After the two matched on Hinge, Cassandra would drop hints and imply that she and Zachary should go on a date three different times over one month. Cassandra finally leaped and asked Zachary out one night after work. They meant to watch the movie Halloween at Axelrad in Houston on October 30, 2019, but they ended up talking all night. Just after midnight, it was starting to rain when Cassandra asked, "May I kiss you?" Zachary responded with a swift yes, and the rest is history.
Zachary surprised Cassandra with a proposal in an art gallery in New York City on January 24, 2025.