A proposal is a pivotal moment in any relationship, and we wanted to share our proposal story to provide some insight into how God timed this moment for our relationship.

How and when did you decide you wanted to propose to Jenn?

Gordon: After our Door County trip in early October 2022, I pondered what the Holy Spirit had revealed to me for awhile and it wasn’t until after I took a trip to Austin towards the end of October 2022 with my sister Rosalind that I had the time to sort out both what the Holy Spirit revealed, and also my own feelings and fears regarding committing to marriage and taking next steps. After the Austin trip, I began to feel a stronger conviction that the timing was critical, so I reached out to Jenn’s parents the second week of November 2022 to ask for their blessing to propose. Thankfully we had a chance to meet each other earlier in September when they came to visit Chicago. After talking to Jenn’s parents, I told both of my sisters that I wanted to propose, and both Grace and Rosalind were incredibly supportive in helping me shop for rings, including covertly participating in a jewelry making party with Jenn to get a sense of her style and get the all important ring size! Throughout November and December Rosalind and I tossed a few ideas back and forth, and she was instrumental in helping me come up with and executing the final plan. :)

How and when did the proposal go down?

Jenn: Well, Gordon and I have had pretty open communication, so I had asked him to let me know a week or so ahead of time so that I could be prepared to dress up everytime I saw him. That way we would be sure to have decent engagement photos, lol.

Anyways, his sister, Rosalind, had asked me about a month ahead of time if I wanted to do something with their family on New Year’s, and since I was spending Christmas in New Mexico with my family, I thought that would be a great idea. A few days before New Year’s though she said that after spending a lot of time with family on their Christmas retreat, she had decided she didn’t want to do a super involved family celebration that day and would rather just spend time one-on-one and go to afternoon tea at The Drake. This was an invitation I couldn’t refuse since I have literally had experiencing afternoon tea at The Drake on my bucket list for years!

On New Year’s Day, I was coming back from leading a weekend youth retreat with my church. Fortunately, we got back a bit earlier than expected. It gave me the chance to drop off half of my stuff at my house, grab a quick shower, and head into Chicago for afternoon tea. When I got there, Rosalind met me at the door and we walked through the lobby to the Palm Court which was breathtaking! Honestly I was so excited I apparently didn’t see Cheryl, Eric, and Gordon hiding in the stairwell behind me when I turned around to check our coats, XD!

Gordon: It’s hard for me to tell lies, so when Jenn asked me to let her know which week the proposal would go down, I simply told her “the first week of the New Year” knowing full well it would be exactly on 1/1/2023. I definitely didn’t lie! :) Rosalind and I had to find a way to keep things a surprise of course, so in addition to making Jenn think she was only meeting with Rosalind at The Drake, we decided to come up with a specials menu that contained some plausible holiday specialty teas, and put some experiences in there also including a “Proposal Special” towards the end of the menu. The idea was to surprise Jenn with the ring presentation and pop the question as soon as she finished reading the menu, and I needed Rosalind to cue me for the exact right timing while coordinating with the waiter and manager at Palm Court. While Cheryl, Eric, and I were waiting in the lobby stairwell, I did some practice poses with the ring to get myself ready.

Jenn: We were seated at this beautiful spot with a great view of the Palm fountain and the harpist. Rosalind said she was going to go use the restroom and as she got up a waiter came by and handed me a menu with their “holiday specialties”. I started reading it and as I got to the end, I kinda jumped because my name was there under the “Proposal Special” with a note from Gordon. I was a little overwhelmed in the moment and then I heard Gordon’s voice coming behind me and I saw him walk around the corner and kneel down.

Gordon: When Rosalind cued me, I walked into Palm Court and waited behind Jenn. As soon as I saw her body shake up in surprise, I knew it was time to approach her, so I walked up around her and as I got in front of her, I said “So I heard someone ordered the proposal special. Well here I am, will you marry me?” I was looking at her face the whole time, and the look of surprise and happiness on her face as she said “Yes!” was absolutely priceless. By this time, we were hugging and kissing, and the other patrons at Palm Court had caught on to what was going on, and erupted in applause, it was truly a magical moment!

Gordon, were you nervous at all? What was your backup plan?

Gordon: I really appreciate that our relationship has very open communication, so honestly I wasn’t really nervous about Jenn saying no as she has consistently made her feelings about me very clear. :) I was far more nervous that something would go wrong logistically with the plan or that Jenn would possibly see me, Eric or Cheryl in the lobby of The Drake, but we had a plan B. If we did get caught, we would just have made an excuse as to why we were there and mentioned that we heard Rosalind and Jenn were doing afternoon tea there and instead go back to Rosalind's house to surprise her rather than at Palm Court. I had prepared two lego block plates separated into two layers that spelled out “Will You Marry Me?” with legos, and the plates were hidden away inside an emptied chocolate tin, as well as a lego flower in a vase. We left all this on Rosalind’s kitchen island and the backup plan was to go hang out at Rosalind’s house after afternoon tea and present the chocolate tin as a holiday gift to Jenn, and she would be surprised with the words as soon as she opened the chocolate tin. Since plan A worked, we ended up using plan B as a second surprise. We video called Jenn’s parents from Rosalind’s house after afternoon tea to share the good news of our engagement, and while we were on the video call, we presented the chocolate tin and Jenn opened it in front of her parents live on the video call, so her parents got to share in the surprise!