Skylar and Kayleigh met by chance. Kayleigh went to Hampden-Sydney her first weekend of freshmen year at Sweet Briar. Kayleigh was hanging out with a few people she had met prior to moving to Virginia for college. While hanging out in a dorm with a few others, Kayleigh was sitting in the corner by herself. Skylar walked into the room and immediately started talking to everyone. He noticed Kayleigh in the corner by herself and invited her to sit on the couch next to him. They hung out for the rest of the night as Skylar showed Kayleigh around Hampden-Sydney's campus. Kayleigh had to leave for a 6AM lift but Skylar made sure to get her snapchat before she left. As Kayleigh got into the car with her friend to make the hour long drive back to Sweet Briar, she claimed dibs. On the drive back to her school, a message from Skylar came through when she got service. It said "Let me know when you're back on campus. Bed's warm, beer's cold. I think you're pretty cute." The rest is history.