Not a totally uncommon question, but I have some specific criteria that sometimes is tough to judge from quick descriptions or even websites.
I collected a bunch of money to send our secretary, for her 15th anniversary, to somewhere nice for dinner in NY. I now have the responsibility of choosing where to spend the money. She has never been to NY and lives a very modest life. I want to pick somewhere fancy that she will understand as quintessentially NY. I'm looking for a place with entrees in the mid-to high twenties, to thirties range. I would prefer a-la-carte because she tends not to eat too much, will probably be overwhelmed by a tasting menu, and is going with a few friends so they'll probably want to share stuff, etc. I got a few recommendations from a foodie friend -- he suggested Craft, Gotham Bar & Grill, Aureole, and a few others that are past the price range. Craft looks like it's getting mixed reviews, Gotham Bar & Grill looks good, Aureole seems to offer only a fixed 3-course option. Is there anything else anyone would recommend over Gotham, for my criteria? Also, I don't want any place that is overly pretentious and will make her feel uncomfortable. I was originally thinking Union Square Cafe, but my foodie friend negged it. I lived in NY one summer years ago so I'm totally out of touch with the current dining scene. Any guidance much appreciated. Another friend recommended Blue Hill, but I remember going a few years back and have a recollection that it is maybe too casual for the occasion? No sushi or steak.