Plans are for the non-creatives. When you live in a city in which you must take the subway everywhere, things can get a little... hectic. Couple that with trying to find dollar bills for ticket fare and no knowing exactly where you're going and you've got yourself an adventure. Sure, it's nice to know where you'll be spending your evening but wouldn't you rather walk through belmont for two hours, completely drunk and unsure of what direction you're headed? Taking pictures with anything and everything, not really sure of when your spinning will come to a stop.
Some nights, it's not the hott hipster destination but the wildly unplanned journey of getting there.