After Cassidy decided to move across the country and leave her life in Oregon behind, she ventured on a weeklong road trip with two great friends. While on the endless car rides from state to state, she decided to download a dating app called Hinge. She then received a match and shortly after, a message from Kyle saying, "big wine girl huh?". After talking for close to 3 weeks over text, Cassidy and Kyle went on an epic date which included City Winery, Tin Roof and late-night Daddy's Dogs at 2am. Little did they know, that would be their last, first date.