Jackie and John were both members of the same wedding party in June of 2019. During the event, while John was waiting at the bar, he engaged in a conversation with Jackie about the signature cocktail. Although it seemed like a casual exchange at the time, little did they know that it would hold significance a year and a half later. In December of 2020. John chanced upon a mutual friend, the bride from the wedding, having dinner with Jackie. Interestingly, he inquired about her. They went on their first date on December 13th, 2020, just before the closure of restaurants in New York City. By the end of that evening, both felt a spark and meaningful connection, and have remained together ever since.

John proposed to Jackie hiking to a vantage point overlooking the Boca do Inferno of Sete Cidades on the island of Sao Miguel, the largest island of the Portuguese Azores archipelago. This location, with unbelievable views, holds a profound significance that will remain a cherished memory forever.