Sometimes the stochastic flow of people mingling on the sidewalks makes it more challenging to make that structured attack, and successfully trap the right someone in front of the lens, so I propose a more daring, aggressive and potentially less ethical approach in order to chase down those who catch your eye. Stalking is a strong word, which I use hesitantly, but then again probably best describes the aggressive 'get in-front of my camera' last ditch effort.
Imagine you have been wandering the streets all afternoon long with nothing to show for it, except aching feet and a mild case of heat stroke, when suddenly out of the corner of your eye you spot a man dressed to impress, all power marching down the opposite side of the street. These are rare opportunities for those of us living in sparsely populated cities (we do not have the density of New York....), but with a little game of cat and mouse you might still have a chance to get your shot.
I am not suggesting you make a mad dash across the street chasing down your subject, waving your camera in the air yelling 'wait! wait! wait I want a picture!'. A little more subtlety will pay its dividends if you wait for the opportunity to ripen, so hasten your pace and engage the pursuit. Sometimes it takes a few blocks, street crossings and ducking into shops before you can get within a reasonable working distance to make use of the 35mm lens strapped to your camera.
This is when all the hard hours slaving on the treadmill pay off, a little endurance and fitness will stop you keeling over out of breath, panting like a maniac at the conclusion of the chase so you can deliver your one shot pickup line which gets you the image.
Exercising a little patience is everything in this delicate game of cat and mouse, if your presence gets detected, your chances of getting approval for the shot go straight out the window. No matter how good your pick up lines might be, no one likes a stalking paparazzi, you have been warned! Practice makes perfect but dressing subtly, camera drawn at your side and casually looking around like a clueless tourist helps you go unnoticed.
The real trick is figuring out when to approach the subject, this mostly comes down to personal taste, I make my choice based on the background interaction with the lighting on the day. Therefore catching up with your subject matter is only the beginning, and now your creative choices come into play.
(in-case you missed the earlier post on how to casually approach street portraiture you are welcome to go back and look at the previous post, linked below),