Blake and Bradley had known of each other for almost their entire lives before romantically connecting during the summer of 2019. Blake's parents, Cary and David, and Bradley's parents, Robin and William, have been friends for more than two decades, after meeting through St. Chrysostom’s Church and Day School. Blake's brother, Charlie, and Bradley also sat next to each other in their high school varsity crew boat. Although Blake and Bradley had these existing family connections, they were not close growing up because they attended different schools and had a three-year age gap. They were just Christmas card acquaintances. The Moore and Bomier parents take an annual trip to a vineyard outside Santa Barbara. During the trip, the Moores invited the Bomiers to see the new musical, Six, playing at the Shakespeare theater at Navy Pier, and to dinner at their home afterwards. They all agreed to invite Blake and Bradley since each had moved back to Chicago from different cities within the past year. Surprisingly, this was not intended as a romantic setup. Blake was too mature to date someone younger! The first thing that came to Blake's mind when she saw Bradley was, "Wow! He looks a lot different than the Christmas cards photos." Bradley told Blake later that he was excited to talk to her because of how beautiful she was. Over dinner, it was clear that Blake and Bradley had chemistry. The pair spent the later part of the evening at Chicago's classic late night spots, Zebra Lounge and The Hangge-Uppe. Thanks to Bradley's close friend Michael, Bradley was convinced to ask Blake out on a date. He took her to dinner later that July, and they have been together ever since!