Avery and Cassidy met at the College of Wooster in their drawing class. Avery was always goofing around and Cassidy was probably taking things a little too seriously, yet fate brought them together during a "speed dating" drawing exercise. They were paired together and had to draw each other's faces for twenty minutes without looking down at their pen and paper. Not long after, they attended their sports teams' formals as each other's dates. For their first official date, Avery asked Cassidy to dinner at The Wooster Inn, a charming and intimate restaurant just outside campus. It wasn't until Cassidy took Avery on her family's summer camping trip that they became an official couple. They've been inseparable ever since.

On a trip to Japan, Avery and Cassidy took a bullet train to the town of Kyoto. On the train ride there, Avery very casually suggested they fit a stop to Kitano Tenmangu Temple shrine, a place known for their beautiful plum blossoms, into their itinerary. When they arrived at the shrine, they strolled around the grounds looking for the prettiest plum tree in bloom. When they picked a tree, there happened to be a photographer there taking pictures of the flowers. Little did Cassidy know that the photographer was secretly there to capture Avery's proposal to her. After he got down on one knee, and she said 'Yes!,' they went on a photo shoot all around the city with their photographer. Afterward, they hiked up a mountain to see the Japanese macaque monkeys, where they truly felt on top of the world. To end the night, they found a tiny ramen shop that had the best ever vegan and gluten-free ramen. The chef gifted and drank sake with them to celebrate their engagement, and they left with full bellies and happy hearts.