Kaileen and Grant met through the MIZZOU college radio station KCOU 88.1 FM. In the spring of 2014, Grant was an anchor on the drive-time news hour "The Pulse" and Kaileen was the producer. They ran in the same friend circles and one day, Kaileen had the thought that Grant might be a good friend to ask to her sorority formal. After the formal, Grant asked Kaileen on a sushi date. The day of their first official date, in an out-of-character move, Grant's professor decided to end the class by playing the song "Friday I'm In Love." Grant took it as a good sign — and it clearly was because they've been together since that day. On Groundhog's Day, February 2, 2019, Grant asked Kaileen if she wanted to walk by the water outside of Gantry State Park. He got down on one knee and asked her to marry him. Then, they went to celebrate with friends at a party Grant and Dani Sirtori-Cortina (Maid of Honor) planned at one of their favorite local spots, Alewife. In their spare time, Kaileen and Grant enjoy cooking together, playing Scrabble on their rooftop, taking walks in Gantry State Park, and grabbing a beer with friends.