In the fall of 2011, Ashley & Jamar were both recovering from failed relationships and were stuck in a rut. Both the Bride & Groom shared a mutual friend in Carnegie Wise, in whom they had confided about their dating woes. Carnegie suggested that Ashley & Jamar go on a date and hoped that it would help them to get over their exes. Ashley has often remarked that while she didn't know the role Jamar would play in her life, from the first moment they were introduced, she felt a "spark". While romance did not bloom immediately, a friendship began. In 2013, Jamar saw Ashley at Carnegie's wedding and knew he had to convince her to go on a date. After about 3 months of pursuing her, Ashley had a change of heart and she and Jamar shared a meal at Yesterday's. During that time, Ashley's maternal grandmother had just passed away, and Jamar became a shoulder for her to lean on. In March of 2014, Jamar asked Ashley if she would be willing to go on another date and by July, they began dating exclusively. Even though it didn't begin like most fairy-tale romances, Ashley and Jamar take pride in knowing they wrote their own love story.

When Ashley & Jamar began dating, Ashley's grandmother Christine had just passed away, and she often told Jamar that she wishes that the two could have met. So when Jamar began to plan the proposal, he knew he wanted to find a way to make sure that her missed loved one was still a part of the big day. A week before the proposal, Ashley had originally planned to head to Charlotte to see friends from college, however Tisha and Sam convinced Ash to come home to the Lowcountry instead. On Sunday June 11th, 2017, Jamar asked Ashley if he could join her for service at her family church. As they walked into the church, Ashley noticed that all of her and Jamar's families and friends were there. Ash immediately asked what was going on, and everyone replied that they were there for Family & Friends Day. Just as the pastor was about to give the benediction, he told everyone that there was a special announcement, and asked for Jamar to come forward. Jamar took the mic, explained that he was in love with Ashley, and that he wanted to ask her to marry him in the one place where Ash felt closest to her grandmother. As he began to choke back tears, he said "I'm just going to go ahead and ask", and dropped down on one knee. Jamar was barely able to get "will you marry me?" out, before Ashley said yes!