Caitlin and Ryan

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How We Met: Caitlin and I met in 2008 when I started to work for the same company as her in Pennsylvania. During my 2 years at that company, Caitlin and I only exchanged a handful words. I then moved away to take another job and never thought I would see Caitlin again. The last thing I thought was that I was moving away from the person I would spend the rest of my life with. As it would turn out, in 2010, we both got job offers (through a previous boss) to move to Chicago for a new opportunity. Chicago was going to be a big step in both our personal and professional lives. We both felt a little comfort that there would be at least one other person we knew there to help ease the transition. While in Chicago, we got to know each other better, both in the office and out. I had always thought Caitlin was a great person, but not until I got to know her better in Chicago did I realize what an amazing person she was. We started dating shortly thereafter and fell in love with each other and the city of Chicago.

Proposal Planning: I had been planning this proposal for months and was hoping that everything would work out smoothly. As Caitlin (and Megan from Gray Photography) will attest, I am an extremely organized person who likes to make sure everything will work out exactly as planned. As it happened, after I had everything booked, Caitlin and I found out that we would be transferring to Texas for our jobs that summer. Before the move, I knew that we would have so much to do including house hunting and I was extremely worried that these would conflict with the proposal. Luckily, it did not and I was able to propose in the city where we fell in love.

On the day of, it was raining all day and I knew this was going to cause issues with the entire idea. Thankfully, Megan and I were able to secretly communicate via text as she reassured me that she had a backup plan. As I previously said, anything outside of the plan is stressful for me, and I spent the entire day wondering whether it would all work out and Caitlin would be as surprised as I had hoped. Just hours before we were set to leave, the rain cleared and I got the text that everything was in place!

How He Proposed (Caitlin’s view): It was a Friday, which is normally one of my favorite days of the week, but I was having a bad day. I knew Ryan had a fancy dinner planned for us but I was partly considering suggesting that we cancel and just stay in for the night. He thought getting dressed up and going out would make me feel better. We got in a cab and I realized we were running extremely early for the reservation. Ryan suggested that we could go take some pictures near a gazebo across from the restaurant. I typically love pictures but as I stepped out of the cab into the humidity, I boldly stated that I would rather just go inside for a drink. Ryan quickly responded “WE ARE GOING TO TAKE SOME PICTURES.” Ryan’s demanding tone was out of character so I thought something seemed suspicious, I just didn’t know what. As we crossed the street and started walking towards the center of the gazebo, everything happened so quickly. Ryan was pulling something out of his pocket and dropping to one knee. I felt like the surrounding people on the streets knew what was happening before I even did.

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After Ryan’s romantic proposal, I happened to look over his shoulder and realize someone was taking my picture but I was too much in shock to react. The clapping and cheering from the bystanders around us made me realize I had yet to respond…of course I said yes and realized the most beautiful ring was being put on my hand! After a few hugs and kisses, Ryan announced that he had one more surprise. It then clicked that he must have hired a photographer to take pictures of us. We start walking towards the photographer but then slightly turned and headed towards a woman sitting on a park bench. As we got closer, the woman looked up and I stopped in shock! It was one of my best friends from Pennsylvania!

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I can’t even describe how confused and surprised I was! Ryan had flown her out to Chicago so I would be able to share the special evening and weekend with a childhood friend. She handed me a dozen beautiful bright pink roses Ryan had her pick up for me. After the craziness settled, it was brought up that we would start our photo shoot with Corlis and Megan of Gray Photography. I couldn’t ask for better photographers. Even though I was just meeting them, I felt like I already knew them especially because of how friendly they were. I realized how much fun this shoot would be since we had such an important event to celebrate and the amazing scenery of the Chicago skyline and the lakefront.

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As the pictures wrapped up, Ryan said we would be headed to a surprise dinner (not the original place he had told me!). As we pulled up, I realized that we were at a place I had been dying to go to for lobster tail. After we had our champagne toast, I continued to feel shocked at how my horrible day turned into one I will never forget. We had a fabulous dinner and I couldn’t ask for a more special proposal. Now comes the wedding planning!

Photos by Gray Photography