Jack and Maddie first met each other in middle school but became friends in high school, during Jack's junior year & Maddie's senior year. They started dating shortly after and the rest is history.

During the Galt's annual Ocean City, NJ beach vacation, Maddie thought they were going down to the beach to take family photos; Jack had other plans though! He walked Maddie down closer to the water, got down on one knee, and asked Maddie to marry him in front of both of their families.