Interesting article in the Times this morning discussing both the ways different restaurants seek to appeal to men and/or women and how men and women are sometimes treated differently in restaurants.
To get the conversation started, I've ordered for women before and been the "dude" on occasion, typically with women my own age (I'm in my mid twenties), younger or much older. I learned pretty quickly that women in their 30's and 40's don't appreciate this much. It seems like something of a mindfield navigating amongst the confluence of etiquette, some benign and cute, if anachronistic, patriarchy, and some wounded pride across the table. I pity the server having to do that more or less blindly.