Almost any of the Steven Starr restaurants are unusual enough that I usually try to take out-of-town guests to at least one while they're in Philly. It's an event, almost as much about the setting as what's on the plate, but I've found the food to be pretty solid at most of them, spectacular at some. Buddakan is the classic Asian-fusion thing, Tangerine is Moroccan-inspired, Pod has good Asian fusion food and the decor is amusing, El Vez is upscale mexican, and Morimoto has really great Japanese (try the omakase if you don't mind spending $80 or more per person!) There are others of course, but those are the ones that have been most impressive to my guests in the past, and have had the most consistently good food. Any of his places are good spots for a (pricey) cocktail, and perhaps an app at the bar. All of those spots are a little dressy, but I've never worn a jacket... I'll second the recommendations for getting a roast pork sandwich, and cruising the Reading Terminal Market, and DiNic's is a good way to do both at the same time. Breakfast or lunch at one of the Amish counters at the Terminal is pretty unique to this area, plain hearty country fare, but fresh and good. A really good Philly hoagie is a wonder to behold, I favor Sarcone's but there are endless disscussions about this in other topics here, and a valuable reference to these types of eats, as mentioned before, at Holly Moore's site The South Philly red-gravy restaurants are a truly authentic Philly thing, but probably not all that exotic if you can get homey Italian where you live. Nonetheless, a simple pasta at Ralph's is pretty satisfying (don't bother with the fancy stuff, just get the gnocchi, or ravioli or something like that.) There's better, fancy Italian if you want it, but the simple places are a more specific Philly thing. Philly has a very solid Chinatown, and Nan Zhou hand-drawn noodles might offer something different than home. Rangoon is really terrific if you don't have Burmese near you. The big Philly trend in the last few years has been the good, small BYOB. If you can get a reservation at Django, do it (and yes, get the cheese plate). If you can bear waiting around on the street, try Melograno. There are lots more mentioned above, I'm sure folks will post more faves. if there's something in particular you were looking for, ask, I'll bet someone here knows where to get it!