After Tom started a new job as a Podcast Producer in Nashua, the happy couple decided to celebrate with a weekend away in Boston. The proposal was in September, but the planning started much before that. Tom bought Shannon's engagement ring back in July of 2021. Fast forward to September, Tom was so excited to start a new job that he could not hold back his plans any longer. Shannon and Tom stayed in the Seaport District of Boston for their weekend getaway. During the day of the proposal, they enjoyed the city they had spent so much time together in throughout college. Later in the afternoon, they got ready for dinner in the North End. Tom suggested taking a water taxi to dinner, but since it was taking too long, they ended up calling an Uber. Shannon and Tom had a delicious meal at Nico Ristorante. Tom barely talked the whole time - he was so nervous! After dinner, Tom suggested they take a water taxi back to the Seaport since it wasn't possible earlier. He said he would show Shannon where the water taxis pick up in the North End, which happened to be right next to the bench in front of the building Tom's parents used to live in. On April 28, 2017, Tom had sat with Shannon on this same bench and promised he would propose to her at this same spot exactly four years later. Despite being a few months late, Tom kept this promise.