Hilda and Roy

How We Met

We both work in Higher Education. He is a coach I work in administration. 5 years ago, we were working at the same University. One of his basketball players ended up in my office needing my help. One thing led to another and we met at one of his basketball games. Soon after he invited me to dinner to talk about “work” – mind you, the place we went to was one Chicago’s new trendy restaurants – you know the ones with dim lighting, perfect decor, and fancy drinks – yea right, this was NOT a “work” dinner! I was not mad about it. He had a game. There was undeniable chemistry and it was so easy to talk to one another. So, of course, the conversation went from work to personal. I told him that day that I was not one of those girls that only dreamed about getting married, that I wanted to have a successful career and that I didn’t need love or a family of my own to be happy. He didn’t judge me or question me.

It took a year and a half for us to become officially girlfriend and boyfriend – I was VERY resistant to letting true love do its thing. After many dates that we labeled as non-dates and some very awkward “Let’s define the relationship” conversations, we finally came back together. He drove a few hours to meet me and had with him an eleven-page letter. We were on this river walk. He asked me to allow him to read it to me and do not say anything until he was done. In the letter, he told me that he really liked me and wanted to give this a real try, no more non-date dates. After he was done reading, a group of young boys riding their bikes came right by where we were sitting. One of them stopped right in front of us, looked directly at us and said to my then soon-to-be-boyfriend, “You love her, you are going to marry her!” and rode away on his bike. We looked at each other in shock about what had just happened and just smiled at each other. We took that as a sign that we should give our relationship a real try. We walked away that day committed to giving true love a chance.

How They Asked

Three and a half years after that, my boyfriend wrote another letter. This time to my parents. They speak different languages and he needed to ask for their blessing to propose. He got the letter translated and drove six hours to go see them. Not only had he found the way to my heart, but he had also found a way to communicate and connect to the people most important to me.

He had told me to get ready for our Christmas date – a tradition we loved – time together, just the two of us, before the hustle and bustle of the holidays with family, friends and work commitments. We took off on our date. The first stop was a restaurant in the Art Institute of Chicago for lunch. Lunch started pretty normally but then the conversation turned more serious and personal – something like that first dinner. We reflected on the year, dreamed about our future and I told him at that lunch that I was the happiest I had ever been. I felt grateful, whole and at peace. Life was so good!

Engagement Proposal Ideas in Chicago, IL

He had drinks and dessert planned at stop number two, across the street at another restaurant. We left our lunch location and took the Nichols Bridgeway that connects the Art Institute to Millenium Park. While walking he slowed down and said, “I love this view of the city, it brings back so many memories” – a view we had seen many times, on walks and while running errands. He reached in his coat’s pocket, got down on one knee and told me that it was at that very first dinner five years ago that he knew he wanted to marry me, that he was glad we had found our way to each other, allowed true love to show up and that today is the city we both loved and that had brought us together, he wanted to ask me something – “Will you marry me?”

Wedding Proposal Ideas in Chicago, IL

Proposal Ideas Chicago, IL

Special Thanks

Zach Caddy
 | Photographer