The Story of Jacquelyn and Anthony

Their story begins long before they even realized it was being written. They’ve known each other since middle school, though their paths seemed to always run parallel rather than intersect. Jacquelyn was best friends with a close family friend of the Sasso Family, and as time went on, their connections grew deeper, but still, they remained just out of reach.

In high school, they found themselves even more entwined with each other's lives. Jacquelyn became friends with Anthony’s younger brother, Joseph, while Anthony was friends with Jacquelyn’s older brother, Christopher. Their lives were so closely knit, yet we never quite connected. They’d see each other often when Jacquelyn would wait around for wrestling practice to end so she could practice pitching. But still, they were just two people in each other’s orbits.

Fast forward to the summer of 2019. Both of them were set to work at the “On The Go” town camp in Chappaqua. The day after orientation, Jacquelyn had plans to attend the Pride Parade in the city with another camp counselor, Emily Antes (bridesmaid). There was just one small problem: neither of them were 21 yet and needed someone to help them buy beverages (we will use this word for legal purposes 🙂). That’s where Anthony stepped in. Being over 21, Emily suggested asking him to help out. Not only did Anthony agree, but Emily also felt bad for not inviting him, so she asked him to join them at the parade.

The next day, on the train ride to the city, Anthony handed Jacquelyn a canned Margarita, and in that moment, something changed. Flirtation began to bubble up between them, and it wasn't long before Emily left the two of them alone to meet up with another friend. As they wandered through the vibrant streets of the city, Anthony grabbed Jacquelyn’s hand, and suddenly, everything just clicked.

What started as a simple favor turned into an unforgettable day—and the beginning of their adventure together. From that moment on, their paths weren’t just parallel anymore; they were forever intertwined. And the rest, as they say, is history.

❤️ A special shoutout to Emily Antes on being our matchmaker ❤️

Bridgewater Marriott