At 16 years old, Ashley went off to college- much to her parents displeasure. There she moved into Conrad Hall, which would turn out to be a blessing in disguise. James, a sophomore at the time, was living in Conrad for his second year at Stetson. They had seen each other around before, but a few months into the school year they got to know each other. A few weeks and some awkward dates later, they started dating on Ashley's 17th birthday.

Almost two years later, James finally got down on one knee on September 24th. It was the middle of the day on a Tuesday, but he "just couldn't wait anymore." After a sweet coffee date, he asked Ashley to marry him in the comfort of home and she couldn't stop crying. They then went for a little walk and it was the best day ever.