No matter how great a Time Out NYer you are, the best of venues can turn duddly, quickly.
Be the man with the plan. Before enjoying a night out, note a few places in the area, including accessible rooftops. With a simple Google search, you can point your eager troupe in a new direction; surprise them with a back alley burlesque show, a speakeasy of old.
On the other hand, a blind adventure makes for a great evening too. Planning nothing at all can be the best plan. All you need is an open mind and the desire to try anything.
The best night of my summer was an unplanned excursion to South Street Seaport, ending on a sailboat filled with handfulls of nubile college women. No planning involved.