Jess and Cole became fiends after they met each other through their mutual friend group back in 2017. By the beginning of 2018 Cole was head over heels for Jess. At one point Cole asked Jess, "hey you ever think you'd ever give us a shot at a relationship?" in which she replied, "probably not dude I just think we're too good of friends." They stayed close friends and through Cole's sheer persistence and constant flirting by the end of that year Jess knew she was in love too, and they started dating.

In October 2019, Cole asked Jess if she wanted to hang out and carve pumpkins with their friends Madison and Yarbrough. Throughout the pumpkin carving process Cole had put himself in the corner with a butcher knife and a massive pumpkin. Yarbrough was looking over his shoulder and from the other side of the room you could hear him say "make sure you keep it straight man." and "dude that looks so good." Eventually Madison and Jess went up the road to get some drinks. By the time they got back Cole was standing on the porch with Yarbrough behind him holding up a sheet. When Jess asked what they were doing Cole got down on one knee, when the sheet was dropped there was candle lit pumpkin with will you marry me carved in it. Cole asked and Jess said Yes!!