For years, Skylar was a regular at a bar called Bogeys. In 2014, Kylee started serving at this bar, and eventually became bar manager. He would always come into the bar, but would sit at a table, so Kylee and Skylar barely spoke to one another. Two years go by and Skylar walked into the bar one night wearing a cowboy hat. Kylee noticed him right away and secretly called him her "bar boyfriend" when he would walk in every week. Two more years go by and Kylee and Skylar are both single and have a conversation about going to Stage Coach. She gave him her number, but unfortunately he was too drunk to remember he got the digits. After a couple weeks, he came back to the bar and she called him out on not texting her, to which he replied, "I don't have your number". He felt like a real jacka$$ and made it up to her by asking her out and moving her entire apartment into her new house. The rest is history!!