10 Things I Hate About You (1999)

Directed by Gil Junger and inspired by William Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You stars Julia Stiles and Heath Ledger as two strong-willed teenagers drawn into a complicated high-school romance. Joseph Gordon-Levitt and Larisa Oleynik co-star in this late-1990s romantic comedy built around dating schemes, rivalries and shifting relationships.

Från IMDB:
A high-school boy, Cameron, cannot date Bianca until her anti-social older sister, Kat, has a boyfriend. So, Cameron pays a mysterious boy, Patrick, to charm Kat.