How to Approach Strangers for Street Portraits

Ever stand on a street corner, camera in hand, frozen in place? You see a face you need to photograph—one of those once-in-a-lifetime characters—but instead of walking up, you hesitate. You start thinking: What if they say no? What if I make a fool of myself?

Here’s the truth no one likes to admit: the only way to get better at approaching strangers is to do it—especially when you don’t feel ready.

This blog is based on a recent podcast episode I recorded | PODCAST EPISODE

Stop Waiting to Feel Confident

Most photographers wait for the perfect day—the day they’ll suddenly feel confident, bold, unstoppable. But that day never comes. Confidence doesn’t show up first. Action does.

The reality? Every photographer feels the same fear. That hesitation, that “what if they tell me to piss off” voice in your head—it’s just mental furniture. Rearranged differently from person to person, but it’s still there.

The trick is to go for it anyway. The fear never fully goes away. You just stop letting it drive.

Why Fear Is Actually a Good Sign

Here’s the weird thing: when I feel that knot in my stomach, that slight edge of fear—that’s when I know I’m about to get something good.

If I’m comfortable, I’m probably not pushing it. Safe photographs are boring photographs. Fear means you’re stepping outside your comfort zone, and that’s where the good stuff lives.

Throw a Glitch in the Matrix

Most people live on autopilot. Same commute. Same takeaway on a Tuesday. Same Netflix show before bed. They’re basically wired into the matrix of routine.

So when you stop them in the street and say, “Excuse me, can I take your photograph, please?”—you’re talking pretty much to their script. And the script nine times out of ten will say … “No.”

Want to change the answer? Change the script.

Be playful. Surprise them. Make them laugh. Do something unexpected.
You’ve got to throw a glitch in their programming so they actually see you—and that’s when real human connection happens.

Make It a Collaboration, Not a Transaction

Every portrait is a collaboration. If you’re not holding up your end how can you expect a perfect stranger to hold up theirs.

Before you even open your mouth, check your body language. Are you open, relaxed, genuinely curious? Or are you tight, hesitant, hiding behind the camera?

People can feel energy before they hear words.
If you’re confident and excited, they’ll mirror that.
If you’re nervous and apologetic, they’ll mirror that too.

So go in with a bit of spark. Show them you actually want to photograph them, not just tick off another shot. This isn’t just photography—it’s human connection.

Don’t Accumulate the “Nos”

People say no all the time. It’s not personal.

If someone turns you down, you’re still in the same place as before—you don’t have the shot. So nothing’s really changed. Don’t let rejection pile up in your head.

Street photography is about repetition and consistency. You build your rhythm through action. You go again. And again. And again. That’s how confidence actually grows—by doing the uncomfortable thing over and over until it becomes normal.

black and white photo of man smoking cigarette

Be Playful. Get Your Hands Dirty.

Street photography isn’t a polite sport. It’s messy, unpredictable, and that’s what makes it fun.

Every time I go out shooting, I’m right on the edge of my tether. I never feel ready. But that’s where the gold is. That’s where the magic happens.

So mix it up. Change how you move. Change how you ask. Change how you see.
Get a bit dangerous with it—with your attitude, your approach.

Over and Out

Look—if you want to take powerful street portraits, you’ve got to meet people where they are, and sometimes that means shaking them awake a bit.

Bring your humanity. Bring your curiosity. Be bold, but be kind.

SUMMARY

This article explores how to approach strangers for street portraits with honesty, humour, and heart. It shares a mindset for overcoming fear, building confidence, and connecting deeply with people you meet on the street. Through real-world insights and a conversational tone, it helps photographers understand the psychology of human interaction, offering creative strategies to make authentic, emotional portraits that stand out in the world of street photography.