Bailee was in Dubuque to watch her brother, Adam, play basketball back in January of 2020. He played for Simpson and Bailee and her family would often come to town early to check out the local breweries and wineries. This time, her cousin Ryan brought along his friend to Potosi Brewery (Surprise, it was Jake!) Afterwards, Bailee texted Ryan letting him know that she thought his friend was cute and asked for his number. Jake and Bailee began to message each other for about a month before it fizzled out because of the pandemic and also Jake lived in Milwaukee and Bailee in Iowa City at the time. Fast forward a year and a half later, they reconnected over social media and picked up where they left off. After many months of attempted planning, they finally went on their first date after some convincing on Bailee's part ;) The rest is history!