Ben and Kailey met on a dating app called Bumble in August of 2020. After texting and realizing they really hit it off, they met for their first of many pizza nights at Proto's Pizza in Broomfield, Colorado on August 25, 2020.

Every year on the day after Thanksgiving, Ben and his brother Lukas and sister-in-law Andi go to the forest to chop down their Christmas tree for that year. Ever since November of 2020, Kailey joined them for that tradition. On the third consecutive year of doing this together, Ben proposed to Kailey next to their Christmas tree surrounded by Lukas, Andi, Kailey's parents Elizabeth and Scott, and all of their dogs (Gamgee, Dakoda, Montana and Quincy) After they chopped down their trees, they headed for downtown Denver for dinner at Venice Italia, where they happened to see the Union Station annual tree lighting ceremony. (Ben claims he totally planned that out)