Reilly and Kristin met on a Colorado ski trip in 2021 through a mutual friend (groomsman Braydon Frazer). They quickly got to know each other over the weekend and over the course of the trip, as Reilly made an effort to spend time and talk more with Kristin. From offering to teach her how to snowboard, sitting next to her in the car, splitting food with her at restaurants, or staying up late after everyone else went to sleep to just to keep talking to each other, there seemed to be a connection between the two. After the ski trip, Reilly and Kristin kept in touch despite living in different cities. Just a few weeks later, Reilly made plans to come up from Houston to Dallas to celebrate his birthday with friends where Kristin also conveniently lived. Reilly and Kristin went on their first date while he was visiting. They dated long distance, taking turns commuting back and forth from Houston and Dallas, for over a year before Reilly moved up to Dallas where they continued dating.
Kristin & Reilly went on their first solo trip together to Chicago after one year of dating in May 2022 and loved the city! Ever since that first trip they dreamed of going back again. Fast forward to September 2024- Reilly had a minor procedure one morning and after recovering for a few hours he asked Kristin what their plans were for the weekend of October 24th. When Kristin said nothing, he said good because he had bought them flights to go back to Chicago that weekend. Kristin didn’t think anything of it since she had mentioned wanting to go back to Chicago recently and he had been wanting to plan a trip for them for sometime (and Reilly had been on pain medicine so she didn’t know if this was him planning something to look forward to as a distraction or for something bigger)! On the first day of the trip, Reilly had planned out a full day of activities- brunch, Chicago 360, a walk in the Lincoln Park Zoo, dinner, then a comedy show. On the walk in the Lincoln Park Zoo, Reilly got on one knee and proposed to Kristin!