Kaity and her friends from high school have an annual tradition of celebrating the Fourth of July with their friend Andrea at the DiMayo's house in Easton, Maryland. In 2021, Andrea's cousin Christian invited his best friend Taylor to come along for the weekend, which is when Kaity and Taylor met for the first time. Kaity had just moved back to Baltimore from Chicago and Taylor was living in Wilmington, Delaware. Soon after meeting one of them was always traveling up or down I-95 to spend the weekends together before moving in together at the end of 2022.

Taylor completely surprised Kaity when he proposed on the beach in Lavallette, New Jersey! After taking a walk down to the beach, Taylor sneakily set up a tripod and his phone to capture the moment.