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.

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

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.

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

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

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

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

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

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.