Mary and Connor first met online through Match.com where they chatted and got to know each other for a few months. They finally met in person for the first time on Valentine's Day weekend in 2022. They were meant to go to one of Mary's favorite Italian restaurants, but Mary had forgotten about her previous commitment to her father's birthday dinner. Instead of sharing carbonara, Mary and Connor shared a few laughs over card games at her parents' house. A few months later, Mary met Connor's daughter, Lily, for the first time at the Boston Aquarium. Crafts, board games, and dance parties helped Mary and Lily form a silly and joyful bond.

Mary and Connor decided to take Lily on a special family trip over her February vacation in 2023. It was about a year after Mary and Connor met in person for the first time. During the trip, the three saw cows, tried fondue, and spent every possible minute at the indoor pool. Due to previous discussions, Mary had a suspicion that Connor had packed the ring for the trip and blatantly hinted that the chapel in the woods behind the Trapp Family Lodge would be a good location. After Mary struggled immensely with snowshoeing the length of a soccer field, the chapel plan had to be scrapped. Connor improvised by hiding the ring in Mary's things, so she would be surprised by stumbling across it.