While a sophomore in college, Nate hosted a party for all of his Weddington high school friends at his parent's home (unbeknownst to them) during summer break. Nate and Ashley met through a mutual friend that night and Nate professes that it was "love at first sight". Over the course of the next four years their great friendship grew into more, culminating in an engagement in December of 2022.

Nate planned to propose to Ashley while in Europe, during a Christmas vacation with the Dracon family. Extensive arrangements had been made for a romantic evening proposal in Prague prior to meeting the rest of the family in Vienna later that week. Travel delays and lost luggage drastically altered that plan. The engagement ring was secretly stowed away in Nate's luggage throughout the duration of the trip (and constantly checked on!). Presented to Ashley in the gardens of Notre Dame Cathedral on the final evening of their stay, the couple celebrated their engagement by toasting with a bottle of Billecart champagne and a French baguette, shared while overlooking the lights of Paris at night.