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Let’s be honest. If you were a teenager in 1999, two things kept you up at night: Y2K and wondering whether Heath Ledger and Julia Stiles had a real-life romance. Anybody can root for a good celebrity relationship, but there was something special about these two. 

For starters, it’s fair to say we all have a soft spot for 10 Things I Hate About You. The two shared an on-screen chemistry so strong it made us root for them in the movie and in real life.

Beyond their on-screen synergy, this movie showcased two brilliant Hollywood careers in their infancies: A witty, well-spoken young actor born into stardom due to her NYC roots and a young heartthrob Aussie with potential as big as his personality — tragically cut far too short. 

First, the movie that put Ledger and Stiles on the map:  

The staying power of ’10 Things I Hate About You’

10 Things I Hate About You begins when Cameron James (Joseph Gordon-Levitt) asks Bianca Stratford (Larisa Oleynik), sister to Kat Stratford (Stiles), on a date. Informed of the new rule laid out by the Stratford sisters’ father (Larry Miller), he realizes he must find a suitor for Kat if he wants Walter’s blessing to date Bianca. 

Alas, Cameron chooses the quintessential against-the-grain bad boy Patrick Verona (Ledger). With assistance from Michael (David Krumholtz), Patrick finally agrees, only to be met with heavy pushback from Kat. However, after secretly discovering Kat’s passions, the tables turn for Patrick. 

On the other side, Cameron continues to pursue Bianca, who is simultaneously preyed upon by the douchey Joey (Andrew Keegan). They all attend a party where Kat begins to open up to Patrick. They almost kiss until Patrick pulls away, prompting Kat to leave, thoroughly enraged. Cameron’s efforts are failing as Bianca gives Joey her attention. 

However, she soon realizes the true douche that Joey is, asking Cameron for a ride home instead. The two kiss when Cameron admits his feelings for her. 

In a whirlwind of emotions, Patrick is paid by Joey to take Kat to prom so he can ask Cameron. Frustrated that Cameron hasn’t asked her to prom, Bianca agrees to go with Joey. Kat admits to Bianca she slept with Joey during freshman year,  warning her of his advances. 

Bianca reminds Kat that she can make her own decisions but still goes with Cameron instead. Kat agrees to go with Patrick. At the prom, Joey is angered when his plot for prom-night sex is revealed to Bianca. So he reveals his cash proposition with Patrick, crushing Kat and causing her to leave.

Heath Ledger and Julia Stiles film a scene for '10 Things I Hate About You'
10 Things I Hate About You stars Heath Ledger and Julia Stiles | Buena Vista/Getty Images

Joey socks Cameron but instead is beaten up by Bianca for his efforts. Bianca heals Cameron’s wound with a kiss. The next day Kat and Bianca make good again. Bianca begins dating Cameron.

Kat reads her own version of Shakespeare’s Sonnet 141 as part of an assignment, a poem appropriately titled “10 Things I Hate About You,” where she reveals she’s in love with Patrick despite his mistake. Patrick surprises her with a guitar he paid for with money from Joey. He confesses his love for Kat. The two kiss, and all is well. 

The unforgettable chemistry of two young stars

There’s one thing that separates 10 Things I Hate About You from the other Dawson’s Creek-esque cheesy teenage love overtones: the on-screen chemistry of Stiles and Ledger. The two caught fire in this movie – enough to prompt rumors about a real-life romance between the two. 

Many fans believed the two had a secret relationship they hid from the public. The more you watched them in their performance, the more believable the rumors became. However, the film’s director, Gil Junger, quelled the rumors, as referenced in a quote in The Things, claiming he didn’t think the two got together behind the scenes. 

Despite the fact the two were never romantically involved, it never stopped Stiles from reminiscing about her fond memories with the young actor, on and off-screen.

In one of her favorite memories, Stiles recalls a scene where Junger directed Ledger to run up and down the steps while filming his hilarious musical performance in 10 Things I Hate About You. 

She remembers Ledger running so fast the guards couldn’t keep up with him. A nurse had to check one of them out for fears of a heart attack, attempting to keep up with the young actor. With this, we’re warmly reminded of the short but shining career of Ledger and the explosiveness of the two in this memorable movie. 

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