I truly enjoy capturing engagement sessions for many reasons. They allow me to spend time getting to know my couples, help them feel comfortable in front of the camera before their wedding day, and create space for creativity without the pressure of a tight timeline. This freedom is a big part of what makes engagement sessions — and especially Chicago engagement photography — such a meaningful experience.
But some moments go beyond engagement sessions — like real proposals.
A few months ago, I received a text from Brandon, who was planning to propose to his girlfriend, Dannah. He was looking for someone to quietly capture this once-in-a-lifetime moment. From the details he shared, I could already tell how thoughtful and intentional his plan was. All that was left was to wait for the custom engagement ring to be completed by his jeweler.
A couple of days later, I got the call — everything was ready. Because of the short timeline, Brandon and I didn’t have a chance to meet in person beforehand, so we had to play much of it by ear. The night before the proposal, Brandon sent over a few photos of himself and Dannah. That’s when it clicked — the Brandon I’d been coordinating with for days was Brandon Bollig, former NHL player for the Chicago Blackhawks and San Jose Sharks. The excitement definitely grew… and so did my nerves.
On the day of the proposal, I arrived early at the beach, set up my camera, and took a seat on a nearby bench, doing my best to blend in. My camera was tucked discreetly behind my bag as I waited, looking like just another person enjoying a quiet day by the lake.
Soon, I spotted their car pull into the nearby parking lot. As Brandon and Dannah walked toward the beach, I made a conscious effort to look anywhere but in their direction — the last thing I wanted was to accidentally give away the surprise.
They passed just a few feet from me. Once they were far enough ahead, I carefully pulled out my camera and began capturing them as they walked along the rocky shoreline. Brandon led Dannah toward the end of the dock, and that’s when the moment happened — genuine, emotional, and completely unforgettable. Being there to document it was an absolute privilege.
After the proposal, we spent about 45 minutes creating relaxed, creative images together — photographs they can now use throughout their wedding journey and beyond.
