do you like tasting menus??
do you enjoy three hour long meals served over five to nine courses??
do you want to sit in a relatively quiet and somewhat boring room, surrounded by a mostly older (generally late 40's and way up) kind of crowd??
do you really want to spend $300 on a meal like this??
or more appropriately, does she??
if so, then go ahead.. and yes, you should wear a jacket to the rear room at gramercy tavern..
if not, and if you're not looking to propose, you might want to look into a place with a better vibe..
some people like WD-50, some don't..
L'Imperio for a multi-course dinner, with a good price, and a nice vibe, in a great little neighborhood that she's probably never been to..
Le Bilboquet if you need to French it up, at least it's authentic in it's being old and odd..
either room at the Modern, next door to the MoMa, while no less expensive than a meal at Gramercy Tavern, will provide much better and more interesting food, in a younger and more festive feeling room..
Blue Hill is special, and will create a tasting menu and can pair wines, etc. at your request, with a more seasonal take on things.. smaller dining room, near Washington Square..
Cafe Grey before it closes..
Perry Street..
All are at least somewhat less typical and most have better food and atmosphere.. in my opinion..