Gramercy Tavern is probably NYC's fave restaurant. The building itself is a landmark, the interior is homey yet elegant, and the food has been consistently ranked as the best of the best. It's too upscale for just an ordinary date night, and with its warm ambiance and candlelit decor he'll be in the ideal place to pop the question. Bonus points if he snags a key to Gramercy Park and brings you there to propose after dinner.