John and Jenn had been living in the same town of Barrington and going to the same school since kindergarten, but their paths never crossed. Looking back now; John remembers seeing Jenn in the halls and thinking she was "really cute" and a particular yellow shirt she wore, Jenn remembers John as the "super popular guy". John and Jenn both decided to go to Valparaiso University, John being a grade older. During her freshmen year in 2013, Jenn and John started having mutual friends and having their eyes on each other. They danced together at Darkside 2.0 and were beer pong partners at Sig Tau another time. Some more time passed, and John messaged Jenn on Facebook to check in on her freshman year. After a few exchanged messages, they made plans to spend time together that following weekend. It's fair to say fate continuously brought the two together.

On June 8th, John took Jenn for a walk along the lake where they ended up at Belmont Harbor. To her surprise, a captain came out and said he would walk them to their private sailboat for the evening. He sailed John and Jenn around Lake Michigan for a few hours. They say it was an indescribable and euphoric feeling. Jenn thought it was extremely romantic and the best thing anyone had ever done for her, especially considering her love of sailboats. About halfway through the ride, John gave Jenn a beautiful letter. He then got down on one knee and said “Jennifer Lynn Reed, will you marry me?”