Jessica and Christopher

Image 4 of Jessica and Christopher

How We Met

Chris and I met online in 2016. We exchanged witty banter for a while and on his third as I decided we should meet in person. Our first date was October 8th. We met on the Chicago Riverwalk. We hit it off immediately. A walk turned into a drink, then a meal, then a long walk, then another meal. Neither of us wanted the day to end. We met at 4 o’clock in the afternoon and we said goodnight around midnight. We spent almost every day together moving forward. After about 7 months we moved in together. In that time we had traveled to Washington DC, Alaska, Nevada, Wisconsin, Canada, and Wyoming together.

Several months after we started dating, we spent our first Valentines’ Day together. I had just returned from a visit home and I was reluctant to go over because I was so tired. Unbeknownst to me, Chris had cooked me a huge meal for the first time ever and included all of my favorite foods. He had been listening closely. I went over to his house and he had a huge beautiful bouquet of flowers for me, a big present and this elaborate meal with champagne. I felt guilty for even thinking to postpone the Valentine’s Day celebration! I had never been put on a pedestal this high. He made me surf and turf, king crab legs, roasted carrots with honey drizzle, salad with mango, and asparagus with lemon. It was amazing. As though that weren’t enough, he had this big beautiful gift bag sitting by my flowers. After dinner and champagne, he urged me to open it. Inside we’re these adorable mittens with hearts on them. He asked me to try them on to make sure they fit. Inside the mittens, he had stuffed an envelope with a letter saying we were going to Jackson Hole for a ski trip. It was the most magical Valentine’s Day ever. He had handmade the card also! It was a colored paper blue and pink (favorite colors) elephant with its trunk as the “J” spelling out Jessica across its body. I cried. It was so thoughtful. The gloves were a little small so we went to the Burton store to return them a few days later. When we took them to the counter the clerk ask if his name was in the system. He gave them his last name and the woman asked, “is your name Wolfgang”? “No, I wish!” Chris said. From that day forward we decided our first son’s name would have to be Wolfgang. We started coming up with boys and girls’ names from that day forward.

How They Asked

Three years later, we had just returned from a two week trip to Germany, Austria, and Hungary. We had been to countless castles and mountaintops. Perfect places for a magical proposal. When we got home, I was disappointed he hadn’t proposed and resigned to thinking he wasn’t ready. For our anniversary, a few weeks later, he had made a reservation at one of our favorite restaurants, which was not out of the norm.

Image 3 of Jessica and Christopher

I had returned that afternoon from a work trip and rushed to get ready for dinner that night. I also had to pack for another trip I was leaving for the next morning. So as he rushed me out the door, my mind was somewhere else. On the way to dinner, the Uber stopped at a red light and Chris asked if I wanted to hop out to walk the rest of the way. It was a beautiful fall day, so I said yes, of course.

Image 1 of Jessica and Christopher

We walked along the Riverwalk and chatted about my week and his. When we got to the spot we first met, he stopped and turned me around to face him and dropped to one knee. I don’t remember if I cried or screamed. I was so happy I said yes before he finished proposing. It was magical.

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He was so nervous he had put the ring on the wrong finger. He had hired a photographer to capture the proposal. When we had finished crying and hugging he turned me around to introduce me. I can’t believe I didn’t see him and his huge telephoto lens!

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The photographer was amazing. He introduced himself and explained how we would do the engagement shoot. “First,” he said, “let’s get this ring switched over to the right finger.” After the engagement shoot, Chris and I walked over to the Café where we had our first date and toasted with champagne. We quickly called our parents to tell them the news before walking to dinner.

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Image 7 of Jessica and Christopher

I think I had anticipated the proposal being on our trip that I didn’t expect it right after! It was perfect and thoughtful, so perfectly Chris. He had proposed in the exact spot we first met, three years later. We went to bed so happy and in love and heartbroken that I had to leave the next morning. I only got to call my babe my fiancé for a few hours before saying goodbye. We planned our wedding for the same date, one year later, on October 8th, 2020.

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Special Thanks

Collin Pierson
 | Photographer