Early August 2017, Kaitlin was starting her last semester at GSU, and Jamie was getting ready to return to college in Macon. They had recently both found themselves in a position where they were open to dating, and conveniently their close friends, Grantson and Sarah Martin, knew this. In a matter of days, numbers were exchanged, plans to have dinner were set, and the frat boy was driving from McDonough all the way to Statesboro to take the pageant girl on a date. There was no doubt in their minds this would be a one-time deal and both were sure there wouldn't be a second date. Grantson was also very sure Jamie and Kaitlin would either love each other because they were so similar or they would kill each other for the same reason. Luckily for them, great conversation was made and at the end of dinner neither was ready to say goodnight. Jamie almost got thrown out when while getting ice cream after dinner he ordered orange sherbet in a waffle cone, but Kaitlin kindly looked past this strike. Before the evening was over, second date plans were laid, and now forever plans are in the works!
Despite their many amazing qualities, Jamie and Kaitlin have always lacked in their ability to take pictures together. After moving in to their home in Macon, they decided it was time to have professional pictures taken. Knowing this, Jamie started laying the ground work for this proposal months in advance. Jamie reached out to his friend and handled all of the scheduling for the big day. On April 24th, 2021, the rain would not stop. Kaitlin was nervous that her hair would fall, which it did, and Jamie was nervous for other reasons. Despite the rain only letting up slightly, it was too late to turn back. Jamie put on his jacket, where the ring was conveniently hid, and the group headed outside. As the camera snapped pictures, Jamie gave the signal and prepared himself for the big question. As he had done so many times before, he told Kaitlin that he couldn't wait to marry her and she echoed the sentiment. Asking her then if she "wanted to get this party started" to which Kaitlin responded with a confused face. Jamie promptly got down on one knee to ask the fateful question. Kaitlin responded with sobs and head nods but whimpered out a yes! After additional pictures, a quick celebration, and calling family, Jamie and Kaitlin went downtown to celebrate. To Kaitlin's surprise, Jamie had planned an engagement party with many of their closest friends there to surprise and celebrate the newly engaged couple!