Jenna and Alex first met in their sophomore years of high school, but they did not become romantically involved until the following year–then split up in Jenna's freshman year at VCU (2016). They did not speak for seven years. In May of 2022, Alex reconnected with Jenna via Instagram. They rekindled their relationship from a distance the next year (Jenna living in Richmond, Alex living in Chesapeake) and visited each other on the weekends and virtually every day in between. In February 2023, Jenna took the leap and moved back to their hometown of Chesapeake to be closer to Alex. In September 2023, Alex finally proposed to Jenna at the Churchill Overlook in Richmond.