When Maddy was a sophomore at Indiana University of Pennsylvania and Kevin was a freshman, Kevin was randomly paired with Matt and Noah, two sophomores Maddy had gotten to know the previous year. Kevin and Maddy were first introduced to each other in August 2018. By the end of that fall semester, Maddy and Kevin had gone on their first date—bowling at Mohawk Lanes in Indiana, Pennsylvania—and were officially dating.
Kevin and Maddy arrived in Hawaii to celebrate both Maddy's parents' 30th wedding anniversary and her father's 60th birthday. While waiting for her family to arrive, they went for a walk along the water. Kevin led Maddy to a stunning spot with rocks near the shore, where he could get closer to the water. As Maddy turned around, she was surprised to find him down on one knee!