James spotted Natalie at the Ss. Peter & Paul Church bazaar in September 2013 and Natalie knew who he was because she knew his sisters. They chatted and exchanged numbers and then the following weekend they went on a date to dinner at Glory Days. After a follow up hangout for James's birthday that year, Natalie said to him "I think we will stay friends." Two years later, James hit up Natalie and asked if she would be up for going out again, and she said yes, as friends.

James considered that chapter to be closed until 8 years later when Natalie's brother Greg got married and James sent her a congratulatory text. Natalie responded, "Yes, my sister and brother are both married. Now it's my turn! I feel left out!" Meant to be a joke, James sent Natalie a follow up text saying "Would you like me to do something about that? ;)" and Natalie, much to James's surprise, said "Sure we can go out!" After a more proper first date at Trummer's coffee shop, James and Natalie both felt a newfound attraction and love for each other. The rest is history culminating with a return visit to Trummer's to celebrate their one year anniversary where James asked Natalie to marry him, and she said yes!