Chrissy and Bobby met while she was working at John Brewers Tavern. While Bobby was taking the “let them come to you” approach, after a few months Chrissy had waited long enough and asked one of his friends what his story was. On their first date Bobby was looking for a hole in the wall near his new house in Framingham. Chrissy knew just the place to take him.. the Dudley Chateau. After 6 hours just talking and completely skipping dinner they both were blown away with how much fun they had together. Through all the day trips, family time and adventuring they knew that this was the forever they both were looking for. On an afternoon in April, they planned for a leisure picnic day at Nashoba Winery. While Bobby was barely patient enough to purchase wine to share and set up a picnic, he insisted on finding a spot to “take a picture.” Chrissy was taken completely by surprise when he got down and asked her to marry him. Little did she know that he had also arranged for both of their families to be there to celebrate together shortly after.