Many men struggle with thoughts like: "Where should I take her?" or "What should we do?" Some men try to shock-and-awe with an over-the-top plan (which can come across as overwhelming, or even weird), while others come with no plan at all (which clearly communicates a lack of planning and/or caring about the date). 

What she wants: Something casual, fun, and interesting, with no pressure from him or for her. It should spark conversation (so going to the movies should be out) and reflect some thought into the man he is.