After a long year of long distance, Maddox had a plan to propose. On October 10, without Gracie knowing, Maddox traveled from Vermont to Tennessee. The journey came with its challenges, including a 12-hour flight delay followed by another delay. Maddox had to stay the night in Boston, but he eventually made it. Gracie had no idea maddox was coming, and thought her and her roommates were going to do a photoshoot together. Gracie was completely surprised to see Maddox waiting for her as she arrived at Morris Vineyard.