Proposal at The Bean in Chicago

How We Met: Kyle and I met in Chicago in 2009 through some mutual friends. My dear friend, Amy, and Kyle were coworkers. One night, Amy and I were out celebrating a friend’s birthday. As the party was winding down, Amy’s coworkers (including Kyle) convinced us to meet them for drinks at Citizen Bar. Kyle and I had a nice conversation, but I had a boyfriend at the time, so I was not looking for love that night. I saw Kyle a few more times that summer, but we were nothing more than friends.

Chicago Proposal

I moved back to Pittsburgh in September to be closer to my family, and soon after, broke up with my boyfriend. Coincidentally, Kyle’s company transferred him to its Pittsburgh office in January 2010. Kyle was new to the city, and hadn’t had a chance to meet a lot of people yet. I was going out with some friends one night, and thought it would be a good opportunity to invite Kyle to come out with us. I even tried to hook him up with a friend, but after awhile, I noticed he was more interested in me! A few Cubs vs. Pirates baseball games, mini-golf contests, and running dates later, we were dating and life couldn’t get much better!

how they asked: Completely unbeknownst to me, Kyle began planning our perfect proposal in January while I was out of the country on a business trip. He respectfully asked my father for his permission, and my father agreed. With that first step complete, Kyle began planning the biggest surprise of my life.

Having both lived in Chicago, Kyle and I take as many opportunities as we can to go back to visit. We decided a St. Patrick’s Day celebration was as good a reason as any. We flew out to Chicago on Thursday night, and planned to stay with Amy for the weekend. She had to work on Friday, so I planned a few things for Kyle and I to do around the city during the day. We had a great day touring Wrigley Field, having lunch in Lincoln Park, and creating our own perfume & cologne at Aroma Workshop. We returned to Amy’s apartment to freshen up for our dinner reservation at Park Grill. The restaurant is located in Millennium Park, underneath the famous public sculpture, Cloud Gate (aka The Bean). Since Kyle had never visited The Bean before, he wanted to leave some time before our reservation to stop by on our way. I had been there many times, but agreed, despite it being quite cold and raining that day.

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We walked arm in arm, huddled under my umbrella through the park and up to The Bean. I grabbed my phone and took a few pictures of our reflection, like all tourists do. Kyle hugged me and turned me around so my back was to The Bean. He handed the umbrella to me, dropped to one knee, and asked me to marry him! I was so surprised and I cannot remember anything he said, but I do remember responding, “of course I will!” After admiring my gorgeous ring, and plenty of hugging and kissing, Kyle introduced me to Kurt – the paparazzi-style photographer who had been secretly snapping pictures of us the entire time we had been in the park! I was so happy Kyle had arranged for Kurt to be there to capture our moment. It was perfect!

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Proposal at the Bean


We celebrated our engagement with dinner and champagne at Park Grill, and I called my mom to tell her the good news! She had been in on the secret, so she wasn’t surprised, but was ecstatic nonetheless. I wanted to call other family members and friends, but Kyle wanted to enjoy our dinner and call them later. I begrudgingly agreed, although I was too happy to be too upset with him! Throughout dinner, I kept telling Kyle how happy I was, how perfect the proposal was, and how I was so excited to spend the rest of my life with him. I didn’t think it could get any better! After dinner, he suggested we go meet Amy for some celebratory drinks. He wouldn’t tell me where we were going, but I was too happy to argue with him.

As soon as he told the taxi driver the address of our destination, I knew exactly where he was taking me – to Citizen Bar, where we first met! I spent the taxi ride trying to call my family and friends, but Kyle kept telling me I would be able to call them when we arrived at our destination.

I walked through the door to Citizen Bar to the biggest surprise of the day – all of our family members and a few very close friends waiting to celebrate with us! I was completely surprised and very emotional. I felt so incredibly grateful to all of our family and friends for coming to Chicago from Dallas, Houston, Indiana, Pittsburgh, North Carolina, and Philadelphia. I think I said “I can’t believe you’re here!” a million times that night. We had such a perfect weekend celebrating with all of our favorite people – I didn’t want it to end!



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I am inquisitive, observant, skeptical, and perceptive. I usually ruin my own surprises because I have trouble “going with the flow”. This time was different – Kyle planned the perfect weekend, leaving no stone unturned, and caught me completely by surprise. I am so sure that Kyle is perfect for me, and I cannot wait to spend the rest of my life with him!

Special Thanks

Paparazzi Proposals