Alison and Tommy met at a commercial real estate holiday party held at the Palms in Boston. The party was hosted by Tommy's former employer J.Calnan & Associates. Alison and Tommy were introduced by a mutual friend.

Tommy proposed to Alison at their home in Charlestown during a Patriots game on November 12, 2017. He was planning a proposal for later in the week with family and friends but had the ring in his possession and couldn't wait any longer! Just as Alison got tired of watching the game (after about two plays) and started to leave the room Tommy got down on one knee!