The couple both agreed to go on a blind date through mutual friends, not knowing much about the other. As individuals, Chris and Jess, tend to be considered the "shy one" in their friend groups. Which meant it took some time for each to come out of their shells. But once they did... they never looked back! The couple started dating immediately, falling for each other rather quickly. However, the thing holding the couple back was not knowing if Christopher would be returning to Florida in the fall of 2018. Yet, the couple decided long distance could work because neither could say goodbye. They had faith it would work in their favor. The following winter of 2018, each met the other's family for Christmas. The couple most recently celebrated their 4th anniversary together on December 23, 2021.
While dating, Jessica visited Christopher many times in the mountains of North Carolina where he worked during the summers. Since being a Florida native, the mountains always felt special to her, but even more so because they represented their relationship. Therefore, when it came time to choose a special place for the big question, Christopher knew it should be in the mountains. He had been planning the moment for about a month and even had the ring shipped from a family jeweler in Florida. He planned to propose during one of their usual hikes. The two went on a hike at Grandfather Mountain, off a dirt road, on the side of the cliff where he said... "This is it!", got down on one knee, and she said, "Yes!".