Jerry and Emily met in a way some might say is unconventional, but by today's standards is pretty much the norm. They met on Hinge, a dating app they both were on while living in Philadelphia. Jerry first messaged Emily about her love for tacos and asked her to go to Rosy's Taco Bar for their first date. During the date, they hit it off so well that Emily asked Jerry to meet up with her and her friends at Frankford Hall the next day. From there the rest is pretty much history - they went on to spend every weekend together and their love for each other developed quickly as they realized they were a perfect match. Their dates consisted of going to different restaurants, enjoying the success of Philly sports, meshing friend groups, and walks around the city that led to trying many different coffee shops. Jerry and Emily's love not only developed in Philly, but over many memorable trips including New York, Charleston, Dominican Republic, various US National Parks, and Greece where they got engaged.

At first, Jerry thought he was going to propose during late summer of 2025, but once they started planning their trip to Greece, he knew it was an opportunity he didn't want to miss. Prior to the trip, Jerry contacted the hotel and coordinated with a local photographer to help capture the moment. From there, he spent a few weeks messaging the photographer and came up with a great plan to surprise Emily during the first full day in Santorini. The day came and Jerry was ready, but the only problem was Emily wasn’t complying with his plan. Emily wanted to head out to dinner around 5:00 to make sure they didn’t miss the sunset, but Jerry had to stall until 7:00 to meet the photographer. Emily wasn’t too happy about this wait, but she was about to experience the best moment of her life. To distract Emily and ease her mind for the time being, Jerry recommended a local restaurant before dinner to get a quick drink. After the drink, Emily wanted to change into running sneakers for the walk to dinner, but Jerry told her it wouldn't be a good idea - and that's when it finally clicked. Jerry led Emily to the hotel lobby to “ask the front desk a question” as an excuse to run into the photographer (Gesti) who was waiting for them. As Jerry talked to the hotel manager, Gesti introduced himself to Emily as a local photographer. Following the script Jerry wrote for him, Gesti told Emily there was a young couple staying at the hotel that had just cancelled their session with him and offered his photography services for free. From there, they took a few pictures at the villa and a few spots around town. Jerry's goal was a private proposal on a balcony with the sunset in the background, and it couldn't have turned out more perfect. After the engagement, they were able to relax and enjoy the rest of their trip before arriving home as Fiancés.