Matt planned for weeks the perfect way to propose. After selecting the perfect ring while shopping with his mom, Matt was ready to put the plan into action. He arranged for Natasha's mom and sister to occupy the future bride with mani-pedis and brunch. Matt built a large box at Blue Cork Winery with the help of Natasha's brother, dad, and Matt's mom. Natasha showed up to the winery expecting some wine with her family. Instead, there was a large blue box. Matt popped out of the box with a bouquet of white roses while "I'm Gonna Be (500 miles)" played. After showering her in white rose petals, he got on one knee and asked Natasha to marry him.