Anatomy of a surprise proposal in Havana.
It starts weeks earlier, in an email thread she'll never see. It ends on a rooftop with champagne. In between: one question, on one knee, in the most photogenic city in the world.
Every few weeks an email lands in our inbox that we have to answer very, very quietly. It's always from him — or from her — and it always says some version of the same thing: I'm coming to Havana. I'm bringing a ring. She has no idea. Can you help me?
Yes. Always yes. Surprise proposals have become one of our favorite things to photograph, and over the years we've built a system for them — a friendly little conspiracy that runs entirely over email, between us and one nervous person with a secret in their suitcase.
The planning happens weeks before anyone gets on a plane. Over email we go over everything with the future fiancé: the date, the light, the route of the session — and, most importantly, the place. We suggest a few spots we know intimately: a quiet stretch of seawall at golden hour, a fortress overlook with the whole city glowing across the bay, a rooftop above the rooftops. Together we pick one, and from that moment there's a star on our private map. That's where it happens.
We work out the small logistics that make or break the moment: which pocket the ring rides in, where we'll be standing, what the cue is. Some people want family or friends hiding around the corner. Some want champagne waiting. All of it gets arranged in that email thread — the only person in Havana who can't know a thing is the one the entire plan is for.
On the day, we run the session exactly like any other. Classic car, old doors, the Malecón, the usual jokes, the usual posing tips. That's deliberate: the best camouflage for a proposal is a genuinely great photoshoot. She's thinking about the light and her dress, not about what's in his pocket. Our whole job in act one is to be so normal that suspicion never gets a chance.
The one with the star on it. We set up 'one more shot', step back to 'change the lens' — that's the signal. He reaches into his pocket and goes down on one knee, and we're already in position, already focused, already shooting.
“By the time she realizes what's happening, we're already shooting.”
The next sixty seconds are why we love this job. The hands flying to the mouth. The yes — sometimes whispered, sometimes shouted at the whole bay. The leap. The laughing and crying happening at the same time on the same face. None of it can be posed, and none of it comes back — you either catch it or you don't. We catch it.
And then, the first portrait the ring ever gets.
Every proposal session ends the same way: somewhere high, with something cold. A rooftop over Old Havana, the Capitolio catching the last light, a bottle we stashed there earlier. The adrenaline melts into celebration — the toast, the ring photos, the phone calls home with the same three words. This part of the session is pure joy, and it photographs exactly like it feels.
Some proposals are two brides-to-be above the harbor. Some come with a whole crew of friends hiding behind a classic car, waiting for the scream. Whoever you are and however you want to ask, we'll build the plan around you.
And once, Havana itself joined the plan. We were shooting a proposal across the bay when a full band — all in white, trombones to congas — happened to be rehearsing a few steps away.
They saw the knee go down, put two and two together, and broke into a serenade for the brand-new fiancés. Nobody hired them. Nobody could have. That's the thing about proposing in this city: you plan everything, and then Havana adds a little something of its own.
A proposal is a moment you'll want to remember for the rest of your lives — and it only happens once. We make sure it's captured in the most special way we know how: planned to the minute, shot like it wasn't planned at all.
Write to us and we'll plan it together over email — the spot, the light, the champagne, the hiding places. She'll never see it coming. He'll never see it coming either.
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