Coniah and Gboyega

How We Met

When I was in college, I worked at a retail store and made a lifelong friend. She left our location to go to medical school and decided to have a housewarming party in her new apartment. While there, I met a few of her nice male friends from college. I instantly thought one of the guys was attractive. Throughout the night, we all had stimulating conversations about love, life, and marriage. Incidentally, the conversation landed on the prospect of a prenuptial agreement. I tend to play the antagonizer in debates of this sort but this time I had met my match. My future fiance and I stole the evening in a riveting debate about the morality of the current marriage system in America. His sound judgment and apparent knowledge about how he would handle his future situation intrigued me. Although we did not exchange numbers that evening, another opportunity arose six months later. He was organizing a plot during the Foxfield races in Charlottesville, VA and my friend invited me. I had to reach out to him for logistics so he finally had my number. The day of the event, he was incredibly flirty and even suggested that he be my “boyfriend” just for the day. This is how I knew that the feeling was mutual. We left with no real plan in place and I was sort of dating someone at the time but was interested in him as a prospect. When I returned home, I sent him a photo of him at Foxfields and he initiated a flirty conversation via text. I never responded. A year later, my same friend had a birthday party. To my surprise, he was there and all of the flirty vibes came back instantly. Tired of the cat and mouse game, I immediately made my position known. I quickly said, “the last time I saw you, I was dating someone. Now I’m not.” We danced the whole night together and have been inseparable ever since. Here we are nearly four years later. We have moved to Chicago, traveled together, and recently got engaged. Our debates are still as exciting and thought-provoking as they were the day we met.

Engagement Proposal Ideas in Waldorf Astoria Chicago

How He Asked

For background, my boyfriend and I moved to Chicago in December of 2015 immediately after Christmas. It was an unspoken assumption that we would be engaged sometime shortly after (my father even said, “just get married now.”) After 11 months in the new city, another couple that we were friends with asked when he was planning to propose right in front of me. He quickly responded Q4-2016/Q1-2017. We were nearing the end of Q4! The holidays came and went and then Valentine’s Day came. I decided that this occasion would be about him, so I made the dinner plans and purchased the gifts with no expectation from him. Realizing that I had stolen the holiday, he gave me a spa package to Red Door and booked the appointment for the following Thursday, which was the day he would return from a work trip. I immediately remembered a conversation where I stated that no woman wants a proposal without a fresh manicure. He was trying to cover his bases. So I accepted the gift while thinking to myself that Thursday is the day.

Coniah's Proposal in Waldorf Astoria Chicago

I go to work that morning prepared. I stressed my colleagues out all day about what seemed imminent. I head to my appointment and even the spa staff hint that this treatment is more than just a Valentines Day package. I rush home with excitement and when he arrives, he jumps in bed and goes to sleep after asking how my appointment turned out. I was wrong! We had dinner plans scheduled for the next day which is our weekly ritual. He texted me and told me that he booked the reservation through his credit card concierge and that they told him about an art gallery event that was nearby. He then said, try and get home early enough so that we can be on time (this was cryptic for don’t make us late like usual). I rushed home and quickly got myself together so that we could make the art event. We pulled up to the Waldorf Astoria hotel and I said, “this is a fancy art event.” He agreed and we both walked in not knowing what to expect (or so I thought). We take the elevator up to the 5th floor to the banquet rooms and I noticed a crowd of people. I just assumed that they were there for the same event. We walk past the crowd to a room in the corner and there is a photo gallery on display. I instantly realize the photos are of us and then I freeze. He ushers me throughout the room where each table displays a different phase in our relationship as a photographer captures the moment. Then he stops and says to me, “You know what I’m about to do right?” We walk onto the balcony and he asks if I will be his wife. I’m still in shock but I say Yes! quickly.

Proposal Ideas Waldorf Astoria Chicago

Where to Propose in Waldorf Astoria Chicago

The photographer then takes us to the courtyard to snap more photos and once we finish we head back to the room which has now been transformed into a private candlelit dinner for two. There was a menu displayed that said congratulations Coniah & Gboyega and the staff served my favorite wine. Literally, every element has been thoroughly planned.

We get ready to exit and instead of going back to the lobby, he takes me to a suite that he reserved for the evening. There was a photo storybook of our lives on the living room table with a letter signed, Your Future Husband.

Special Thanks

Jessica Wielgot
Photographer