In the spring of 2013 Anna's friend dragged her to a Georgia Tech photography club event that she wasn't particularly interested in attending. Luckily for Dylan, she went anyway. Dylan was running the club at the time and had organized an event at the historical Piedmont Park in Atlanta, GA. They spent the day cameras in hand wandering through the park. Weeks later and after multiple attempts to keep Anna involved in the photography club, Dylan finally got up the courage and asked Anna on a date. In no time, they were spending every idle moment together.

Anna had no idea what lay in store for her when she flew to Boston in December 2018. However, Dylan had been thinking of the occasion for months. The first morning there Dylan flew out of bed early and lured a groggy and mildly grumpy Anna out of the hotel with the promise of coffee and pastries at a nearby cafe. With coffee in hand and engagement ring in pocket, Dylan led Anna to the Boston Common and botanical gardens, where they strolled until they arrived at the pond. There, Dylan told Anna he loved her and wanted to spend his life with her. As they held each other, Anna interrupted Dylan's romantic speech to comment on his heart pounding out of his chest, still completely unaware of what was happening. It wasn't until Dylan had the ring out and asked her to be with him until the end of their days that she realized and said yes!