Emily and Matthew

Emily and Matthew's Engagement in Chicago, IL

How We Met

On Sunday, August 7, 2016 my family (Emily) was finishing up our weekend spent up at our Uncle Kurt’s cottage on Stoney Lake when a couple of young guys showed up, friends of Kurt’s niece, to enjoy some wake surfing. Little did either of us know we would be spending forever together.

As we prepared to go out on the boat, the only words I uttered to Matt were “How do you know Kurt?,” to which he responded promptly. He impressed me with his wake surfing abilities while I failed miserably, despite the fact that earlier that day I was doing quite well. Although I found him very attractive, I thought there was no way he was single. We got back to the cottage and packed up as I had a date that night back in my hometown. As soon as Kurt found out that I was leaving for a date, he informed both my mother and I that Matt was not only single but also a new doctor. So of course my mom made me go say goodbye to him and his friend although it felt extremely awkward and forced. Not only did she make me say goodbye, she made me friend him on Facebook a few days later. I drew the line there; I would friend him but nothing more.

A couple of weeks later, our family went on a trip to Niagara Falls, finally giving Matt an excuse to slide into my DMs on Facebook. Meanwhile, I was at my parents house recovering from surgery and binge watching ‘Prison Break’ with my mom when a message from him showed up on my phone…. and I may have squealed when I saw it and immediately showed my mom. As to have a topic of conversation, Matt started watching Prison Break despite being in the midst of a grueling rotation at the hospital, and not too long after, asked me on a date. Little did we know, August 30, 2016, would be our last first date ever!

Where to Propose in Chicago, IL

Proposal Ideas Chicago, IL

How He Asked

Up until a year ago I had never been to Chicago. Even though we only live a few hours away, I had no real desire to go. That was before I met Emily. Emily is in absolute love with Chicago. She has been there over a dozen times. She even told me she could see herself living there one day. A year ago I had the opportunity to go to Chicago to celebrate my Uncle Kens birthday. Emily was so excited to take me. She planned out so many activities for us to do. I ended up having a great time and since that day we have been back 3 or 4 times. When I was thinking about how to propose I knew that it had to be in Chicago. The trouble was, Emily would have known I was going to propose if I told her I was taking her there.

So to be sneaky, I had Emily’s best friend Jory plan a shopping trip for the two of them in Chicago. What Emily did not know was that I was behind the whole thing. For a month I planned out how to surprise her when she was “shopping”. I came up with our 5 favorite places and wrote her a love note for each one. I had planned a scavenger hunt style date before for Emily and she loved it. I did feel a little bad that I had to keep Emily in the dark about that day though. Especially because she is the worlds number one planner and had an entire day planned out for her and Jory. As Emily and Jory left for Chicago, I picked up Jory’s husband Matt Grooters and we headed there at the same time. I was extremely nervous. So nervous that I almost ran Matt over when I was parking the car. Luckily I didn’t because that would have changed the entire day. Sorry about that Matt.

Matt Grooters and I surprised Emily and Jory at the mall. I walked up behind Emily and gave her a hug and a kiss. She was so startled I thought she was going to slap me. I think she instantly knew what was going on. But I did not propose yet. We left Matt and Jory and went off for a day on the town. We went to our favorite rooftop bar, the bean, ghirardelli’s, the Navy Pier and then went to Lincoln Park Zoo. A year ago we took a picture on a bridge at that zoo and it is one of my favorite pictures of Emily. Emily is holding my niece Rylee on a bridge overlooking the city and there is so much joy and love in both of their eyes. That picture inspired me to make this the spot I would propose.

When we got to the zoo I still had two letters left for Emily. She didn’t expect this to be the spot that I would propose. We walked around and saw a few of the animals but I was so nervous I hardly said more than a few words. When we made it to the bridge, Jory and Matt were hiding to take pictures of us. I gave Emily the last letter and in it I told her that she was person I wanted to spend the rest of my life with. I made her read it out loud and I wrote that I had one more question to ask her. I got down on one knee and asked if she would make me the happiest man alive and marry me. As she broke into tears she shook her head yes and pulled me back up to kiss me. It was the happiest moment of my life.

A year ago I would never have guessed I would be asking Emily to marry me in Chicago. But God works in amazing ways and on December 16, I made the best decision of my life and proposed to Emily in the city that she loves. It was the best day of my life, and now I love that city just as much as her.