Carlee and Randy met officially on February 14, 2016 at a wrestling tournament. They began dating on March 27, 2016 when Carlee was a senior in high school, and Randy was a junior. Carlee went off to college at Plattsburgh State that fall, and returned home nearly every weekend her first semester of college for Randy's wrestling tournaments. In order to save on gas, and her parents sanity, Carlee moved back home in January and began attending SUNY New Paltz, her original first choice college. After graduating in June 2017, Randy also began attending SUNY New Paltz that coming fall where they spent the next 4 years.

Carlee and Randy always knew New York was not their forever home. Upon graduating with her master's degree, Carlee began exploring teaching positions in Virginia, where her brother Jonathan and sister-in-law Dana had recently moved. In August 2021, Carlee took a leap of faith and moved to Richmond, Virginia to begin her teaching career. Randy stayed home to finish up work, and planned on moving down in the new year.

While Carlee was home on winter break, her and Randy went to visit a friend for a few days in upstate New York who had recently built a home. While exploring the property, Randy insisted on going to see a water fall that was said to be on the property. At the waterfall, Randy got down on one knee! Carlee was completely shocked, but of course, said YES!