out, Stiles reportedly had her sights on a different co-star at the time. The film's director, Gil Junger, did an interview on the Spanish web series "Mirá a Quién Encontré" (or "Look Who I Found") in 2021 and detailed the nitty-gritty of the behind-the-scenes romance. "She, for a minute or 10, went out with Joseph Gordon-Levitt," Junger said. "They were very, very attracted to each other, yeah, which was cool."

Remember that infamous scene towards the end of the film when Kat is reading the titular poem out loud in the class? We can't make it through without a dry eye, and neither could the director. Stiles confided in Junger where she drew that raw, unbridled emotion from. "It just killed me," Junger said on "Look Who I Found." "It was so raw, and it was so honest, and it was so vulnerable. Yeah, I even asked her — I said, 'Where did that come from?' And she told me, 'I was just thinking about' — that person's name that she was deeply in love with at the time." Stiles possibly could've been referring to Gordon-Levitt. The rumored relationship was short lived, but it makes us wonder what could have been.