In August of 2019, Andrea was working alongside Jeff's friend, Anna. That summer, Andrea organized a fundraiser at a bar in Boston for the Falmouth Road Race. At that event, Anna shared a video of Andrea on her Snapchat story, and Jeff couldn't help but be instantly smitten! Anna, along with her roommates Caroline and Flavia, invited Andrea and Jeff to meet at their rooftop on Commonwealth Avenue later that month. The rest, as they say, is history!