Riley had recently moved from Boston back to her hometown of Dallas, Texas to start a new teaching job. She was invited by her friend and future co-worker Harry to a Deep Ellum bar to meet up with some friends. There, she encountered Samuel telling a story to the whole group. Soon after, Samuel and Riley were formally introduced and they spent the rest of the evening talking to each other. When they both noticed the time (it was 1 o'clock in the morning), they realized the rest of the group left long ago. Samuel walked Riley to her car and asked for her number and the next day they scheduled their first date. Four weeks later, Samuel told Riley he loved her.

Samuel and Riley talked about a Maine trip on their first date together. Both wanted to specifically visit Acadia National Park. They scheduled the trip for June of 2021, first spending time in Portland and then driving up the coast of Maine to Acadia. On the fifth day of the trip, they got up early to go to the less-frequented side of Acadia called Schoodic Point. With the entire area to themselves, Samuel proposed and Riley said yes.