Jon and Ashley met on a dating app called Happn, for hopeless romantics who cross paths in person but never actually exchange words or contact information. They "happened" upon one another at 42nd and 5th Avenue and had their first date not far from there. They bonded initially over a love of golden retrievers and good music, attended three live concerts together in the first two weeks of knowing each other, booked a trip to a 3-day music festival one month after meeting and have basically been curating their wedding playlist ever since.

On Ashley's 30th birthday, Jon got down on one knee at the spot where they shared their first kiss: on the Brooklyn waterfront just outside the North Williamsburg ferry terminal. Jon led Ashley to dinner via ferry under the premise that they were meeting friends for her birthday and that it was the most convenient way to reach their destination. What ensued was a full weekend of celebrations, family, friends and too much champagne.