Jess and Will met at Marple Newtown High School in September 2009. They were friends for more than a year before going on their first date in January 2011 to the AMC Marple movie theater. Will officially asked Jess to be his girlfriend on February 3, 2011.

After nine years of dating—which included four proms, two Temple University degrees and two years long distance while Jess worked in Boston—it was time to pop the question. Will planned to propose to Jess on her 27th birthday on October 11, 2020 on a picnic in Valley Garden Park, but the weather had different plans and they were rained out. Undeterred, Will rescheduled for the following weekend in the same spot on a sunny, crisp autumn day. He got down on one knee and asked her to marry him. Guess what she said?