In Spring of 2019, Caitlin's roommate, Shelby Williams, worked as a hostess at the same restaurant where Dylan bartended and served, and she helped introduce the two of them to each other. Their first date was at Mad Taco in College Station, TX, on March 14th, 2019.

On December 23rd, 2024, Dylan proposed to Caitlin on the field at Bobcat Stadium (now UFCU Stadium) in San Marcos, TX. Caitlin was at Dylan’s apartment in Austin before the two would be spending the holidays with his family. The plan was simple: Dylan would pick her up after work and drive straight to dinner with his dad and stepmom in Fort Worth. Just before arriving, Dylan called Caitlin saying he’d “forgotten his wallet” at the football facility, so they needed to swing back by before they left town. Annoyed but cooperative, Caitlin agreed to tag along for the (now extended) journey. When they arrived, Dylan led her toward the football field to “look for his wallet.” As soon as they walked onto the field, “At Last” began playing over the stadium speakers. At the 50-yard line, Dylan got down on one knee and asked Caitlin to marry him, while Caitlin’s sister and brother-in-law, Christina and Bryce, secretly captured the entire moment. Turns out, there was no forgotten wallet and no dinner plans in Fort Worth!