Of course, I've had some large bills picking up a tab at a larger party, but the most expensive single meal I've ever had was at Charleston in Baltimore. I don't recall the exact amount in the end - It was something north of $500 for two, and with tip was therefore well over $600. I do remember cringing at the tip being into three figures. I enjoyed the meal, I'm glad I did it, but I can't imagine ever eating there again. It's simply not affordable, and really I'm not sure any meal short of some kind of "destination" place like El Bulli (sadly, despite several applications, never to be) or TFL is worth that kind of money. I like to eat, but it's extravagant to a point I'm not really comfortable going.