Grand Central is an incredible place, even if you're not taking a train. Amazing architecture, some nice little bars and all the people watching you could want.

Actually, people watching is a helluva way to spend some time in NY. Find a sidewalk cafe in Greenwich Village. You're guaranteed to see some interesting folks.

Other people have mentioned Central Park - it really is beautiful. I remember seeing horsedrawn carriages near the park as well.

Some good suggestions here. Also:

MOMA and walk along 5th ave up to Central Park
The Standard Hotel Beer Garden and the Meatpacking
Frying Pan and walk along the Hudson River Park
Bowery Museum, the Lower East Side, and Nolita (near Katz's)
have a drink at the Pourhouse (3rd ave and 11th st) the KU bar

if you get lucky get her to stay the night with you and then the next day try:

The Bronx Botanical Garden
Grants Tomb
Columbia Campus
The Cloisters

One other thing about New York - the street numbers are odd. In Chicago, each block starts a new 100 for addresses, so, for example, you know if you're in front of 200 West Madison, 300 West Madison is a block away. NEW YORK IS NOT LIKE THIS. I remember walking up one of the main north/south streets, thinking I was a block away from my destination when in reality I was about six blocks away from my destination. Also, in the Midtown area, the blocks on the east/west streets are about three blocks long. That can throw you off a bit.

And lastly, it would probably be prudent not to stray north of Central Park.

I loved seeing the top of the Roc, and empire state building. Also, have to recommend broadway. I took my family to see greese on broadway, and everyone loved it! Chicks really dig it though, so makes for a good date. Hope you have fun.

This is incredibly cool. The horsedrawn carriages are much better than the guy pulling you on a bike. very awesome.

Yes if you do the "go to the top of a building thing"... got to Rock Center, not the Empire State Bulding

Make sure you get some great NY pizza.

http://www.stopmikelupica.com/images/Sbarro.jpg

:D

we saw The Lion King on broadway. WOW what an experience.

Oh, and you have to also go to the legendary Mcsorleys. ;)

http://www.mcsorleysnewyork.com/

I took a friend there and he asked ''what kind of beer do you have'' and the Irish dude goes ''Light and dark''

ROFL

I think he wanted a coors lite or some shit..the servers there carry like 50 mugs at a time bringing beer to tables..they are soaking wet with beer.

For a drink in a nice, but not too overdone, place, have the famous Red Snapper (Bloody Mary) at St. Regis Hotel. They claim they invented the cocktail.

Walk around TriBeCa and look for Robert De Niro. Maybe he's in his restaurants.

Go to Chinatown and buy your lady a nice $7 gold watch. To show her you really care, bargain. But be polite about it.

Look for the statue of V.I. Lenin peering over to Wall Street.

Go up and down the blocks near the main library (42nd st?) and read the little squares on the sidewalk.

Go to the MET. It's free. You can walk around the place where they collect money.