Cynthia was Alan's swim coach when he was training for a triathlon. Although Alan did not continue lessons for long, they remained friendly and in September 2017, they went on their first date.
Under the guise of just another vacation, Alan suggested a trip to Key West, Fl. to get away from cold weather. Alan also suggested that they should invite friends and family on the trip. With the intention to propose on the beach of one of the most remote state parks in the country, Alan's plans were thwarted by bad weather. Plan B (but more like Plan H) Alan proposed at the Southern Most Point in front of Cynthia's parents and friends, much to her surprise.