Jacob and Madison met on August 23rd, 2019. It was the first day of Freshman year at Saint Mary's University of Minnesota located in Winona, MN. The school had put on a freshman bonfire/game night that Madison and her roommate attended. There, they met Jacob and his teammate, Alex Keeler, who is one of Jacob's Groomsman. Immediately, Madison had a crush on Jacob.

At the bonfire, the four decided to go to Target to pick up a few items. Jacob offered to drive, and Madison really wanted to sit in the passenger seat next to him, but her roommate beat her to it, so she ended up sitting in the back of the car with Keeler. After the Target run, Madison's roommate asked if Jacob or Keeler knew how to set up the TV in their dorm room to the school's internet. Jacob said he could try, so the four went to Madison's dorm to do so. At this time, the four exchanged Snapchat usernames and followed each other on Instagram. Jacob never did get their TV set up that night.

After Jacob and Keeler had left Madison's dorm, Madison sent Jacob a Snapchat saying thank you for trying to set up the TV, but the real reason was to start a conversation with him. He replied instantly and the conversation never stopped.

Jacob came back to Madison's dorm a couple weeks later and eventually got the TV all set for the school year. This happened to be the start of their love story.