Growing up on a small island, Harry and Gaby knew each other for years before they started dating. As Harry says, he always had a crush on Gaby but she was the friend of his older cousin Brooke, and so he kept his distance. They ran into each other one day in 2016, and Gaby felt an undeniable spark but Harry was touring at the time, so their run-in was short lived. When Harry moved home to Bermuda in the spring of 2023, he and Gaby reconnected immediately. From their first date, both knew they'd found their person. And the rest, as they say, is history.