Gregory and Jess met in 2023 thanks to a little matchmaking magic—by Gregory’s mom, Heather, and a mutual friend who Jess and Heather worked with. Their first meeting was at work, and while Jess was feeling nervous, Gregory’s easygoing nature and sense of humor quickly put her at ease. They planned a first date and right away bonded over their shared love of the outdoors and fishing. As their relationship grew, Gregory and Jess took several trips to Florida, falling in love not just with the sunshine and beaches, but with the memories they made together. About a year and a half later, they made the exciting decision to move to Florida and start the next chapter of their lives. In December 2024, just before Christmas, Gregory proposed while the two were visiting family in West Virginia. He was so nervous, he got down on both knees instead of just one—something that made Jess burst into laughter, thinking he was joking. Once she realized it was the real thing, she said yes with a heart full of joy and laughter. They hope to continue years of laughter, joy, fishing, and travel after tying the knot.