Dean and Julia met on Bumble. Their first dates were a competition of whose city had the better margaritas. Dean chose to make his own (using a measuring cup and store bought mix) and thus he lost. Had he brought Julia to Locos, his original plan, he would have won. Many bets, games, and competitions have ensued since. After Dean proposed on a private charter in the Boston Harbor, the couple realized they had spent all three anniversaries on a boat by chance. They are continuing that tradition with their wedding, which will have the cocktail hour on a boat and will occur on their fourth dating anniversary.