Dillon and Cherise met back in high school at Georgia-Cumberland Academy when she was a sophomore and he was a senior. They became close friends when they went on a mission trip together to Holbrook, Arizona, to serve at a local Seventh-day Adventist Native American school. They stayed friends afterwards, but lost contact before Dillon joined the US Navy. Three years later, they reconnected while Dillon was deployed in the Middle East. Their conversations went from text messages to phone calls whenever Dillon had cellular service. It was as if a day hadn't gone by since they last spoke! Dillon asked Cherise to be his girlfriend on October 28, 2023, and they later reunited when Dillon flew back from his deployment on February 5, 2024.
Dillon knew that one of Cherise's favorite movies was Up, so he decided to buy the Adventure Book from the movie for her as a Christmas present. He also told her that he had booked a photographer to take photos of them to place in the book. However, he didn’t disclose the location and surprised Cherise with a beautiful waterfall backdrop. On January 1, 2025, Dillon got down on one knee and asked her to marry him.