Dont go to the pokemon center, its huge fucking ripoff.
Well lets see, you can go over to Rockefella center and watch them get the tree ready, they light it in a few weeks.
Or you can go see Blue Man Group down at the Astor Theater.
I suggest going and buying a bag of Country Cheddar Popcorn from Popcorn Indiana. I think its on 48th and Bway or 48 & 7th, not sure. You cant miss it, its right on the corner.
In terms of getting around the city, you might be better off getting a metrocard and taking the subway. Hell if there is one thing you dont want to deal with its the smelly dirty insane cabbies of NYC, that and NYC traffic. Times Square is a virtual parking lot, especially on weekends. You are better off getting a streetwise map of NYC with all the subway stops, and a Metrocard, and just use the Subway to get around.
If you and your friends want to get some drinks, you can head down to Jekyll & Hydes in the Village. Dont go to the restaurant up in the 50's, because its a tourist trap.
Aside from that, most things at night in the city revolve around clubs or bars. I mean if you can get tix to a Bway play, I heard Ave. Q (Sesame St. on crack) was good. If you could get tickets to The Producers, I highly recommend that, because that was one funny ass play.
If you want some good steaks, hit up Sparks Steak House or Mortons.
If you are into anything Japanese, you can visit Kiokuniya bookshop in Rockefella Center.
I know you wont be free until after 5pm, and I dont know what time he closes, but you can go get soup from the Soup Nazi on 55th and 8th Ave.
Hmmmm, there is always the museum of Natural History or the Planetarium.
MoMA (Museum of Modern Art) just reopened, and its awesome.
I would say hit up Central Park, but not after dark.
I guess thats about it. Good Luck!!!!