Jack and Amanda attended Hinsdale Central together, both graduating from the Class of 2007. Amanda was a star on the cheerleading squad and Jack was a bit of a nerd, thus their paths did not cross very often. A fateful night in November 2017 brought the two together when each attended The Hinsdale Central Class of 2007 Ten Year Reunion held at Hubbard Inn in downtown Chicago. The two made a connection, chatted over tequila shots at the bar, and later headed to karaoke at Mothers with other high school friends, some which they had not seen in a decade. A few days later, Jack got the courage to ask Amanda on a date at Happy Camper, where they unironically shared a meal of jalapeno poppers and jalapeno-topped pizza, all while sipping on Pink Flamingos (the restaurant's signature cocktail, also featuring jalapenos). The date was really heating up! They moved on to an impromptu game of beer pong at Mothers Too, and topped the night off with live music at the iconic Zebra Lounge piano bar. After two weeks of dating, the two took the BNSF train out to the western suburbs to each spend time with their families and hopefully have a chance to spill the tea about their new potential love interest. They said goodbye to each other as they departed at different train stops… only to collide two hours later at a favorite Italian restaurant of both families, ZaZa’s in Clarendon Hills! You know as they say.. the rest is history!

In July of 2022, Jack and Amanda joined her family for a special vacation week on Hilton Head Island to celebrate her parents Barry and Debbie's 40th anniversary year. Before heading to the airport, Amanda joked to Jack, "If you have any precious cargo, make sure it's safe!" hinting to any intention of proposal, unaware he had done just that. On day three of their trip, all were awoken by the knock of a professional photographer scheduled for a 6:30am sunrise photo shoot for the whole family (it was initially scheduled to be a sunset shoot the day prior, but there was a change of plans and everyone rolled with the punches, sacrificing two hours of sleep for what proved to be a very memorable morning). After family photos were taken, Jack got down on his knee and surprised the family with his proposal to Amanda. All celebrated with champagne on the beach afterwards. It was an exciting Tuesday morning indeed!