Cailyn and Bobby's love story began in July 2016, at the extremely romantic, Landsdowne Pub. Cailyn was convinced last minute to go out, and met Bobby at the end of the night. Their first date was at Davio's, where Cailyn met Louie for the first time as a puppy. They traveled the world, including a cross country road trip, and celebrated many milestones together. Bobby planned to propose to Cailyn in December 2021 with help from his dog, Louie. After dinner at Maggianos in Boston, Bobby proposed at Boston Common in front of the Christmas tree, where Louie had a sign around his neck saying “will you marry us”. We are so excited to begin the next chapter of our story with all of you!