James proposed to me on November 23, 2019 around 10:30 pm, exactly 5 years to the day we began dating. He surprised me by renting out the cupola on the rooftop of the LondonHouse in Chicago. It was a very romantic and intimate moment. James put so much thought into every detail, and it turned out more magical than I ever could have hoped for.
James arranged to have a carpet of rose petals, a bottle of Dom Pérignon champagne, and chocolate covered strawberries waiting for me! The second I saw the rose petals I knew what was about to happen, and I became very emotional.
The Surprise…
A couple of weeks prior to our 5th anniversary of dating, James casually suggested a weekend trip to Chicago, to celebrate our milestone and to see the Giants play the Bears at Soldier Field. James is not much of a planner, so it almost immediately occurred to me that he might use it as an opportunity to propose. He even joked that he was going ask me on the field at the Giants game, since he knew I would hate that haha (I had expressed to him that I wanted our engagement to be an intimate moment). It turns out I hate surprises. Leading up to the trip I became very nervous. Should I get a new dress? Do I need to get my nails done? I hated not being in control of such an important moment. James even caught me snooping in his phone for clues. I found no sign that he had any plans to propose and broke down in tears when he asked me about it. He was so sweet and reassured me that I shouldn't worry about it. Ultimately, I made up my mind to have a wonderful time no matter what happened that weekend. ps. buy the new dress, get your nails done!
The Trip…
We planned to leave Madison WI early Friday, but discovered we had a nail in one of our tires. James handled this curveball so well. He took the car to the shop, walked home in the snow, and then took me to brunch on State Street while we waited. Then we were on our way! We checked into our favorite hotel in Chicago, the LondonHouse, where we had stayed for St. Patrick's Day earlier that year (Check out our trip: https://meghanotoole.com/st-patricks-day-in-chicago-2019/).
Day one…
James took me to Millennium Park to go ice skating and watch the Christmas tree lighting. Skating around in the cold to the first Christmas music of the season was pure magic.
Day two…
On the morning of our anniversary James took me to the Chicago Planetarium. We later learned that my Grandfather proposed to my Grandmother in nearly this exact spot in front of the planetarium years ago! (It occurred to me that is might be a good spot for a proposal). The visit to the Planetarium held a special significance to us, because for our first date James took me to see Interstellar at the movie theater near Notre Dame. It is now his all time favorite movie... coincidence? I think not!
After walking all over Chicago all day our final stop was the top of Willis Tower (formerly the Sears Tower) to watch the sunset. (It also occurred to me that this would be an excellent place for a proposal).
On the way back to the hotel from the top of Willis Tower we got caught in the Christmas parade.
Luckily our room had an amazing view of the fireworks on the river and the parade. We sat together on the window sill and watched it all go by. It was very cozy and romantic!
Unfortunately, we lost track of time while watching the parade, and I began to be short on time to get ready for our 8 pm dinner reservations. I begged James to call the restaurant and move the reservation, but he refused. I was upset because I wanted to get a few pictures of us all dressed up before went to dinner, and I worried that we wouldn't remember to take them after dinner. James assured me that we would absolutely take better pictures after dinner (he really wasn't kidding). We grabbed this single picture on my iPhone in the hotel lobby right before we left for dinner at Prosecco.
We added white truffle to every thing!
The Proposal…
After dinner James brought me back to the hotel, and told me that he had made reservations for us on the roof at 10pm as a surprise. This explained why he refused to move our dinner reservations! We headed up to the rooftop bar, and James gave the host his name. The host said, "Right this way Mr. O'Toole" and led us to another elevator that took us straight to the rooftop cupola. As soon as I saw the rose petals I knew what was happening.
Finally, after all the pictures and excitement we sat and enjoyed the fire together, sipped our champagne, and took it all in. The rooftop was all ours for an hour and we enjoyed every second of it.
