Anna and Conor met at Coffee Underground in Greenville, South Carolina. Anna was selling tickets for her improv team and Conor was working his first shift as house manager for Alchemy Comedy. They hit it off and went on their first date later that week at Otto Izakaya and Spill the Beans.

Conor proposed to Anna at Till's Bookshop in Edinburgh, Scotland. During 2020, Anna's study abroad trip to the British Isles had been cancelled and she was really been sad about missing the Edinburgh Fringe Festival. After meeting Anna and falling in love with her, Conor really wanted to take Anna on a trip to the festival. In addition to getting engaged, we hiked to the top of Arthur's Seat, saw 19 shows, and ate a lot of fantastic food.