Although they had crossed paths through mutual friends before, Anna and Shea officially met 3 years ago. Anna was bartending her way through grad school at a neighborhood bar in Shadyside and Shea was selling beer in the city. It just so happened that the bar Anna worked at was one of Shea’s favorite accounts. One evening while Anna was at work, Shea came in for an outing with his co-workers. Anna’s friend Jill who she worked at the bar with was also a friend of Shea’s and, once Anna told Jill how attractive she thought Shea was, Jill introduced the two that night. After the initial introduction, Shea came to realize that Anna worked every Tuesday so he made certain that Tuesday was the day of the week he would stop in to take care of his work-related business and, of course, talk to Anna. The first time Shea and Anna hung out together was at a bar on Mount Washington. He had told Anna he wanted her to come to the movies with him and his friends but she turned him down and said she would meet him after so she could be with her friends as well in case things went downhill. Needless to say the two hit it off and it turned out to be the night that would start the rest of their lives together. After a year of dating, the two moved into their home on Mount Washington together where they currently live.

Their Mount Washington love story continued when Shea proposed to Anna in Grandview Park. Although Shea had told Anna that they were getting their annual family photos that evening, he had other plans of his own. When the two showed up to the park and no one besides the photographer was to be found, Shea got down on one knee and popped the question. After she said yes, they headed to Grandview Saloon for what Anna thought was a champagne toast for just the two of them. However when they got there, to Anna's surprise, both of their entire families were waiting to celebrate with them.