Dalton and Caitlin met briefly while attending college at SDSU in April of 2020. After realizing they both grew up in Rapid City, they exchanged Snapchats and parted ways. They met again during the Rally in August when Caitlin accidentally messaged the wrong 'Dalton' to come visit her at work. Dalton spent the rest of the night partying with Caitlin's roommates.

Later that month, Caitlin and her roommate, Jolene, were socializing at the infamous Rays Corner, where Dalton bartended. After a few consecutive nights there, Jolene talked Caitlin into making a move. Caitlin sent Dalton a snapchat, which he blatantly ignored (he has his own excuses as to why). Eventually, he figured it out. Caitlin and Dalton began dating on September 12th of 2020, and then engaged on October 11th, 2023.