For my first date in NYC, I would definitely go to a place that I find comfortable and relaxed. My favorite restaurant is Maria's Mont Blanc on 48th. Great food and big martinis. And, I know this sounds cheesy, but if this first date went well, then I can think of nothing I like more than riding around the Circle Line Hudson tours. Being out on the water [and] having a drink under the Brooklyn Bridge can be magical on the right night in NYC. Ah, romance!