Kelly and I met junior year of high school before a Cor Jesu homecoming dance in 2012. We had been set up with different people, but our group had such a great time! We quickly became friends. We saw each other often throughout the rest of high school: at parties, school dances, as ambassadors for our high schools, during our indoor soccer league, and even studying together one-on-one at the Kirkwood library (admittedly our first kiss). I still remember my mom insisting on getting pictures of just Kelly and me at many of those dances. Sometimes moms just know. After high school, we went to different colleges: Kelly to Mizzou and me to Notre Dame. During the summer of 2015, she had a babysitting job down in Oakville near my parents’ house. Every time she was nearby, she’d text me, and we started hanging out more and more. It was a really fun summer. What started as a few friendly meetups turned into a full-blown relationship. We spent our sophomore year of college visiting each other in Columbia and South Bend, making it work despite the distance. Eventually life pulled us in different directions, and we lost touch for a while. We would still randomly run into each other whenever we were both back home in St. Louis. After graduation, Kelly moved to Denver, and I moved to Madison, WI. Even though we were living totally separate lives, I always had this gut feeling that we were compatible. I remember telling a buddy that if Kelly and I ever reconnected as adults, it would go the distance.
Time and place are everything. Fast-forward to the fall of 2023. For the first time since high school, Kelly and I were both single and living in St. Louis. My mom ran into Kelly’s mom at the Gateway 180 charity gala, where they caught up. They talked about how we should get back together, as moms do, and they insisted that I reach out to Kelly. So I texted her. I spent a while figuring out what to say, and I eventually decided to ask her to "network" since we were both working on our MBAs. Smooth right? She knew better. We met at Hartford Coffee to talk grad school, but we ended up talking about everything BUT grad school for hours. As we were leaving, I awkwardly asked if she’d want to hang out again, and she said yes. Our first official date as adults was at Seamus McDaniel’s in Dogtown. Our waitress told us that it looked like we knew each other, but she could definitely tell it was a first date. She was spot on. She said we made a really cute couple. I’ll admit I was a little nervous because I felt so strongly for Kelly so quickly. That turned into another date, and another. By the beginning of 2024, we were officially back together. Kelly had just bought a house in Shaw; I had one in Southampton. We spent a lot of time in South City, rediscovering St. Louis and each other. Before we had reconnected, Kelly had already accepted a job up in Chicago following an internship the summer before. She was scheduled to start in July 2024, and I decided to move with her. She got a place in Old Town, and I moved in across the street. We grew even closer exploring our new city, talking about our future, and making plans. I knew she was the one well before that.
When we were back home for Thanksgiving in the fall of 2024, I met up with Kelly's dad to talk about how I wanted to ask Kelly to marry me. I asked for his blessing, and we had a great conversation. A couple days later, I picked out a ring. Right before Christmas, I planned a date. I picked up Kelly and headed to Tower Grove Park to grab a drink at a Christmas pop-up bar in the Piper Palm House. When we got there, I was so nervous that I dropped the ring box getting out of the car. Luckily Kelly didn't see. We walked by the spot, I got down on one knee, and she said "Yes"! The rest is history.