How Asking Strangers for Portraits Helped My Photography

How I Got Over My Fear of Asking Strangers for Portraits And Why It Helped My Photography

Street photography has been a big part of my journey as a photographer, especially when I first got my film camera. I remember one of the first three photos I took was of a couple of guys handing out flyers for their clothing brand. I asked them if I could take their photo while they were promoting a popup event. That moment was a turning point for me not just in terms of the photo itself, which I still think looks timeless, but because it started me thinking about how I interact with people through photography.

Taking portraits of strangers isn’t always easy. Early on, I was shooting lots of candid street photos, snapping interesting people or moments without really engaging. I’d watch, I’d capture, but I wasn’t connecting. I wanted to change that. I wanted to walk up to someone and say some version of “Hey, I think you’ve got a cool vibe I’m a photographer, would you like a portrait?” But the idea of approaching strangers felt intimidating.

For anyone who does portrait photography whether newborn, maternity, solo portraits, or general sessions interacting with your subject is a huge part of the job. Even with newborns, where you can’t really chat with the baby, you talk to the parents, you guide them. With maternity and solo portraits, building trust and comfort is crucial to capturing genuine moments. So overcoming my fear of approaching strangers on the street ended up helping me build confidence across all my portrait work.

One of my first street portraits. Still feels Timeless especially as it was shot in B&W - Shot in Dalston, London

Meeting Vicky - “Fight your demons”

I met Vicky through Bumble Bizz while I was in London. She’s the studio manager for Cristina de Middel a well-known Spanish and Belgian documentary photographer & Magnum Photos member. We talked about photography, and I shared my struggle about wanting to take more portraits of people but feeling too afraid to ask. She was surprised and asked if I was shy about approaching strangers. When I said yes, she encouraged me to push through that fear. “Fight your demons”! 

The next day, I was out walking around London and decided to try. I approached a guy and asked if I could take his portrait. He said no, and I felt discouraged. When I met Vicky again, I told her what happened. She shrugged and said, “Well then he just wasn’t the right person.” That stuck with me.

As she left I approached two guys sitting on a bench and asked if I could photograph them. They said yes, and as I walked away, I heard them say, “It’s like something from TikTok!” It was such a small moment, but it gave me a boost. From there, I started asking more people, and most of them said yes. I still had to psych myself up to ask, but it got easier.

That moment gave me a boost, but I also noticed something else sometimes people hesitate when I first ask. I could sense their uncertainty, like they weren’t sure if they wanted to be photographed. When that happened, I’d show them some of my previous portraits on my camera or phone. More often than not, that helped them relax and say yes. It’s amazing how seeing the work can build trust and break down those initial walls.

“It’s like something from TikTok” - Outside of Magnum Photos in London

“Fight your Demons” -

What Asking Strangers Taught Me About Portraiture

I’ve learned not to take it personally when someone says no. I remember asking a guy once who declined not because he was unfriendly, but simply because he didn’t think he looked good that day. On the flip side, many people have told me that I made their day by asking. 

Whether it’s a newborn shoot where parents are nervous or a solo portrait where the subject isn’t used to being in front of the camera, it’s all about creating a comfortable space.

Asking strangers pushed me to be more confident and direct, which helped me in all my photography work. When I do newborn or maternity shoots, I’m much more at ease chatting with parents, making them feel relaxed, and capturing real moments. When I do solo or couples portraits, that confidence shows, and people respond well to it.

It’s also taught me to be more flexible and empathetic. People come with different boundaries and feelings about being photographed. Understanding that and adapting whether on the street or on location makes a difference between a good session and a great one.

Creative Interactions and Unexpected Connections

One of the coolest parts of street photography is the unexpected connections it brings. I remember once taking a photo of a guy on film he heard the distinctive shutter sound and turned around immediately, smiling. We ended up talking, taking pictures of each other. Moments like that remind me how photography is more than just capturing images it’s a creative exchange.

I’ve met some incredible people through this practice. Sometimes the people I photographed have to events I’ve hosted later, or we end up staying in touch. These interactions enrich my life and my work, and they’ve inspired ideas for future projects like a series combining portraits of strangers and people I know. More on that later. 

I heard that sound & I knew it was a film camera” - Charles

Taken by Charles

Bringing This Into My Photography Business

My experience with street photography and asking strangers has had a big impact on how I approach all my photography sessions newborn, maternity, solo portraits, and more. Talking to people, building trust, and being confident in asking for their portrait make a huge difference in the quality and feel of the photos.

Whether I’m shooting outdoors, at events, or on location, I know that great portraits come from connection. When parents feel comfortable with me during a newborn shoot, the natural moments shine through. When someone’s nervous about maternity photos, I can help ease them and create a relaxed environment. And when I meet someone new for a solo portrait session, I’m confident in my ability to engage and get authentic expressions.

For photographers looking to improve their people skills, I highly recommend pushing yourself to talk to strangers, even if it feels scary. It doesn’t have to be perfect, and you don’t have to succeed every time. But each interaction builds your confidence and helps you develop the communication skills that are vital for every portrait session.

Maternity Shoot

Why It Matters to Me

I’m inspired by projects like Humans of New York, which show the power of simple conversations and portraits. It’s not about capturing perfect images alone, but about capturing stories, personalities, and moments. That journalistic aspect is something I’m interested in exploring more simple questions, quick portraits, and sharing small pieces of people’s lives.

Photography, to me, is a way to connect, to imprint my view of the world through a photo and to learn from those brief but meaningful encounters. Overcoming my fear of asking strangers for portraits wasn’t just about getting photos it was about growing as a photographer and as a person.

Diana from Mexico - Shot outside the Tate Modern in London

Final Thoughts

If you’re a photographer, whether you shoot newborns, maternity, couples, or solo portraits, I encourage you to step out of your comfort zone and engage more with the people you photograph and even those you don’t yet know. Every interaction is an opportunity to learn, to connect, and to create something real.

It’s not always easy I faced rejection and nerves but each step forward has made me better at what I do. And it’s helped me see that portrait photography is as much about people as it is about the camera.

So next time you hesitate to ask for a photo, remember: the person who says no isn’t the right person. Keep trying. “Fight your demons” & You’ll be surprised where it takes you.

“Some people have FOMO. I have JOMO” - Vicky