Gabby and Dennis met at a mutual friend's house before going to a concert at Concord Music Hall in Chicago's Wicker Park neighborhood. Originally, Gabby was not even planning to go to the concert, as she had other plans. As fate would have it, those plans fell through and she was invited to go over to her friend’s house to meet up with everyone and go to the show together. As the gathering went on, Gabby and Dennis finally chatted. This is when Gabby learned of his name :) and his work moonlighting as an adjunct lecturer at the University of Illinois-Chicago – the school Gabby was currently attending as a nursing student. Gabby has since divulged that it was Dennis’ work in teaching that initially drew her interest. Eventually everyone headed to the show where they talked for most of the time (mostly Gabby). There may even have even been some dancing. When the show was over and people were going home, the two of them still wanted to keep talking so they made their way to Kingston Mines for more drinks and dancing. As the night was coming to a close and they finally headed their separate ways both couldn’t help but have an inkling suspicion that this was meant for something greater…
It was Memorial Day and Gabby had been bugging me to take her driving. Gabby has been living in Chicago for 10 years now without a car and was in dire need to practice her Tokyo drifting skills. So we went out driving around the neighborhood to help her get some practice. Little did she know that I had been holding onto the ring for some time now and was waiting for the right time – this seemed like it! I had been thinking about where I wanted to pop the question for some time now and had the perfect place picked out. There was this beautiful bird sanctuary right off Lake Michigan in the Montrose Harbor where my buddy docked his boat for the summer. This was the place. This was the time. I casually dropped the idea of checking out the bird sanctuary, explaining that I had never been before and it would be a good spot to take a break from driving and chill for a minute. After some positive encouragement that she was ready to take the car on Lake Shore Drive, I directed her north on LSD to the Montrose exit that led to the reserve. With the ring in my back pocket and my heart-rate slightly elevated, I walked through the reserve and around the lake with Gabby. As we got to the outer point of the lakefront path with the waves splashing against the concrete and the skyline to our backs, I asked the question. Now I don’t remember exactly what I said but she got the gist. Let the light crying, laughing, and selfies commence!