On the cold Sunday of January 24, 2021, James was going for a walk with his new dog, Chloe, on the Greenville, NC greenway. Taryn was nearby at the dog park with her golden retriever, Skye. James typically went to the Kinston dog park, and Taryn did not usually go to this park on Sundays. James decided to go into the dog park as well, and of course, spark up a conversation with Taryn. They talked about dogs/dog-momming/dadding for 10 minutes and then sat on a bench to discuss more about each other. James stated he could take pictures of Skye with his professional camera (which he had with him), and once he did, he said he could text them to Taryn if she put his phone number into his phone. After about an hour, the two and their dogs parted ways, ending with James stating that he would love to get a drink with Taryn sometime. Later that afternoon, Taryn texted James, thanking him for the pictures. The two agreed to meet up at Nauti Dog Brewing that evening. They talked for hours, ate street tacos by James' truck, and the rest is history.

James and Taryn had scheduled a mountain getaway weekend in Boone, NC during the weekend of November 5-8, 2021. James had organized the trip, planning many scenic stops, hiking adventures, and a secret proposal. Early on Saturday, November 6, James and Taryn (and Skye and Chloe) hiked down ice-coated rocks to reach Cascade Falls. Here, James set up his tripod for a "photoshoot" and proposed to Taryn. After initial shock and excitement, she wanted to call her parents but James assured her to wait until they got back to the car. When they got back to the parking area, James' parents and siblings along with Taryn's parents and siblings were waiting to congratulate them. He arranged for Taryn's parents to travel from Florida and for her brother and his wife to travel from Arizona. The two families enjoyed some wineries and lunch at the Daniel Boone Inn.