Brian and Jackie's Chicago Proposal

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how we met

Brian and I met randomly at a Matt and Kim and Passion Pit concert in Chicago. Seated between our two groups of friends was Brian’s overtly extroverted father, who wouldn’t/couldn’t stop dancing… I asked the dancing man whom he was here with and that was the first time Brian and I locked eyes. The rest of the night was a whirlwind of dancing, laughing, and drinks. From that night forward, Brian and I have been inspirable and partners in crime.

Brian and I met at the UIC pavilion but fell in love in Bucktown, a neighborhood filled with great food, great bars and great people. It was this combination of pluses that drove Brian and I to make Bucktown our home as we moved in together.

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how he asked

After almost three years of dating, Brian put together a secret plan to propose (finally). In order to put together the surprise proposal of my dreams, he enlisted the help of one of my best friends to in planning the perfect Bucktown proposal. The stage was set, brunch with the girls was all a rouse, and the secret photographer was ready and waiting on the 606 Trail.

I’ll never forget that morning; I thought that I was just going to meet the girls for brunch like we’d done 1000 times before, with one brief detour on the 606 to meet up with my friend and her son. As we were walking to the meeting place Brian was telling my how much he loved our life together, and while affirming all I could honestly think about was how amazing the new brunch spot was going to be. When we got to the bridge my friend was nowhere in sight, and I noticed Brian was fumbling around in his pocket. He then got down on one knee and pulled his hand out of his jacket pocket, and a opened a black box.

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Before he could say anything all I could say is “is this real, is this real?!?”. At the entrance to the Milwaukee St. bridge on the 606 Trail, the love of my life and my best friend asked if I would spend forever with him.

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I said yes…

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After the proposal, he had asked for us to “just enjoy the moment with each other” and if I would grab a glass of champagne to celebrate at a nearby watering hole. Of course the first thing I did was call my mom and tell her what happened, she explained how happy she was for us, and how she couldn’t wait to see the ring in person. When we walked into the bar the hostess nodded at Brian and as we turned the corner into the main seating area I was caught off guard by a booming “SURPRISE!” All of our friends and family were waiting for us to celebrate together; it meant so much to have the most important people in our lives together with us to celebrate the most important moment in our life.

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Special Thanks

Becky Brown Photography
photographer