5 Street Portrait Tips to Overcome Your Fear of Approaching Strangers

It can be scary to start taking street portraits, especially if you’re an introvert. You like being quiet, people are busy and you don’t want to bother anyone.

Photo by KnikmanAV - Hans Knikman
Photo by KnikmanAV – Hans Knikman

But you’re a photographer, so you see all of these “decisive moments,” and every time they slip away, it hurts a little.

Photo by Giuseppe Milo
Photo by Giuseppe Milo

With practice and a few tips, though, you can shoot the photographs you see in your mind. Not to mention, experience the joy of meeting and connecting with diverse people.

Beware, though, before you read on. Photographing people on the street is addicting, and I have a confession. My name’s Benjamin, and, for awhile, I was a street portrait addict.)

I grew up quiet and shy, but I’ve always loved people and would notice the everyday moments on the street. Maybe the shadows on the skin of an old shop clerk. The way a woman’s dress contrasts with the paint on a wall. Or the bright smile of a happy kid.

Photo by Benjamin Jenks
Photo by Benjamin Jenks

Often, I’d let these moments slide past, always kicking myself and feeling regretful. Then one day, I was inspired to face my fears and take self-portraits with as many people as I could.

I was traveling at the time, meeting people, and I wanted to remember them. So why not take it to the next level? I set a goal to shoot 1000 people and then traveled across the USA. In each city and town, I’d walk the streets, asking people if they wanted to take a photo.

Sure, I looked like a big dork (check the photo above), but three months later, I had over 3000 photos with 930 people. Not to mention, I’d learned a lot about how to talk to strangers. Although the fear was still there, now I was in control.

You can do the same.

Street portraits can also promote your photography business, jump-start your career and be a lot of fun. If you’re ready to hit the streets, here are five street portrait tips to get you started on the most challenging part…approaching strangers.

1. Start a Passion Project

Photo by Martin Hricko
Photo by Martin Hricko

Before you hit the streets, start your own photography project. I’m not the only one who needed motivation. Brandon Stanton from the Humans of New York (HONY) also describes himself as “really introverted,” but since 2010, he’s taken over 5000 photos with strangers in NYC. He’s not done either, as his goal is to shoot 10,000 people around the city.

HONY has been a phenomenal success, too. Recently, Brandon’s book was a New York Times Bestseller, and he has more than 1 million Facebook fans.

While I can’t promise you’ll have that kind of success, if you choose a theme you’re excited about, it will inspire you to get started.

You don’t need a huge project either. You could start with 10 people. The numbers aren’t important; your passion is.

2. Find Your Spot

Photo by Martin Hricko
Photo by Martin Hricko

Pick a place with lots of relaxed people. Loitering near an office building at 8:55 am on a Monday is a great way to suck at street portraits.

Here are some good spots:

  • Tourist attractions: The more people with cameras, the better.
  • Farmers’ Markets: It’s the weekend, people are strolling, and stopping for a photo opportunity isn’t a big deal.
  • Art events: Creative people will understand what you’re doing.
  • Parks: Look for happy people sitting on benches, throwing frisbees and walking their dog.
  • Bars: I’m not saying feed your subjects drinks or anything, but a little booze won’t hurt to loosen someone up. 🙂

3. Choose Your People

Photo by Urban Scot
Photo by Urban Scot

There are three types of people:

A. Those who always want their photo taken.
B. Those who never want their photo taken.
C. Those who might want their photo taken.

You will get rejected, no matter how skilled you get at this. Brandon’s been shooting on the street for almost four years, and only two out of three people agree to have their photo taken, but that’s better than when he started. It used to be only one out of three.

Improve your odds by choosing compatible people. Steer clear of people walking fast, listening to their headphones, talking on their phone and staring dead-straight ahead.

Look for people who are:

  • Wearing colorful or fashionable clothing
  • Strolling casually
  • Laughing or smiling
  • Alone
  • Wearing their own DSLR camera

4. Ask Sincerely

Excuse me. Photo by Diego Angel
Excuse me. Photo by Diego Angel

If you’re working on a project you love, and you see something beautiful in a person…tell them. You might make their day. No one wants to be approached by a cheesy salesman though, so be sincere.

Brandon’s simple pitch is, “Excuse me, could I take your photo, just like that?”
He says it’s all about your body language and tone of voice though.

Here’s another pitch you could adapt, “Excuse me, could I take your photo for a project?” Then, when they ask you the inevitable question, “What’s it for?” be prepared with a few sentences about who you are, what you’re working on and where their photo will be used.

Even pull out your smartphone and show them an example of your work or your website. If you’re still nervous, bring a friend for support.

5. Practice, Practice, Practice

Keep trying. Photo by Magdalena Roeseler
Keep trying. Photo by Magdalena Roeseler

The first few strangers you approach will be tough. Keep practicing, though. It will get easier. You didn’t learn to take beautiful images in a day, and this will take time, too.

My fear never went away. I did learn to deal with it and a lot about talking to strangers. Plus, I have thousands of images and memories from meeting all sorts of people.

Sure, I met some rude people. But it’s remarkable how receptive people are to having their photograph taken. Most were touched or flattered. Others stayed in touch.

What’s helped you approach strangers and ask to take their portrait? Or do you have a question about taking photos on the street? Please ask in the comments below, and we’ll try to answer them personally.

By Benjamin Jenks

Benjamin Jenks offers creative strategies to help you live, work, and travel, like an adventurer at AdventureSauce.com.


  1. Great article! 🙂 People have to try stepping out of their comfortzone. I did that in 2011 during an event in my town (in The Netherlands). I never took photos of people before so it was quite an experience. I was feeling very insecure at the moment I took them, but the pictures turned out great. 🙂 The only one I’ve shared my photos with was the person behind this event and she loved the pictures! I didn’t need money for them, because it was just a hobby, but I got some. And one of the pictures (which I’m sending with this comment) even hit the local newspaper. Isn’t that awesome?? 😀

  2. Oh Melissa, that dude is a cutie 🙂 Cool moment you captured! Good point too, taking these street photos can be helpful to make connections with fun people and get your work out there

  3. Hi Benjamin,

    Great article! In fact, I will start with some street photography in one of the coming week ends! One question though; do you have any business cards on you to hand over to people afterwards? Or is this what you mean with being a “cheesy salesman”? 🙂 Cheers, Pieter

    1. Hey Pieter, I have handed out business cards, and I don’t think that’s being a “cheesy salesman” (unless you’re pushy about it). Seems like an easy way for them to remember your contact information and take a look at their shot.

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