Quickly after we began dating we realized that we both had family ties in the Abruzzo region of Italy. In October of 2019, while traveling to visit the villages our families were from (which were less than 3 hours away from each other) we stopped in the small town of Santo Stefano di Sessanio. Jackson proposed to Kelly at the base of Rocca Calascio, while she was atop a donkey following a beautiful hike through the Apennine mountains. She immediately said yes, quickly followed by "I need to get off this donkey."