Within a big city, it seems as though it should be possible to satisfy the interests of most people on a regular basis. Those who like art, music, or theatre should be able to find things to their liking often. Likewise, parties, clubs, bars, museums, and the like should be accessible. Clearly, those with exotic tastes will have a tougher time than those with mainstream ones, but it seems as though big cities should cater to most plausible sets of preferences.
When a person lives in a city and has done so for a while, this is usually true. The difficulty arises when one lacks access to local knowledge and people. Then, one becomes a kind of urban refugee: moving between public spaces like coffee shops and tourist spaces like ordinary museum exhibits. It can be quite frustrating to be in an amazing place like New York, London, or Montreal, certain that there are interesting things going on, but being unable to track something down.
How does one go about making the transition from the former to the latter – from engaging with a city like a tourist does to doing so like a local version of yourself would? I am thinking mostly about cities where you speak the language, but advice for situations where there is a further linguistic challenge would also be appreciated.
The obvious answer is to find a local who will show you around.
In the alternative, act much more extroverted than you normally would. You will creep some people out, but you might find some good opportunities.
Locally produced blogs and new media will fill part of that gap, especially regarding cultural events. Of course, one does have to figure out which are the best sources for that information but generally people will be happy to tell (eg. that they use the Georgia Straight, or the little Guardian supplement on Fridays). Finding an arts cinema and/or good local record shop might help because it gives you a little access into the artsy subculture; at worst you see cool old movies & listen to music. Speaking of which, I heartily recommend The Battleship Potemkin (regularly listed as one of the C20th best 100 films, despite being both silent and in black and white because the images are spectacular).