It was Parent-Teacher night in the fall of 2021 at Atlantic Christian Academy- Jessica ("Ms. Fender") was working as an Upper School English Teacher. Isaiah came straight from work to support his sister, Isabelle. Isaiah and Jessica were instantly drawn to each other, but they would not meet again until he started attending Anchor Church, where Jessica was a worship leader. Isaiah served on the production team, which kept the two in close proximity to get to know each other. They remained "just friends" until August 16, 2023 when they realized the feelings they had were more than friendship material. Isaiah and Jessica were frequent fliers of their local Chili's, watched all genres of movies and documentaries, and were no strangers to an after church nap on the Fender's couch. They also enjoyed roadtrips to Disney where they discovered each other's music taste, talked about their childhoods, and talked about their future. They dated until August 30, 2025 when Isaiah (FINALLY) popped the question!