2. Sleepless in Seattle

On the surface, this might not seem like a movie about Valentine's Day, and on the surface, that's true. Don't get me wrong, it's sweet as can be, it epitomizes the idea of what Valentine's Day is supposed to be about. However, it's also a holiday themed movie. After all, the most climactic scene takes place on Valentine's Day. What's more romantic than seeing Sam and Annie finally get together?