Kaitlyn lived with Kristy McLarnan, a cousin of Bradley's, while attending UCF. One evening, Kristy went out for dinner with her family. Kaitlyn was sitting in the living room watching The Office when she heard the front door open. She expected it to be Kristy returning from dinner, but instead it was Bradley who walked through the door. He introduced himself to Kaitlyn and sparks flew immediately. A year later, they finally saw each other again and went on their first date.

After winning Fantasy Football, Kaitlyn and Bradley decided to use the winnings on a Disney vacation. They both enjoy EPCOT and have had many fond memories there. So that was where they went. As they walked around the World Showcase, Bradley kept pausing in all the locations that were special to them, like Mexico and Japan. He found obstacles at each stop, so they kept walking. Kaitlyn asked to go into the Rose and Crown in England since they had never really explored that area. It was very crowded but they found a cozy corner to hang out and talk. As they started to have a heartfelt conversation about their relationship and their future, Bradley got down on one knee and asked Kaitlyn to marry him. She said, "Yes!"