An elegant harbor cruise with a candlelit dinner for two would be an ideal romantic situation. However, she would know it was coming in an instant and I needed to utilize the element of surprise. And then I figured that I could double up my surprises because I was surprising my family in Chicago for Thanksgiving and they had no idea that I was coming. The perfect plan, or so I thought.
A few days before our trip out there Cailey and I were walking around the North Shore Mall and she was telling me about her day at work. She was joking about how all of her friends at work were saying that they thought I would propose in Chicago. Upon hearing that I was able to produce my most fake laugh ever and kind of shrug off the whole idea. She responded to them with, “I know PJ and he wouldn’t do it then, he can’t even afford a ring yet.” That made me feel a little safer because I don’t think her radar would be completely on.
This brings us to November 21st . Because of work conflicts Cailey actually flew to Chicago on an earlier flight than me, and she met up with my Aunt Peggy, who was the only person who knew we were coming in, and spent the day with her and my cousins. I was coming in at about 7:00 that evening. Throughout the course of the day I had to check my inside pocket on my coat at least 20 times to make sure the ring was in there and that I hadn’t fallen out. Now it was crunch time. I took the train from the airport in Chicago to a station about three blocks from my Aunt’s house. Cailey was meeting me there and we were going to go downtown and walk around the city for a while. My heart was pounding from then on.
We decided to head to Navy Pier in Chicago, which is probably the city’s most prominent tourist attraction. Unfortunately the weather was dismal. It was about 35 degrees out and raining. Not to mention that the city was living up to its nickname of the Windy City. The gusts were atrocious and it was all in all a crappy night. We went out to dinner at Bubba Gump Shrimp Co. and after dinner I was going to make my move. Navy Pier has the largest Ferris Wheel in the country. It takes seven minutes for it to make one rotation. I wanted to wait till we got to the peak of the ride and with the Chicago skyline in the background ask Cailey to marry me. Obviously the Ferris Wheel was closed due to the inclement weather. Cailey didn’t really care too much, but I truly was panicking. I had to do this tonight and I had to make it magical.
On to the impromptu plan B. We took a cab to Millennium Park, which is very similar to the Boston Gardens, to walk around in the crappy weather and attempt to enjoy the night. Millennium Park has an enormous statue of a Bean that reflects the entire city across the width of the structure. Cailey and I always made it a point to visit the Bean whenever we were in town. I was going to do it under the Bean! As we got out of the cab Cailey started to complain about the pain in her heal from a new pair of shoes she was wearing. She didn’t even want to stop at the Bean, she just wanted to sit on a bench and put on a few band-aids. The asshole in me came out and I said, “no, I need a new picture with you in the Bean because I want to make it the background on the desktop of my computer.” The cuteness of my comment convinced her to trudge along underneath the Bean. My mom must have been looking down on me because nobody else was there and I knew she didn’t want a big public display with the engagement. We’re under the Bean. I pulled her close and kissed her. I told her I loved her. I got down on one knee. She gives me the most shocked look I have ever seen. I pull out the ring… and I drop the box and watch it go flying about ten feet because of the horrendous winds.
I could have qualified for the Olympics in my sprint to go get that box. I was able to recover it and return to Cailey, albeit so of the surprise element had diminished. Again I got down on my knee and asked if she would marry me. I didn’t get the initial response that I imagined I would. She said, “Ah, Ah, Ah, ha-ha, YES.” She actually laughed at me when I proposed to her. It took her about ten minutes, but she eventually began balling her eyes out, which was my expected response from her. She called her parents and I called my father and they were thrilled for us.
I married my best friend and I could not imagine ever asking for anything else.
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