Tyler and Grace first connected on the dating app Hinge, exchanging messages for a few days before planning their first date. After a brief delay—thanks to a bad 4th of July sunburn on Tyler's part—they finally met on July 7, 2022. They had dinner and drinks at Heist Brewery in Charlotte’s NoDa district. Their date lasted three hours, and by the end of the night, both were eager for a second. Around their fifth date, Grace confided in her roommate, saying, "If this man isn’t my husband, I give up." Fortunately, she was right. The next month was filled with laughter, deep conversations, and frequent exchanges of "I really, really like you." Tyler finally built up the courage to say, "I love you," for the first time while they were kayaking and paddle boarding on the Catawba River. Their relationship continued to flourish as they met each other's families, explored new places, and began attending church together, growing in both their faith and love for one another. Despite coming from different backgrounds—Tyler, a Jersey boy, and Grace, a Southern girl—they both really good feeling this was it, this was the person they were meant to spend the rest of their lives with.

Tyler and Grace had planned to visit their families in Cary for Christmas, so when Tyler arranged a special date night just for the two of them, complete with dinner reservations, Grace couldn’t help but feel somewhat suspicious—okay, very suspicious. After attending Mass, they headed to a cozy Italian restaurant for dinner. Afterwards, they strolled to the newly opened Downtown Cary Park, where they exchanged Christmas gifts under the park’s beautifully lit tree. Grace was pretty sure at this point what was going on. Tyler had one more surprise in store. He handed Grace a rather large gift bag, and when she pulled out something much heavier than expected, she was momentarily confused—and a little disappointed—to find it was a book. But within seconds, the realization hit: it was a Bible, with “Grace Pewitt” inscribed on the cover. In awe, Grace looked up at Tyler with tears in her eyes and asked, "Are you asking me what I think you’re asking me?" Tyler smiled, got down on one knee, and asked her to marry him. It was the perfect moment—the beginning of the rest of their lives together.