In 2018, Matthew and Chiara were lucky enough to cross paths at Maryland Avenue Elementary, where Matthew was Chiara's "boss". It started as a friendship, although Matthew seemed to show some preferential treatment towards Chiara while working together. Once Matthew moved on to another school, the friendship slowly turned into more. The rest is history.

On an amazing vacation where Chiara showed Matthew parts of Kauai that she spent most of her childhood summers, Matthew popped the question during a walk on Anini beach.