AG & Douglas grew up in the same town and attended the same high school, but definitely did not have the same circle. Douglas was 4 years ahead of Anna Grey, so they had very little interaction until about 2 years after AG graduated high school. Douglas was coaching her brother in football at the time, and the two ran into each other one evening in Columbia. They always made plans to go out or catch up but something always came up.

In the fall of 2018, Douglas called AG out of the blue, and made plans for a Sunday evening together. An already nervous Anna Grey texted Douglas that she was on the way to meet him. Douglas, who had fallen asleep, woke up and frantically texted that he would be "a little late." An hour later, he showed up & swept AG off her feet. (She forgave him for the time thing.) The two quickly connected and have been smitten ever since.

In December, AG and Douglas traveled to New York City with his mom, Lisa, and stepdad, Robert. It was AG's first time in NYC, and it was Christmastime. Everyone was just so excited to be there. The last night they were there, Douglas (secretly) scheduled a carriage ride through Central Park. The guide informed everyone that we could stop to take pictures along the route. When they arrived to the Bethesda Fountain (an icon in many films & TV shows set in NY), naturally AG wanted to go get a closer look and take pictures. When they stopped under the bridge for a picture, Douglas knelt down on one knee and asked AG to marry him. Through happy tears, she said yes, followed by "Do I have to put the ring on myself?"