While attending a 24 hour running race the two saw each other out on the trail many times throughout the course of the race. They connected as friends on Instagram but didn't start chatting until the following spring, connecting over an obstacle race. After that it's no shock that their first date was in June 2021 at a Tough Mudder.

The two made the trip up to Vermont to compete at the Spartan Killington Ultra in September 2023. Jessica's race didn't go so great with a sprained ankle taking her out for her first DNF while Charles crushed his previous time by two hours. The following day the two took the Gondola up the mountain for what Jessica thought was just a trip up to enjoy the views, while Charles had other plans. Needless to say Jessica's weekend quickly turned around.