Maddy met Charlie when she was in middle school because her older brother was best friends with his older brother. This brief meeting turned into a crush that went on all through high school and into college. Charlie and Maddy both went to UW-Platteville, and Charlie is convinced that Maddy "followed" him there. In her sophomore year of college, Maddy finally worked up the courage to talk to Charlie. After a few months, Charlie finally asked Maddy to be his girlfriend!
Originally, Charlie had asked Maddy to take a weekend trip to Chicago with his sister-in-law Toni. Maddy vetoed this trip as she and Charlie had just visited Chicago and they were both still on a college budget. Charlie couldn't push this trip on Maddy without raising suspicion, so he had to quickly plan a new, more cost efficient weekend to pop the big question. Charlie and Toni quickly planned a trip to the Milwaukee Zoo because Maddy is an animal lover. They decided to end the day at the beach. On the way to the beach, they passed a beautiful fountain in a park and after hearing Maddy comment on how pretty the spot was, Charlie decided it was perfect. While at the beach, Charlie and Toni were plotting the moment behind Maddy's back. They finally left the beach and it was time. Toni asked Maddy if she wanted a picture with Charlie at the fountain and to her surprise Charlie lowered to one knee. They were both covered in sand and were wet from the beach, but the tears were flowing and the moment was perfect! Maddy was completely surprised and was shocked that Charlie pulled off such an amazing moment without her knowing!