Diamond and Trey met on a dating app. Diamond reached out, commenting on how cool it was that Trey was learning to fly planes. He followed up asking her about the musical instruments that she plays. One week after they started messaging, they had their first date at Irina's Crepes. The conversation flowed so easily that they kept talking until the restaurant closed.

Two weeks before proposing, Trey received his private pilot license which meant that he could finally fly with friends and family. His first choice was Diamond. On the day he proposed, he flew her from Martin State Airport to Cambridge Airport where they had breakfast at the airport diner. Trey flew them back to Martin State and drove home. At home, Trey got down on one knee and asked Diamond if she would marry him. She said YES!