Brad and Jess met in August 2017 in Fort Collins, CO while working on the special education team at Kruse Elementary School. They bonded over their love of travel and working with kids. Their work relationship developed into a friendship and then evolved into a crush. While out with friends one night, Jess boldly shared her feelings and luckily Brad reciprocated.

In April 2022, Brad and Jess headed down to Montrose for Jesse's “surprise birthday party.” The party was complete with streamers, party hats, and takeout. After dinner, it was announced that they would be heading to Telluride in the morning to go on a hike to continue the birthday festivities. When they arrived at Bear Creek Trail, it was packed with snow up to their knees, but they trekked ahead. The hike ended with Brad on one knee, asking if Jess would marry him. She said “yes” of course, and asked afterwards about the surprise party. It turns out, it was never about the “surprise birthday party.”