Jack & Charlotte. A Proposal in Funchal, July 2026

The scene we agreed on

Jack and I agreed on a scene before he ever landed. I would not be the photographer they had booked. I would be a stranger who happened to be standing there with a camera.

No booked hour to explain, no meeting time, nobody waiting for them. They would walk into the old town, I would already be there, and I would come over and offer to take a few pictures the way a local photographer might.

I got to Forte de São Tiago early and photographed for myself for a while. Then a taxi pulled up and the two of them came into the courtyard, looking around at the yellow walls. July, the middle of the day, sun straight overhead, which is the light I would normally walk away from.

I went over and said they looked bright, which was true. Blue dress, blue shirt, the pair of them lit up against those walls. I offered a couple of frames and suggested we walk while we were at it. They said yes.

Then the plan came apart.

On the walk I asked Charlotte what kind of photographs she likes, and whether she liked the fort. The fort was where Jack and I had it planned, down to where I would stand. She said no. She wanted palms, greenery or flowers behind her.

So I improvised. We kept walking through the old town while I looked for a background that would do what she asked, with Jack a step behind us.

First a wall of dark leaves and white flowers, even light in front of it, no hard sun on faces. Then a lawn under tall palms.

Then I said our line. We had agreed weeks earlier that when I found the place, I would say we had found the perfect place and the light was good. That was his signal. He had the ring box out before I finished the sentence and went down on one knee on the lawn.

Charlotte did not expect it. Her hands went to her mouth, then to her cheeks, then to his face. The frames below are in the order it happened.

It was tender and full of feeling, and a celebration at the same time. I like the sessions where it all comes off, when the happiness is theirs and mine at once.

After that nobody had to act. We walked slowly and the session carried on along the palms and the seafront, on what was left of the moment.

At the end of it we did get to the fort she had turned down an hour earlier, and it photographed well.

Three things made this one work.

Jack set it up weeks ahead. A stranger walking over with a camera is only believable if the stranger knows exactly what he is doing there and what the signal is.

The place was busy. In the old town a photographer offering pictures is an ordinary sight. On an empty clifftop it is not, and the same approach would have looked staged.

And he kept track of where I was standing. When he went down he turned so the two of them were side on to me. That is why both of their faces and the ring are in the frames of the proposal above.