Street Photography: When To ‘Ask’ and When To Snap
Often a candid approach works best, but sometimes gaining permission first has its advantages

I already know what some of the more experienced street shooters are thinking after reading the title: If you have to ask, it’s not street photography. And I agree.
When I shoot a photo that I’ve asked for, I’m careful to label it as a “street portrait”, which in my mind is taking a quick (posed) portrait of a stranger on the streets. (There are also candid street portraits, which singles out an unknowing subject. The terms often get used interchangeably.)
A posed street portrait is not street photography in its purest form, but there are some instances when you can switch between the two disciplines when you’re out shooting. So for this article, I will put all of it under the “street photography” umbrella.
If you’re fairly new to street shooting and want to know when to engage the subject and when to just fire away, then this might be helpful. Here are some examples of my own to explain why I decided to ask, or to just go for it.
The Couple On The Hill
I shot this in Toronto, on a grassy spot in a park that no longer exists (it has since been redesigned). I was meeting a friend downtown and had my camera in hand, as is pretty much the norm for me.
I saw these two nuzzling each other from a distance, but I didn’t have a zoom lens. I tried to snap a couple, but it was uncharacteristically quiet on the streets — meaning I didn’t blend in as much as I usually do. They could see me seeing them. That’s fine, but I wanted their pure connection to come through in my photo.
After positioning myself directly across the street from them, it became apparent that they were being distracted by me hovering. But I didn’t want to walk away without getting the shot. So I took a deep breath and calmly sauntered over to them, explaining that they are a great sight and can I please take their picture.
After some brief conversation and a bit more flattery, I convinced them to carry on as if I wasn’t there while still nuzzling. It’s a bit apparent in the photo that my presence was known (that’s even my business card on the ground in front of his boot), but I think I still managed to squeeze some purity out of this one.
(There are other examples of couples exchanging affection in public that don’t give you much time to react, so you have to shoot fast–such as in the sample above.)

The Traveling Musician
I shot this in Hamilton, Ontario. I was on my way home from a long, fruitless walk — I didn’t have the shot. (I try to get at least one shot I’m really happy with each time I venture out, which is admittedly not as often as before.)
Anyways, I was getting closer to my neighborhood when I saw this wonderful woman — I was immediately struck by her style, and the guitar strung over her shoulder. However, there was no one else around, so I had two choices: point the camera at her, snap, and continue walking — or stop and engage. I chose the latter.
She indicated she was in a bit of a hurry, as she was traveling out of town. Anyways, she afforded me a few shots and I’m so happy with what I got compared to what I might’ve captured had I not asked first. It remains one of my favorite street portraits.

The Chance Encounter
I also shot this one in Hamilton, Ontario. Darth Vader was walking around the neighborhood (I believe to promote a local costume shot.) I saw him coming from the other side of the street, and he noticed me and did the whole I’m using the force on you pose. I got that photo, and it was good.
However, I waited in the same spot after I shot the “posed” photo. I wanted to see how people walking by would interact with him, or if they’d just walk on like nothing was different. I saw the girl coming towards him and waited till they were close, and snapped this as she broke into a little smirk — which could have been from seeing Vader, or also because she knew I was waiting with my camera.

The Fan
Shooting bands at festivals is one of my favorite things to do. Not only are musicians on stage often passionate and photogenic, but you also get a chance to hear their music and even give them a bit of promotion by sharing a photo from their set.
At this festival (in Hamilton), this particular fan was going for it. Dance like nobody’s watching kind of going-for-it. So I got in behind him and waited for him to throw out some more moves, and bang! Asking him to pose or dance for me in this instance would have been counterproductive in my opinion — I wanted to capture his raw reaction to the music.

Image is Everything
This one was shot in Toronto, on Yonge Street I believe. Anyhow, I was pointing my camera into the crowds to single out faces as an experiment, without much luck. Then I saw this Alpha Romeo roll past me and I snapped quickly.
I didn’t notice until afterward how she was checking herself in the side mirror. I only wish she was in a bit better light, but this is one of those times I’m glad I pulled the trigger when I did. (And it highlights that sometimes you don’t realize you have a “gem” until you look through your photos later.)

Eclipse Observer
The solar eclipse of 2017 was a big spectacle — but only if you had the right spectacles as to not destroy your eyesight in the process. I started the day not sure what to shoot — I tried shooting the eclipse through a pair of sunglasses using my live viewfinder, but I wasn’t thrilled with the results.
So I turned my attention instead to people looking at the eclipse, which I found much more interesting. I came across this fellow in a park, and we chatted a little bit — he even gave me an official pair of sky-watching glasses. I told him I wanted something to show how fascinated people were by the sky that day, so he let me snap a few photos. I deliberately underexposed the image so the light on the glasses (which was intense) would take center stage. I could have shot this candidly, but I like how close up I was able to get and how relaxed he was.

Happy Coincidence
One of the advantages of shooting candid is that you’ll get stuff you normally would never even think of asking people to pose for. Such is the case with this image. I liked the composition of the woman on the bench with the woman sitting (sipping water) on the light pedestal.
As I lifted my camera to my eye, the woman furthest from me reached around to pick up her bottle, which hid her head. It created some symmetry and continuity in the picture that I wouldn’t have otherwise captured.

Anticipation
Street photography (as opposed to street portraits) is often about guessing what will happen next and already being ready for it. Kind of like that overused quote from Wayne Gretzky: “Skate to where the puck is going, not where it has been.”
I’m not in any way comparing myself to Gretzky. But the principles are similar for street shooting, as was the case with this photo. I saw the girl running from a distance and the guy waiting for her. I stopped in my tracks and waited, focusing on him, and boom! She leaped into his arms and I snapped this. I had no choice but to shoot, as the decisive moment lasted only a second or two.

Using Humans For Context
Sometimes, I look for scenes that scream out just shoot! Such is the case with this photo, which I framed up in a local park. I noticed the perspective created by the hill and the buildings in the background, and waited for a human subject to wander into it for scale. (I got lucky with the addition of the pup.)
There are many other examples like this where the face of the person or what they’re doing is not important to the overall photo. Instead, you can use people to simply add a human element to a scene (in the form of a silhouette or otherwise) for context.

Candid Snap Or Posed Street Portrait?
It all depends on what you want to achieve, and what you’re comfortable with. Some photographers are perfectly okay with approaching subjects to ask for photos, and that’s fine — when you’ve gained permission, sometimes people open up and give you great expressions. When you shoot candidly, however, you can capture scenes that you would probably never dream of.
You can judge for yourself what might work better depending on the situation. I find that shooting in bigger cities allows for more opportunities for good candids, as you can blend in more. But as soon as people notice my camera, even if I’m not pointing it right at them, I notice that their demeanor changes — and the “purity” is sometimes lost.
You can get great results from both approaches — so don’t be afraid to ask people if you’re not sure! The worst they can do is say no.
When To Think Twice About Snapping
There are some instances where you should consider holding back from shooting altogether. One of them is when shooting the homeless or other vulnerable people (which I get more into here). Also, some indigenous rituals and ceremonies (such as a powwow) do not allow photography in many cases, and that should be respected in my opinion — even if it’s being held in a public space. The best thing to do in some cases is to gain permission ahead of time, and then shoot away freely.
The street is a huge playground for photographers, but using common sense and deciding how to best capture an image (whether asking or shooting away) is important. Deciding on your approach is something that can develop over time. Trust your gut, be careful, try to smile, and most importantly — have fun!
