Oak Street Beach, Chicago
A Surprise Proposal at Oak Street Beach
Mayes planned to ask Kristen to marry him on the sand at Oak Street Beach, the downtown skyline behind them and the last of the evening light coming in off the lake. What Kristen did not know was that the night held two surprises, not one.
The plan behind the surprise
Kristen thought they were meeting friends for drinks at the beach bar, then heading to dinner, just the two of them. That was the cover story. In truth, Mayes had been planning this for weeks. A couple of trusted friends arrived early to set the scene on the sand: a blanket, white roses, a wooden crate lined with linen, a bottle of champagne, and two glasses engraved with the couple's initials and the date. Once everything was in place, they slipped out of sight. More of the people closest to them had flown into Chicago for the night and were waiting nearby, and Kristen had no idea any of them were in the city.
The part I plan for
A proposal happens once, and it happens fast, so most of the work is done before anyone picks up a camera. I arrived early to scout the sand, read the light, and find the spot where the setup, the skyline, and the evening sun all worked together. When his friends arrived, we placed everything exactly where the photographs would live. From the moment Kristen was near, they were strangers to me, no glances and no greetings, so nothing gave the secret away. Mayes sent me a quiet text as they came through the tunnel under Lake Shore Drive, which gave me a five minute head start to be in position and ready. A background in theater taught me how to stay out of sight until the moment arrives, and how to help people feel like themselves once it does.
The moment
Mayes walked Kristen toward the blanket and began to tell her the truth as they approached: that there were no friends coming, and why this was the day he had been waiting for. When he knelt, the drinks-with-friends story fell away and the real reason came into focus. Kristen said yes in blissful disbelief, all smiles and tears of joy.
The part you cannot plan
Some of the best moments are not on any shot list. After the yes, while we were making portraits along the water, an ice cream cart rolled past. I asked Mayes and Kristen if they had a sweet tooth, the answer was an immediate yes, and I grabbed them two celebratory Good Humor Strawberry Shortcake bars. It is a small thing, but it loosened everyone up and gave us a few of my favorite frames of the night. I do this often. Over the years I have handed couples street tacos, lemonade, donuts, and more, because a little spontaneity, read from whatever the moment offers, is part of how I work. Consider it a quiet perk: you might just get fed. Later, what Kristen thought was a quiet dinner for two became a room full of the people closest to them.
Jeremy was super friendly, knowledgable, and all around a great guy! He captured every moment of my surprise proposal perfectly, and we had a great time shooting additional photos afterwards. I would highly recommend Jeremy to anyone looking for a proposal photographer, he was incredible!!
Mayes, Oak Street Beach proposal
From the question to the vows, I love being there for the whole story. I have photographed 300+ proposals across Chicago since 2019, and a Jeff Award winning background in theater shapes how I work: quietly, with care, and with an eye on the light. If you are planning your own Chicago proposal, I would be glad to help you plan the moment and capture it. You can see how I work with couples here.