Even though Blair and Miles both grew up in Roslyn, they did not meet until much later in life. Not until a summer weekend in Fire Island did the two cross paths, thanks to their best friends who were dating at the time. It took Miles some time (several months) to finally have the courage to ask Blair out. But after their first date on Halloween they knew there was something special. Several years later, Miles popped the question at a palace in Sintra, Portugal!