Caitlin and Ray were living lives barreling toward one another. Both moved to Chicago chasing the desire to see more, learn more, and be more. A month before Ray moved to Chicago, he was in town for a job interview, that morning he stopped into a neighborhood restaurant to grab breakfast. Little did he know, his future wife was working at the juice bar next door. After getting the job, he moved to Chicago, and after losing the job a year later, he met Caitlin. At a bar in Logan Square on a December night, their paths crossed again. Feeling bold, Ray asked if he could buy her a drink. A few more drinks and three hours of conversation followed. A few years passed full of conversations, singing, and reality TV, they decided to keep it going forever.