Bailey and Ryan met at a lake house in Norris, Tennessee. Upon first seeing each other, Ryan inquired about Bailey and learned that she was a nurse from Cincinnati. The two hit it off immediately and spent the next 48 hours getting to know each other. They even realized that they had previously matched, and briefly talked, on a dating app earlier that year. The weekend culminated with Ryan calling his dad to inform him that he had met 'the one'. They dated long distance for the next two years with each traveling to the other's city as often as possible, meeting friends and family along the way. Bailey moved to Chicago in 2019 and the two have made a life together in the Windy City ever since. They've travelled the world, been locked in a 600 square foot apartment for weeks and everything in between; but now comes the next big step!

The proposal was perfect day that took a village to pull off. Bailey was told that they were going to Alinea for Ryan's graduation with pre-dinner drinks at their first date spot beforehand, but little did she know that they would take a walk after drinks (their normal, nightly route around the pond) where Ryan would propose. After a "yes", they then returned to their apartment where friends and family were waiting to have a surprise celebration!