Melissa and Grayson met in 2018 through one of Melissa’s friends in Indianapolis. They had interacted briefly on numerous occasions, but it wasn’t until St. Patrick’s Day in Chicago that they truly connected. After a long day of celebrating a friend’s birthday on a trolley bus, Grayson asked Melissa for her number. At the time, Melissa showed little interest but gave him her number anyway, not knowing it would be the start of something really special. The two stayed connected, chatting every day over text—so much so that Grayson decided to switch from an Android phone to an iPhone so he could FaceTime her. Grayson won Melissa over when he drove all the way to Chicago to help her after she inevitably broke her foot (again), only to drive her back to Indianapolis so she could catch a flight for a vacation with her girlfriends. They continued chatting throughout her entire trip, and upon her return, they decided to make things official. With Grayson living in Indianapolis and Melissa in Chicago, their relationship involved a lot of back-and-forth travel, which eventually led to Grayson moving to Chicago in 2020. They navigated moving in together during COVID, welcomed their beloved goldendoodle, Poppy, in 2021, and three years later, Grayson popped the question at Olive Park near their first apartment together.