What is the movie where?

Question

the guy is like in love with the girl, and at one point he says something along the lines of "you have 7 different smiles," and he lists them off?

I honestly cannot remember anything other than that.

Answer 1

Win a Date with Tad Hamilton! It starred Kate Bosworth and the guy from that 70's show Topher Grace. He tells her this "Like do you know she has six smiles? One when something really makes her laugh. One when she's making plans. One when she is laughing out of politeness. One when she is uncomfortable. One when she is making fun of herself. And one when... she's talking about her friends."

Answer 2

when a man loves a women Andy Garcia say's it to Meg Ryan