One other cool but likely completely irrelevant idea. A couple weeks ago my buddy read about a place in Coney Island (read: FAR) called
Sahara and decided we were going. So three of us head out there around 7:30 on a Friday night. It's a really cool Turkish (I think) place. It's got all kinds of really tasty roasted meats (chicken, beef, lamb, etc.). It works really well as a family style place; two entres would probably do three people very nicely.
We had a bunch of some Turkish beer (called Efez I think) at diner and didn't really know what to do when we left. We saw a liquor store just down the block and each picked up a bottle of champagne to drink while we walked around. This neighborhood was completely empty, I wouldn't advise walking around Manhattan gulping champagne out of the bottle.
Eventually we saw a sign for the Beach and decided to go check that out. It ended up being kind of a hike but it was a lot of fun being basically lost in what feels like a completely different city from your own, all the while getting wasted. We walked around the boardwalk for a a bit and talked to some random crazy guy that was also on the beach.
On the way to the beach we had passed a club called
Rasputin. There were no reviews for it on Yelp and they both describe it as a caterer/restaurant. I'm pretty sure the address is right but it definitely isn't a restaurant. There were hot chicks and a red carpet outside...IN THE MIDDLE OF BUMBLE****, BROOKLYN!We had to check it out. What it turned out to be was a dance club full of the most beautiful Russian women I've ever seen. I usually am not that into Eastern European chicks but these girls were drop dead gorgeous and the girl/guy ratio was probably 2 or 3. That being said, we were the only people there that weren't obviously Russian. We walked around getting shot down by lots of chicks and then snuck into the second floor VIP area to hang out for a little while. It was an awesome time.
Anyway, the point, I guess, is that one of the most fun things to do in NYC is basically get lost and not really know where the hell you're going to end up. There's tons of cool/crazy stuff/people here and you're going to run into some of them no matter what you do.