Jack and Madison like to pretend that they met during their years as lifeguards at Sandy beach, in a similar way to Jack’s grandparents. Although the real story starts a few weeks after Madison moved back to Cohasset, MA from Nashua, NH. As the new girl in a small town, Jack saw her in the local convenience store, Tedeschi’s, and walked over and formally introduced himself by shaking her hand in the bread aisle. For Madison and Jack, there was an instant spark. Within months, they were on Sandy Beach where Jack asked Madison to be his girlfriend on the 4th of July in 2012. Jack and Madison were high school sweethearts and continued their relationship through out college. They visited back and forth between College of Charleston in South Carolina and High Point University in North Carolina. After 4 years of a long distance relationship through their college years, Madison and Jack moved into their first apartment together in Boston, MA in the fall of 2018.

On August 28th, 2021, Madison and Jack returned to Sandy Beach for yet what would become another memorable milestone. Madison had been expecting to have brunch with the Leffel family to celebrate Jack and Watson’s upcoming birthdays. As they neared the Cohasset Country Club for brunch, Jack received a call from Watson. Their dad, John, had accidentally left his phone at the beach while walking their dog. Madison and Jack took a quick detour and arrived at Sandy Beach. They started heading down the boardwalk where the “fake phone” was supposedly left behind. When Jack said where on the beach the phone was, coincidentally in the same spot they started dating, that was when the alarm bells started to go off! Madison was thinking how ironic it was she and Jack where on Sandy Beach dressed up and realized what may be happening. Jack asked the most important question, and from the there the rest was a blur of emotions as Madison said, ‘Yes!’. After they returned to the Leffel’s house, Madison was surprised again to celebrate their engagement with her family who had flown in from different parts of the country. It was an incredible day!