Matt and Haley first met during his Senior and her Junior year of high school in Groton, MA. In the spring of 2011, Matt asked Haley if she would be his date to his Senior Prom, and she said yes! While both shared mutual "crushes" on each other, they were also very shy and never dated. Eventually they went their separate ways, with Matt attending Bentley University and Haley attending Loyola University Maryland the following year.

Matt made the most of his time at Bentley and being in the Boston area, while Haley eventually made the decision to move to New York City after graduating from Loyola. They reconnected in 2019 when Matt visited NYC to see a few mutual friends from high school. After a couple of years checking in on one another on social media and weathering the early days of the pandemic, Matt learned that Haley had moved back to Massachusetts and asked her on a formal date. They've enjoyed every minute of life together since!

Matt and Haley decided to take a trip down to NYC to celebrate their second dating anniversary, which happened to be on a Friday. Haley booked the accommodations, made a dinner reservation, and picked out a summery dress for the occasion. Little did she know, Matt was making his own plans and hired a photographer to meet them in South Cove Park, right at the time that he was planning to propose. Haley and Matt were fond of their pre-dinner walks through the Charlestown Navy Yard, and Matt knew that she wouldn't mind going for short walk before heading over to their reservation. In a neighborhood where some of Haley's favorite memories were formed during her post-college years, Matt got down on one knee and asked her one of the most important questions of their lives. After Haley responded to Matt's proposal with the easiest and most enthusiastic "yes!", the two were elated to participate in an engagement photo shoot with the photographer who captured their special moment. They topped off the night with a romantic dinner and drinks to celebrate!