Downtown Winnipeg
Deril's Proposal to Annie

A Month in the Making — The Setup

The first time Deril reached out, he didn't have a specific idea — just a clear intention. He wanted Annie to walk into something she couldn't have imagined, in a space that felt completely outside of ordinary life. We talked through options. We mapped out a timeline. We went through the logistics of how to get a photographer into a private space before the subject arrives without anyone tipping her off. We landed on a historic private building in the downtown Winnipeg core — and then started building the rest of the plan around it.

Over the course of the following weeks, the details came together. Twin floral arches commissioned from a local florist: blush peonies, garden roses, ranunculus and greenery, cascading from floor to ceiling on either side of a marble antique table. Dozens of LED pillar candles arranged across the table surface and scattered across the marble floor in concentric rings. Rose petals — hundreds of them — placed one by one across the mosaic tile. A catering spread for the family and friends who would be waiting, hidden, in an adjacent room. All of it coordinated through a chain of calls and messages that somehow stayed secret from the woman who would walk through the door and into the middle of it.

I arrived early. Shot the space empty — the arches, the candles, the petals on the marble — while it was still quiet. Documented every detail Deril had put into motion. Then I found my position and waited.

She Had No Idea — The Proposal Moment

Deril led Annie through the building — past the stained glass entry, through the corridor, toward the rotunda. The cover story: there was something he wanted to show her. She had no reason to suspect anything. And then she turned the corner and saw the flowers.

The reaction is always the thing you can't plan for, no matter how well the rest of the setup goes. Annie stopped. Took it in. Turned to look at Deril standing beside her. And then he was already moving — taking her hand, walking her toward the arch, saying the words he had rehearsed and felt at the same time. She was still processing the flowers when he got down on one knee.

From my position, I had the angle — the floral arches framing them, the chandelier above, the marble and candles and rose petals below. I moved as they moved, found the compositions as they unfolded. The close moment. The wide shot with the full setup behind them. The look on Deril's face when she said yes. That expression doesn't exist any other way — you can't manufacture it. A month of planning, hundreds of logistics calls, and it all compressed into a single moment in a marble room in downtown Winnipeg.

She said yes.

She Said Yes — The Celebration

And then the door opened.

Family and friends had been waiting — quietly, for longer than anyone admits is comfortable — in an adjacent room. The moment Annie said yes, they came through. The sound that followed was the best kind of chaos: laughter and tears colliding, everyone reaching for Annie at once, Deril watching with that specific expression of someone who pulled off the thing they weren't sure they could pull off. The kind of relief that looks exactly like joy.

I switch to a different mode for moments like this. The poses are gone — there's nothing to direct. It becomes documentary work: move through the room, find the frames as they happen, stay out of the way. A friend hugging Annie so hard they're both shaking. Deril grinning at someone across the room. Parents seeing their kid newly engaged. These images don't come from being told where to stand — they come from being in the room when it happens.

Above the Skyline — Rooftop Portraits

After the celebration settled, Deril and Annie slipped away from the group and we took the stairs up. The rooftop terrace opened onto the downtown Winnipeg skyline — towers of glass and concrete spreading out in every direction, overcast light pressing evenly across everything, the city quiet above street level. Annie still had the champagne. They poured a glass each and toasted in front of the view.

Rooftop portraits after a proposal have a specific quality that's hard to manufacture in any other setting. There's still adrenaline in the room — or in this case, in the air. Both of them are still processing what just happened. The ring is still new on her hand. That combination of fresh emotion and open sky produces images that feel genuinely alive. We danced. We leaned. We let the city take up the background while the two of them found each other again in the quiet after the chaos.

The bronze sculptures on the terrace, the art on the walls, the rooftop steps with the Winnipeg skyline behind them — the space had layers that revealed themselves slowly as we worked through it. By the time we finished, we had covered the whole terrace. Then we went back inside.

The Grand Staircase — Portraits Inside

We came back inside as the evening settled. The interior staircase — ornate wrought iron with filigree detailing, candles placed on every landing — was waiting for us. Somewhere between the rooftop and the staircase, something in the session had shifted: the intensity of the proposal had given way to something quieter. They were just together. Just themselves. The staircase gave us the light: the warm glow of candles against the dark iron, the architectural detail of the building doing the work that any outdoor location would need sky and trees to do.

I switched to black and white for portions of the staircase portraits — the candlelight and the iron and the stone all resolve beautifully in monochrome, and there's a timelessness to those images that colour can sometimes work against. We worked the full length of the staircase: from below, looking up at them against the archway above; from above, looking down at them on the curve of the steps; close, with nothing but their faces and the glow of the candles behind them.

It was a night worth documenting. A month in the making, two hours in the living, and images they'll have for the rest of their lives.