By their sophomore year, both Caleb and Kylie had become single following challenging breakups. During this time, they grew closer through their shared interest and hobbies, such as hiking and anime. After a reflective camping trip with friends, Caleb realized that the qualities he valued in a partner—someone who was a good friend, virtuous, independent, fun, energetic, driven, and intelligent—perfectly described Kylie. This realization led to them dating, and after a few dates, Kylie invited Caleb to her brother’s send-off party. At this family gathering, Kylie’s mom introduced Caleb as Kylie's boyfriend. This marked the official start of their relationship on March 18, 2017.