How about going on the ferry (in NYC)it can be interesting out on the deck weather permitting, free and you can have an interesting conversation about future plans such as where you would like to live, how many children and what occupation you plan to go into.
While going out to eat is enjoyable, many girls are uncomfortable eating on a date either because they are weight conscious or scared they spill something one their new dress. Add to that kashurus problems and that she may orders the most expensive item on the menu, I think you should find a different venue for the date.