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Julia Stiles is like a bad-ass cherub. Intelligent, bold, classically beautiful and the star of our favorite 2000s rom coms alongside the most swoon-worthy guys—Freddie Prinze Jr., the late Heath Ledger, Sean Patrick Thomas.
Yet somehow, while she sashayed and angst-ed her way through high school as the object of affection for only the finest of fine men, we couldn’t be jealous; we always rooted for her and never, ever hate her, not even a little bit, not even at all.
So, in light of the fact that news broke today the 36-year-old star is pregnant with fiancé Preston J. Cook, it seems only right to celebrate her impending motherhood with a brief romp through her sweetest romantic comedies. Because these cinematic showcases of heart-tugging performances feature signature, nuanced Stiles-ian authenticity and are still just as good as they were years ago. 

10 Things I Hate About You

Year Released: 1999
Starring: Julia Stiles, Health Ledger, Joseph Gordon-Levitt and Larisa Oleynik
Standout Stiles Moment:

Save the Last Dance

Year Released: 2001
Starring: Julia Stiles, Sean Patrick Thomas, Kerry Washington and Fredro Starr
Standout Stiles Moment:

Down to You

Year Released: 2000
Starring: Freddie Prinze Jr., Julia Stiles, Ashton Kutcher and Selma Blair
Standout Stiles Moment:

The Prince & Me

Year Released: 2004
Starring: Julia Stiles, Luke Mably, Miranda Richardson and Ben Miller
Standout Stiles Moment:

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