After running in the same circles for a couple of years, they were both invited to a mutual friend's house early June of 2020 - they hit it off and went on their first date about a week later to Island Hideaway. The couple spent a lot of time together throughout the rest of the summer before Jake asked Hailey to officially be his girlfriend on August 15 - he'd actually asked the week prior but considering Hailey's answer was "sure", he chose to ask again and she never lived that down! In May 2025, they went on a trip with some of their best friends to Myrtle Beach - unbeknownst to Hailey, Jake had been planning since February that he would be proposing on this trip and had let all their friends that would be there in on the secret. On May 15, Jake surprised Hailey during a beach photo session with the group and asked her to marry him - this time she did not say "sure" and instead said "yes" immediately...after she asked him if he was joking! The couple celebrated 5 years together in August 2025 and have experienced so much in this time - best friends' weddings, annual Ocean City trips, travelling abroad to Ireland, Jamaica, and the Dominican, moving in together, taking on new hobbies, and overall the ups and downs that come with life. Now it's time to move onto the next adventure - getting married!