Question: movie where a popular guy dates an unpopular girl?
Answer: 2. 10 Things I Hate About You (1999) 10 Things I Hate About You is full of characters trying to change who they are to impress a lady/fella. There's the nerdy guy trying to impress the popular girl, so he pays a rebel to seduce said girl's mean older sister, who used to be popular but now hates everyone.