Part 2 of 5 in a Portraiture Series from Cuba
There’s a moment—when you’re shooting portraits—where everything goes quiet. Not because there’s no noise (Havana is never quiet), but because you fall into a kind of lock. A stare. A gaze.
And in that moment, something passes between photographer and subject that can’t be rehearsed, posed, or performed. It just happens.
Today’s post is about that gaze.
Each of the five models I worked with in Havana was hired. Paid. Professional. And damn good at what they do. These weren’t amateur influencers or tourists trying on Cuba for an afternoon. These were working artists—many of them dancers, actors, or musicians—who understood how to hold their body, how to play with light, and how to read the room… and the camera.
I don’t remember their names. That’s not the point of these posts anyway.
This series isn’t about who they are—it’s about how I see them.
And more importantly, what I see in myself when I photograph them.
The woman you see in today’s portraits gave me a gift I didn’t ask for but instinctively knew how to accept: She held her gaze.
Not in that dead-eyed, over-posed, fashion-model kind of way.
Not in a “Blue Steel” parody of emotion.
Her gaze was steady. Strong. Slightly curious.
Like she wanted to know something about me, too.
It wasn’t flirtatious. It wasn’t confrontational.
It was something more rare: Present.
That kind of eye contact in a street portrait—especially when the backdrop is loud and unpredictable—demands a mutual trust. It doesn’t matter how experienced a model is, or how technically capable the photographer might be. You can’t fake connection. And you can’t manufacture the gaze. It either shows up… or it doesn’t.
That’s why I move quickly.
Always have.
I don’t over-direct. I don’t storyboard scenes.
I don’t ask for too much.
I simply look for the moment when the gaze appears, then I press the shutter. And sometimes, if I’m lucky, that gaze looks back through the lens and out the other side—straight into the viewer.
That’s when I know I’ve got it.
Let’s talk a little gear and workflow—because I know many of you care about that, too.
Everything in this series was shot on the iPhone 16 Pro Max, using a variety of native focal lengths. Most of the time, I bounced between the 1X, 2X, and 5X lenses, depending on how close I wanted to get, and what kind of compression I was going for.
I did very little editing. A slight tweak here or there for exposure, shadows, or warmth. But most of what you see in this mini gallery is straight out of camera.
That’s important to me.
Because when the eyes say everything, you don’t need to dress the photo up.
You need to let the silence do the work.
Let’s also talk ethics, since portraiture always brings that question with it.
These were paid, permission-based sessions. Every model agreed to the shoot, understood the context, and collaborated with me fully.
But even with permission, there’s still a sacredness to photographing someone’s face.
Especially when they look back at you.
And that’s what today’s theme is really about:
Not just the model looking at me—but me actually being there to receive it. To respect it. To frame it. To not flinch when someone offers you a raw, unwavering piece of themselves through nothing but the eyes.
Because when someone gives you that gaze, the one that doesn’t break or blink, you better know how to honor it.
You better know how to make it count.
Havana is a city that never turns away.
You see it in the cracked sidewalks, the peeling paint, the humid air, the rusted Buicks, the sea spray, the stoops, the music, the dancing.
But most of all, you see it in the eyes of its people.
That’s why I keep coming back.
Because in a world that often looks down, away, or past—you can always count on Havana to look right at you.
And in that gaze, you’re reminded of something you can’t quite explain.
Something real.
Tomorrow: Day Three.
New model.
New energy.
New visual theme.
But for now, spend some time with these frames.
Don’t rush them. Don’t scroll past.
Let them look at you.
And if you feel yourself looking back?
That’s the point.
Click.
Jack.
P.S. Join us December 2-8, 2025. for an iPhone Photography workshop. So you can learn to take pictures just like this
