This couple’s Chicago proposal included a surprising moment.

Philip and Katie’s Chicago proposal included a shocking moment…besides that whole surprise proposal part! Why did their proposal photographer think the engagement ring was lost forever? And…well, was it? Read on for the sweet, as well as the shocking, details of their Chicago engagement.


Katie and I met through while she was touring with a North American Broadway show. I sent her a message to see if she wanted to go to the Cubs vs. Cardinals season opener that evening. She, being a Cubs fan, said she was already going, but could use a “bodyguard.” I agreed and picked her up after her show. We ended up not being able to get tickets, but wandered around until we found ourselves in BallPark Village to try to catch the last few innings. Before long, we were lost in conversation and forgot about the game completely. (It even started to rain!) The date went great and I asked if I could see her again. She sent me the rest of her touring schedule and I decided I couldn’t wait to see her, so I scheduled a flight out to Boston for the very next weekend. After some terrible travel luck and a flight to the wrong city, I rented a car and drove to Boston. We celebrated all weekend and decided to make our relationship official. After dating long distance and seeing each other as often as we could, I asked Katie if she’d like to move to Saint Louis. She was planning on going back to school to become a Physician Assistant after her tour. By August, we drove all of her things down from Manhattan and she was officially an STL resident. Month after month, the relationship grew. We joked about making it official, but between her crazy full-time student and full-time job schedules and my Marine Corps schedule, we never had a day off together.


My buddy’s upcoming wedding weekend was the perfect opportunity to plan a Chicago proposal. It was the only weekend Katie and I would have to ourselves. She hadn’t had a day off in six months and I had a very busy schedule as well. Katie also lived in Chicago for a couple years and loves the city.


Francisco was perfectly perched on the steps of the Riverwalk. I had convinced Katie that I wanted to see the “touristy” parts of Chicago and she was excited to walk the Riverwalk with me prior to a nice dinner reservation I had set up for us. Little did she know that halfway through the walk, I had planned a sneaky surprise proposal. Just before the Clark St. Bridge, I stopped her and told her that I had lied about the reservation. Shocked, she didn’t really know what to think. I got down on one knee, told her I loved her, and asked her to marry me. She said yes! Relief was an understatement, but there was still one more step. Katie wears her mother’s Tiffany sterling silver ring on that finger. I jokingly told her it was “probably time to take the old ring off.” She laughed and removed the ring…only to have it slip from her fingers, bounce three times, and fall into the Chicago River. We were both shocked, but we laughed it off and considered it a sacrifice to the wedding gods. After all, our Chicago proposal wouldn’t really be “us” without a crazy story to tell.