Holli and Jon both grew up in the Scranton Area. They also both attended high school at Scranton Prep, but their paths did not cross until many years later.

One Friday afternoon in July of 2019, at the last minute, Holli accepted an invitation to travel to Baltimore to celebrate a friend's birthday. While in Baltimore, Holli was staying at a house with her friends. Little did she know that the house was owned by Jon. That Saturday morning, as Jon was rushing out the door to go to the beach, Holli and Jon met. From that moment on, their journey began.

Holli and Jon began dating very soon after they met. Jon continued to live in Baltimore and Holli lived in Philadelphia. They took turns traveling back and forth to see each other every weekend. In March of 2021, Jon decided to move to the City of Brotherly Love. Holli and Jon moved into their first apartment together in Center City, Philadelphia.

On October 1, 2021, Holli thought she was going to Charleston, South Carolina to celebrate Jon's mother's birthday. After arriving in Charleston, they went with Jon's mom, Sue, his sister, Caroline, and her husband, Chris, to visit the set of where the movie, "The Notebook," was filmed. Upon arriving, Jon and Holli took a walk down a long path lined with oak trees. As Jon's family began to step away, Jon took Holli by the hand and got down on one knee. After Jon popped the question, she turned around to see her mom, Debbie, and dad, Billy, who were flown in as a surprise by Jon for the big moment.