Sean and Maddie met on December 29th, 2018, at The Burren in Somerville, MA. Sean was in the back bar celebrating a birthday with his Acton-Boxborough crew, while Maddie was up front with her friend Mallory and other Babson friends. At the bar, Mallory spotted Joe Euele—their Babson classmate and, coincidentally, Sean’s childhood best friend and roommate. Joe introduced the groups, and Sean quickly caught Maddie’s eye as “the tallest one” in the room. She walked up and asked for a drink; Sean obliged with a vodka soda—and, in true Sean fashion, an offer of smelling salts. The rest, as they say, is history.

Their first drinks date was at Ward 8, where Maddie showed up fashionably late. Over cocktails, they spent the night trading stories about their dads, who—by pure coincidence—had both gone to St. John’s in Shrewsbury. For their first official dinner date, Sean took Maddie to Vinoteca di Monica in the North End, where good wine, great food, and even better company made for an unforgettable evening.

As they approach their wedding day, Maddie and Sean will have been together for 7.5 years. Throughout their relationship, they've explored every corner of the North End, indulging in delicious food and creating countless memories. Fun fact: Sean lived in the North End for three years before Maddie joined him, and they've spent the past four years building their life together there.

Cape Cod and Martha's Vineyard hold a special place in Maddie and Sean's hearts. Maddie spent every summer on Cape Cod. Meanwhile, Sean spent every summer on The Vineyard, where Sean's parents were married at the Harborview over 30 years ago. Together, Maddie and Sean have made unforgettable memories on The Vineyard, like taking the jeep to watch the sunset at South Beach and jumping off the jaws bridge. The magic of The Vineyard is something they deeply cherish and want to share with their loved ones.

Sean proposed on a private beach by Mayflower in Dennis, MA at sunset on September 12th, 2024. It was the week of Maddie’s cherished Dupre/Placella vacation—a tradition that has been part of her life for over 30 years and holds some of her most treasured memories. A hidden photographer captured the moment, and as Sean and Maddie walked back up from the dunes, their entire family was waiting on the deck to celebrate.

As they look forward to their wedding day at Winnetu on October 10, 2026, Maddie and Sean are filled with excitement and gratitude for the journey they've shared and the future they're building together. They can’t wait to celebrate this special day surrounded by their loved ones, creating even more beautiful memories.