I recently photographed a Chicago engagement session with Julie and David that perfectly blended personal history, laughter, and stunning city views. We began in Old Town at The Vig, the restaurant where they had their very first date. Wanting to relive that special moment, we ordered martinis before starting the photos. Julie went for a classic dirty martini, while David and I opted for espresso martinis.

Within just minutes, the evening took an unexpected turn. David accidentally spilled part of his drink, and some landed on Julie’s pants. Rather than letting it ruin the moment, they both burst out laughing. It was the perfect icebreaker and instantly made the session feel more relaxed and fun.

From there, we strolled through the Gold Coast neighborhood, known for its historic brownstones, elegant streets, and charming details. I captured candid shots of them holding hands, walking under leafy trees, and sharing quiet glances. The natural chemistry between them made every frame feel effortless.

We wrapped up the session at Oak Street Beach, where the Chicago skyline rose behind them in the warm evening light.

I’m already excited to photograph their wedding next year—and curious to see if David might spill another drink on the big day!