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It's a bit touristy, but the Top of the Rock has an amazing observation deck - the view is superb, and the location is better than the empire state bldg. You can reserve a time slot online, so you don't have to wait in the rat maze in the basement of the ESB.
Portofino Grille on First Ave at 63rd St is a great non-touristy Italian restaurant. It's close to where I live, so I go there a lot. Always good - tons of food, and lots of room inside, you won't be packed in like sardines.
Old Homestead Steakhouse - down in the meat packing district. Not as "businessy" as the midtown places, and the food is every bit as good, if not better.
As vip300 mentioned, Dallas BBQ is really good - the 42nd St location can be really crowded, but it is the newest one, so probably best to go to that one. Not expensive and not fancy, but always good and easy on the wallet.
Divine Bar - two locations - East Side and West Side - The food is too fancy for me, but if you like to try different wines, they have hundreds of them by the glass. They have a nitrogen tap system, so they even do expensive wines by the glass. Not a bad beer selection. The Easy Side location does not serve liquor, only the West Side one does.
For a goofy piano bar place, there is Don't Tell Mama - This is a little touristy, but can be fun on a cold night - always busy, but good service from waiters so you don't have to fight the bar. A little ***, but women tend to like this place.
If you are down for one of those all you can eat Brazilian places, try Churruscaria Plataforma. The one in midtown gets packed, so make a reservation. The one in Tribeca is less crowded, and the newer location. You won't leave hungy.
The best dive bar in town is still Smith's on 8th Ave - a bit rough for a lady, perhaps, but fun and not expensive. Reminds you of what the Times Sq area used to be like.
Have fun - and leave your 300 at home - every garage in Manhattan sucks, they all beat up your car.
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