Caleb and Kylene met through mutual friends after attending a college party. Caleb was driving that night and picked up a group of people, including Kylene. The two hit it off immediately. They all went back to his suite and spent the night talking and getting to know each other. Before leaving to go back to her place, Kylene made sure to get Caleb's number so that she could message him when she made it home safely - AKA an excuse to get his number. In return, Caleb made sure to give her a sweatshirt to wear for the night - AKA an excuse for her to bring it back the next day.

After trying to plan a trip to Greece during the 2020 quarantine and that proposal plan falling through, Caleb had to come up with another idea to propose that was just as amazing. In July, Kylene found a photographer who was going to Asheville and looking for models to take couple pictures. After booking that photoshoot, the couple finished planning their trip. With no idea that Caleb was going to propose, Kylene kept saying little remarks about the possibility of an upcoming proposal. She kept saying, "You know what would make this outfit? A diamond ring." He followed up with, "I don't even have it." On the day of their photoshoot, Caleb had to secretly find a spot to propose. Right before he dropped to one knee, Cooper Blue, their beloved dog, almost gave the whole thing away with his barking. When it happened, everything was just perfect.