Matt: I wanted to propose on July 20th after our first date but decided to wait. Finally, after 5 months I decided it was time to propose. Caley loves the city of Chicago, specifically the picturesque skyline, so I decided to center the proposal around that. After booking a restaurant every day for a week straight to give myself flexibility and that advantage of the element of surprise, I decided Friday, December 22nd was best. I took her to Milton Lee Olive Park with great views of the city, where I had Ben set up candles, and there I proposed. After she said YES! We went to dinner at Cite restaurant at the top of a high rise building with great views of the city. It was a night I will never forget. Caley: I had a hunch that a proposal was coming soon, but I did not suspect that it was going to happen that night. It was my last day of school before Christmas break, and I was busying myself in the classroom trying to get a few things taken care of, making me (almost) late for our dinner plans. When I finally left school, I headed to Matt and we started walking towards the lake. Matt told me we were going to a new restaurant at Navy Pier, so I kept busily chatting as we walked. Before long we turned down the path of a favorite park where we had run and walked together before. This park has gorgeous views of the lake and skyline, and it’s quickly become a favorite spot of mine. Matt said we had some time to kill so we could take a walk until dinner. As we walked I began to notice that there were candles set up at the lookout point over the lake, and when I looked over at Matt, I realized what was happening. :) He walked me to the center of the lookout point, got down on one knee, and with the beautiful Chicago skyline in the background, he proposed! I could hardly say "Yes!" fast enough! I was already feeling on top of the world, but then we went to a romantic dinner at a rooftop restaurant overlooking the city and lake. It was a night I will always remember.