Doug and Annie met for the first time in summer of 2017 at an event where Doug was skateboarding with Annie's brother, Ian. They crossed paths several times over the next few months. Ian told Annie that Doug was a great guy, meanwhile telling Doug that he would be great "Brother-in-Law" material. When Doug's birthday came around that October, Annie plucked up the courage to ask him out for drinks. They spent their first few dates sharing countless pitchers of Yuengling at the Cage in Squirrel Hill, seeing the band Waxahatchee live in Lawrenceville, visiting Phipps Conservatory, and back to the Cage for a few more rounds. A year and a half later, Annie and Doug moved in together into an apartment in Regent Square, introducing their cats Pigeon & Willow. Later that year, they adopted their dog Bean, making their lives a bit more chaotic. In December of 2020, they closed on a house together in Braddock Hills. On Annie's birthday, May 31st 2021, Doug proposed to Annie in front of a group of their friends and family. Annie couldn't say "yes" fast enough.