Caleb and Lilly met in their Middle School Drama Club during the production of Bye Bye Birdie. To Caleb, Lilly was an annoyance at first always messing with his hair, bothering him, and constantly annoying him trying to get his phone number. To Lilly, Caleb was the cutest boy in school, with a lovely angelic voice. He was kind, caring, and hilarious. So she obviously had to pick on him. From that point, Caleb and Lilly became great friends and started developing deeper feelings than just a friendship. In the summer of 2019, Caleb and Lilly officially started dating. Since then, they have been high school sweethearts, and are now attending college together.

Going on walks have been Caleb and Lilly's favorite peaceful activity together. On the morning of July 22nd, 2023, Caleb and Lilly decided to go on an early morning walk together to try and beat the heat. The sun was shining through the trees on this brisk summer morning. One of Lilly and Caleb's favorite things to do is to look at the sun shining through the leaves. The wonderful sun beams and the different shades of green can be so mesmerizing. As they were walking down the paths, they stopped to look at the sun shining through the leaves. Lilly went to hug Caleb, as he was behind her. She started flailing her arms trying to reach for him. After her arms finding nothing, she turned around to see Caleb on one knee.