One evening, Kailey went out to dinner at a restaurant in North Liberty, IA with some of her friends. Coleson was working that night as a server and they got seated in his section. After thinking he was super cute, Kailey and her friends asked Coleson if he was single among other questions about his life (to see if he was potential dating material, of course). After successfully answering the questions, he realized who the "single lady" was amongst the group and completely froze when he made eye contact with Kailey. Coleson walked back to the kitchen and had to get "hyped up" by the cook to go back out and talk to Kailey or else he knew he would've spoiled his chance. The evening concluded with Coleson asking Kailey to leave her phone number on a napkin. He ended up texting her and Kailey offered for him to meet her and her friends later that night after his shift for some drinks in Cedar Rapids. That's how it all began!