Down to You (2000)

College coeds in New York City, Al (Freddie Prinze Jr.), the son of a celebrity chef (Henry Winkler), and Imogen (Julia Stiles), a talented artist, become smitten the second they lay eyes on one another at a bar. However, the road to happiness is not a smooth one. Outside forces, including a predatory porn star (Selma Blair) who wants to lure Al into her bed, threaten to pull apart the young lovers before their romance has a chance to really flourish.