While they first met at Candler School of Theology, Brenna and Tyler didn't know each other well during grad school. Their programs only overlapped by one year before Tyler graduated. Most of his friends, though, had another year before finishing their program. Brenna became close with many of Tyler's friends who were still at Candler, but the two still didn't connect. In 2014, they both attended the same small birthday gathering for a friend, but they both brought a date! Almost a year later, in July of 2015, Tyler came across Brenna's profile on the dating app OKCupid. Figuring that she was no longer in a relationship, Tyler reached out. Brenna, knowing he was a friend of her friends, felt safe chatting with him and meeting up with him in person. They met for a glass of wine at Java Monkey in downtown Decatur. (RIP - it has since burned down!) Her friends noticed that she hadn't been that excited about a date in a while as she talked incessantly about the new guy she was seeing. A second date turned into a third, during which they met a mystical cat named Lord Whimsy and shared their first kiss.

Tyler had planned to propose to Brenna in March of 2020 on a trip to Charleston, but that trip never happened due to COVID-19. He tried to wait out the pandemic but became too impatient as the months dragged on. He wanted to come up with a plan that was both special for the two of them but also safe. On Saturday, September 19, 2020, Tyler told Brenna that he wanted to take her on a picnic. They went to Trader Joe's, picked out fancy cheeses, fruit, and champagne. Tyler drove them to Freedom Park, a park near where Brenna once lived. The two of them had previously shared an evening together looking at the stars and watching for a comet at the park - something they had done together since the beginning of their relationship. After their picnic, Tyler began his speech that would end in a proposal. Brenna, oblivious, began talking about something else. Tyler launched back into his planned monologue, and Brenna, finally realizing what was happening, slowly put down the piece of chocolate she was eating. With the words, "You are the person I want to accompany me on this journey," Tyler pulled a ring out of his pocket. Brenna, of course, said yes, and they sat in the park watching the sunset.