Matt and I have talked about marriage since early on in our relationship, but when I accidentally saw a photo of a ring box on Matt’s phone is when I could finally picture everything falling into place. This is the story of how Matt was still able to trick me and give us the proposal we always dreamed of.
As told by Kayla –
We had plans for a lunch cruise on Lake Michigan to celebrate my recent work promotion. A week before, I was taking a picture with Matt’s phone. When I went to send it to myself I saw there was a photo of a little velvet ring box with a gold embroidered “K.” Naturally I got so excited and ordered a new dress and scheduled a manicure all while Matt was realizing (and panicking) that I must have seen the picture of the box. All week I was so excited and Matt was coming up with a plan. Fast forward to the day of the cruise. We had a nice morning together making breakfast at home and watching The Office, our favorite. On the cruise we had great conversation over a delicious lunch and drinks. It was the best time, and while I didn’t think he was going to propose on the boat, I was on edge all day wondering when and if it was going to happen. We had no set plan after the cruise except to go around the city to our favorite rooftop bars. I started to get worried when every place we tried to go to was either too crowded or closed for a private event. We ended up on a random patio a bit far from home as it started to get late. That’s when Matt got really excited and told me he had a surprise for me, something small for my promotion. As he reached into his coat pocket, my heart sank as I realized that I had been wrong about the whole day. When he pulled the ring box out of his pocket and handed it to me I didn’t know what to think. I opened the box to find a beautiful necklace and looked up to Matt beaming. I felt so guilty that I was upset over something that I had worked up in my head. He could see how upset I was even while trying to mask it. I was ready to call it a night when he told me he had one more place he wanted to show me. Not even remotely thinking that there was a chance of a proposal, I reluctantly agreed. The drive to the next spot was a blur. Matt escorted me into a beautiful, vacant park that I didn’t realize at the time had been rented out for the two of us. The sun was hitting the trees making the whole pond feel golden. He walked me over to an opening by the water, turned me to face him and grabbed both of my hands. “Kayla…” I started sobbing and laughing on the spot. He got me so good and I couldn’t believe all of moments leading up to this one were to throw me off. I also couldn’t believe what a sweet proposal he came up with in the most beautiful park that I didn’t know existed. The night ended with a surprise party on our apartment rooftop with family and friends that flew into town for the occasion. We laughed, cried and celebrated the love that we’ve shared since day one. And after all of that, I got to keep the necklace too.
As told by Matt –
Part 1 | What I planned: Throughout the year prior to the engagement I slowly gathered details on what I thought would be Kayla’s dream proposal. After having many conversations with Kayla’s sister Heather, creeping on Kayla’s Pinterest and talking with my mom and sister Elizabeth, I finally began to get a better idea of how I wanted to ask. My main goal was to have Kayla not expect it, but also do something out of the ordinary that we would always remember. Something Kayla and I always talked about was getting on a boat on Lake Michigan to see the Chicago skyline. I had always planned to propose in July, but it worked in my favor when Kayla was promoted at work around that time. I decided to tell Kayla I wanted to take her on a lunch cruise to celebrate her promotion. Allowing Kayla to know one aspect of the day ensured that we would be dressed up without giving anything away. I wanted to propose somewhere seclusive and I made it a goal to bring her somewhere she had never been. After spending hours researching, I found Alfred Caldwell Lily Pool, and since Kayla had never mentioned it to me, I knew it was the perfect spot. When I called the park, they told me I could rent the park for just us two. With the lunch planned in the afternoon and the park rented for just before sunset, I needed to plan things for the in between to throw her off. London House rooftop bar has our favorite view of the city, so I knew I wanted to take her there. Then later I planned to take her to J Parker, a rooftop that neither of us has been to that was close to the park. Now that most of the day was planned, I needed Heather’s help with one of the most important pieces, organizing our family and close friends flying into town for the day to surprise Kayla after the proposal. After many texts and phone calls, we confirmed the plan with a group that could make it that day. The easiest part of the plan was catering choices, Green Street Smoked Meats BBQ and Domino’s pizza. After months of planning, everything was set and going smoothly. I was finishing the final touches by getting a customized ring box to propose with (thanks to Heather sending me pictures from Kayla’s Pinterest, yet again). I had it shipped to my office to make sure Kayla wouldn’t see it. The ring was hidden in my tackle box, the one place she didn’t look (and trust me, she looked, I could tell). About one week before the proposal, Kayla was using my phone to take a picture for her wellness account. I realized too late that the photo I had sent to Heather of the ring box was still in my photo gallery. When I went to bed that night around midnight, Kayla was still awake despite normally falling asleep much earlier. When I asked what she was still doing awake, she said “I’m so excited.” I knew.
