Smoke 'em if you got 'em

If you want to be a better street photographer, start smoking. (I know, I know. Thanks for the paternalism and all, but try to look beyond the surgeon general's warning to the social issues being discussed.)
Waiters in Paris take a smoke break.
Stop at a cross walk. Get on a train. Wait in line. Stand against a wall. What do you hear from the strangers next to you? Silence.

We live in a world filled with fear. Signs warn us that "if you see something, say something!" because every stranger these days is, at best, a terrorist or a serial killer. It's a culture that begets unfriendliness and closes people off to casual discourse. That environment is poison to street photography, and has led to the depressing forms of Weegee-style confrontational work which dominate street photography blogs and Flickr.

What's needed is a return to civilization, where people aren't afraid of their fellow citizen and welcome the opportunity to connect and share. Until some social upheaval brings that about, though, we are left making due with the situation we're in.
Smoking a cigarette in a stairway in Spain.
Great photographs are about an intersection of events in time and space. Sometimes the photographer happens upon a scene already in progress, and the photograph is made quickly because there is nothing missing. More often, however, a photographer recognizes a scene as significant, but it's incomplete. The light needs to be different, the people aren't engaged right, or maybe there's just traffic or a group of pedestrians in the way.  Whatever the impediment, the photographer has to wait for the scene to come together: the point in space is the right one, but the time isn't yet right.

Entering the personal space of strangers is never easy, whether you're starting a conversation or just lingering long enough to wait for a convergence of events to make an image. Standing around looks suspicious, pacing makes a person appear angry, and the contents of that mysterious bag on your hip draws unwelcome attention. (Don't delude yourself that the stealth fanny pack is less provocative. It's probably worse than a giant Lowepro.) Striking up a converation about the weather or street construction with a stranger you want to photograph will likely be interpreted as creepy (and it likely is), but even worse it will bring attention to you when you start taking pictures—and attention to the photographer does not good pictures make.
What you need is a socially acceptable reason to be where you are for a period of time which you can control, and which will not draw adverse attention. Sometimes you can get dismissed as a tourist by taking an occasional picture and acting disgusted about the sun's location. But sometimes it looks like you're casing the place or stalking someone. (Remember: Strangers are terrorists!) It would be better to have something more predictable and subject to public verification so the cops don't need to be involved. It would also be great if that reason were universally useful no matter to what city you travel, or what language you don't speak.

There is such a solution: the humble smoke.

A cigarette is the last social lubricant we have that works worldwide. It works because it's the Swiss Army knife of social interaction. Without words:

  • everyone knows what it is
  • It lasts for six minutes, maximum, but it's acceptable to extend that time with another
  • It must be used outdoors (unless you're in a civilized country that still has indoor smoking)
  • It can be given as a gift, or one can be requested, without awkwardness 
  • A pack of 20 is apparently tied by law to the price of Starbucks coffee, making the investment minimal
  • A pack may be obtained legally anywhere that isn't a strictly Islamic country. (And maybe not in Singapore. I'm not sure about Singapore.)

These facets are extremely useful for the street photographer, and can transform the images you make.

You can loiter

Acceptable loitering is where a cigarette shines. Everyone knows that smoking a cigarette takes time. Specifically, about six minutes. This is often adequate time for a scene to evolve. Moreover, it's a socially acceptable excuse to maintain a fixed location. If you're escaping the afternoon heat, it's also a valid reason to be hidden in the shade. So long as you're smoking a cigarette, the most you'll get is a dismissive glance.
Roma gypsies loitering in Spain.
You can't loiter indefinitely, but smoking two or three cigarettes in a row is not socially unreasonable, and can buy you quite a solid block of time. Playing with the pack, struggling with the matches, fumbling with the lighter—these are all socially acceptable forms of delay.

A cigarette diminishes the perceived importance of what you're doing

People are egotistical and imaginative. When someone sees a photographer taking their picture, they're quick to make all kinds of negative assumptions about for what nefarious purpose the image will be used. Diminishing those concerns is desireable.  If you photograph while holding a lit cigarette, it makes it appear that you're taking pictures to pass the time while you smoke, thus diminishing the importance of the photography itself, thus making it less of a big deal that you're taking pictures in the first place.

You can talk to strangers, and take their picture, too!

Overcoming the modern day resistance to strangers isn't easy. Even where people are sharing a common experience—like a train ride—it's very difficult to start any meaningful dialog, and harder still to maintain it.

A primary reason for the difficulty in having a conversation with a stranger is that we have no cues indicating control because we don't know that person. We don't know whether we will like talking to a stranger, and if we don't like it, we don't know how best to disengage with that person. By default, it's easiest just not to start the whole process.
Smoking at a cafe in Spain.
Our hostile society has created a few conventions to deal with the issue. Speed dating is an example. Bars and clubs have a set of expectational rules. But out on the street the acceptable interactions are extremely brief: friendly greetings, checks on the weather, a reference to a sports team. These may be sufficient to acknowledge another person, but it's rare for those interactions to lead to longer conversations.

Again, the cigarette is the savior. It is like a fuse of a known quantity: you start the interaction with a light, and you know you don't have to invest more than six minutes. Because there's a clear end at which it's socially acceptable to move along, the cigarette invites more open conversation while it's burning.

Moreover, nothing puts a person in a positive mood quite as well as a gift with no strings attached. A level of connection is immediately achieved by offering or accepting a cigarette or a light, breaking the ice early.
An estate manager in Spain, who bonded with the photographer over a smoke.
There's also connection with a fellow smoker because you're both already pariahs. Being an outcast is tough to endure. It's a lonely existence, and misery loves company.

Smokers also make great subjects. They tend to be doing something while smoking, so they're often animated and engaged.

Even if the stranger isn't a smoker, there's a high chance the non-smoker will be sympathetic with your perceived addiction (we all have our addictions, after all, and no one wants to start a pattern of judgment) and try to make you feel accepted. Sympathy often leads to dismissal, and being ignored is a street photographer's best friend.
A woman throughly enjoys her cigarette at a cafe during a warm Parisian night.
Finally, as you struggle with your impending decision to light up, consider the history and utility of smoking in the creation of great photography. The Hungarian street photographer Brassaï, whose 1933 collection Paris de Nuit should be in your personal library, photographed Paris only after the sun went down. Brassaï used a cigarette to time his exposures: "To gauge my shutter time, I would smoke cigarettes—a Gauloise for a certain light, a Boyard if it was darker."

So as you can now appreciate, cigarettes are a street photographer's secret solution. Get smoking.