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For something "different" try Root. Really good food coming out of their kitchen and it will definitely be a "fun" dining experience.
I would suggest that a person who doesn't know which kinda upscale place he wants to visit in NOLA might want to stay a little more traditional than ROOT. It's not an entry level semi-fine dining establishment.
I'd suggest one of the old line classics from Commanders to Galatoires or the have to go at least once places or one of the newer NOLA classics like August or even the new Rest Revolution. If he's not wanting to drop $500 for 2 people then maybe Lilette uptown or anything else that doesn't serve smoking cigar boxes of food.
Or, if that's what he wants, then do Stella instead of Root.