Part 2 | What actually happened: Something I didn’t think of until getting ready the morning of the proposal was how I would hide the ring box in my jacket. This was the first of many hiccups that would happen that day. I went ahead and put it in my jacket pocket praying Kayla wouldn’t notice the slight bump from the box. In the late morning, the first thing I had lined up for us was the boat ride and lunch out on Lake Michigan. We took an Uber to the harbor where we thought the boat would pick us up. It turns out, we got dropped off on the wrong side of the pier and we had to walk against crazy winds all the way around to find the right location. Kayla did not enjoy the wind blowing in her face which was messing up her hair. Once we found the correct location, we got in line and showed our tickets so we could board. When we were greeted by the hostess, she asked us what the occasion was. I choked up and said “Oh, nothing” completely forgetting that I told Kayla that this was for her work promotion. Blew that one… Once we were directed to our table, we sat down and were greeted by our server who took our orders for drinks and our lunch. The service was phenomenal and the drinks they made were unmatched. After we ate our food, we decided to go upstairs to get pictures of the wonderful views. After about 20 minutes, we took enough photos to fill an album (thanks, Kayla). When we came back down, I noticed that our table had rose petals all over it. I instantly became nervous that the staff was going to blow any kind of cover I had left of the day. I did put a note on the reservation that the lunch was for a proposal and proceeded to put in all caps “DO NOT SAY ANYTHING.” Kayla thought the petals were nice and didn’t think anything of it. Then, we went outside again to come back a second time only to find the rose petals rearranged into a heart. My heart dropped. As soon as we sat down, one of the managers came over and said, “Happy Anniversary! How many years have you been married?” This was always an opportunity for Kayla to throw a kinda kidding, kinda not joke that we weren’t even engaged yet. Without fail, she told the manager exactly that. This actually broke the ice and we immediately all laughed and forgot about the petals all together. After the boat, I had planned for us to kill some time before the Lily Pool by visiting our favorite view of the city, which is London House. We would then go to J Parker which is a walkable distance to the Alfred Caldwell Lily Pool. Once we got to London House, we noticed the line wrapped out of the building and went outside. We did not have time to wait for this line. I made the decision to go a few blocks over to Raised which is also a great rooftop bar, it’s just not as nearly high up. This was better because Kayla and I got a table and were able to actually talk without screaming over the noise of a ton of people at London House. After getting drinks there for a couple of hours, I took a few trips to the bathroom to check on the ring and to gain some composure since most of the day was filled with spontaneous changes. Once we left Raised, we then took an Uber over to J Parker. Once we got there, I noticed groups of people being turned away. This wasn’t a good sign. The staff told us there was a private event and that no one was allowed up. Another part of the plan in the mud… This was where a very important step in the plan, so I improvised. I saw another bar next door that looked nice and asked Kayla if she wanted to go there till we “figured out what we wanted to do next.” The key at this point was to act like there was no actual plan and that we would just go with the flow like we usually do. Once we sat down, I proceeded to give her necklace inside the ring box that she had seen on my phone that I had picked out the day prior. You may ask why I did this? I needed to throw her off. Based on her nails being done, wearing a new dress and how she was acting the whole day, I knew she knew today was the day. By giving her a necklace inside the box she saw, the thought of engagement would entirely leave her head. It worked. She opened the box and was so happy that I got her a necklace. I watched her brain piece together that it was the box she saw on my phone and she started to become sad. As happy as I was that my plan worked, I was sad to see her so upset because she played up the day so much in her head. For the next part to work, I needed to get the box back from her so I could put the actual engagement ring into it and actually propose at the Lily Pool. After asking for the box back, Kayla declined, having already put it away in her purse. I asked again, Kayla declined again. One more time… I asked and she finally handed over the box. As we wrapped up, I told Kayla I needed to go to the bathroom. This was an opportunity for me to put the ring into the box and for Kayla to gain some composure since she was on the brink of tears. Once I got back, Kayla proceeded to tell me how upset she was and that “I should be careful giving a ring box with a necklace in it to a girl that is expecting a proposal.” I agreed and apologized. She was so happy about the necklace but also so upset that it wasn’t a ring. She felt bad that she felt sad, which is so Kayla. My plan from here was to walk to the Lily Pool, but Kayla seemed so distraught. I hated seeing her like that so I flagged down a taxi driver that was driving by, this would make the trip over much quicker. When we got into the taxi, I told Kayla that there was one more surprise. I told her it was a “speak easy” to throw her off. She did NOT seem about it. I wouldn’t have either… When we pulled up to the entrance, my contact that worked for the park was at the entrance. We had a plan for me to say “Are you guys open?” and she would say “Yes, come on in!” We did just that and it was just us in the park. Everything on this part was going according to plan. As we walked around, I wanted to get to the planned spot where our photographer, Zoe, was hiding so she could take our photos. But, I didn’t want to seem unnatural. I began to ask Kayla questions about if she has ever heard of this Lily Pool or if she ever went in and she shortly replied “no” to all of my questions. As we walked, we finally got to the spot I envisioned. I then proceeded to get on one knee to propose. Kayla then realized I was getting out the same exact box as before. I opened it and there was her engagement ring. She immediately bursted into tears and fell onto my knee in disbelief. It’s the exact response I wanted and dreamt of. This moment and the pictures taken captured everything perfectly. There was one more thing planned for us. It happened to be the most important part of the day. After getting yet another thousand photos, we were heading back to our apartment. Kayla had an idea that our family and friends were going to be there, but all of the twists and turns in the day made everything unpredictable for her. When we pulled up, she began to ask me more questions. I told her repeatedly not to ask anymore questions and that she would see in a bit. I asked her to close her eyes and we headed up into the elevator. We got to the top floor and I walked her outside onto the rooftop of our apartment where everyone was hiding. She opened her eyes to see our wonderful family and friends that made the long trip out to celebrate with us. This was the perfect way to cap off the wonderful day and night we had.
July 27, 2019 | Photos by Zoe Ekonomou
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