Don't forget times square. Sometimes (not lately), I'll just walk up there late at night and chill. It's sort of inspiring in a weird way? Just sort of shows you the size, and power that NYC holds
did you want to do a lot of shopping? There's tons of places for everything you want. Definately make it down to Soho. the Bapes store is down there. Expensive, but sick place to get some new gear. Also theres tonnes of places for your girl to shop. All kinds of boutiques. If you really wanna break the bank, just hit up 5th ave in midtown. Your girl can convince you to buy her a $250 burberry scarf, or some other stupid shit. Definately hit up Canal street to get some cool shit. Cologne is cheap as fuck. lso if you wanna get some fake watches and shit, that's the spot. You girl can get her fake bags too if 5th ave is too expensive.
Definately check the Statue of Liberty/Battery City Park. Go to Central Park, etc. Actually theres a GREAT book that I got when I first visited and moved here. It's called "New York City - The rough Guide" and is authored by Martin Dunford and Jack Holland. this book SAVED ME!! It's got all the maps, and different sites, facts, etc etc about EVERYTHING in the city, and its easy to follow. It's got every district in a different section so each spot you go, you can see everything of importance in that area. The ISBN # is 1-85828-507-0. Seriously, I promise this will make your trip a whole lot easier, and you wont look like a big nerd/tourist walking around with a city map (which in turn may possibly save you from being pickpocketed lol)
Have fun while you're here!