Duke and Madi grew up five minutes around the corner from each other but didn't meet until she was 15 and Duke was 17. Duke happened to go to Madi's high school homecoming in February of 2013 and afterward, they both attended the same after-homecoming party where Duke approached Madi. A few days later Duke invited Madi to hang out at a friend's house. Madi saw Duke later that week and they spent the entire night talking and laughing... the rest is history.

Duke asked Madi if she'd like to go down to Chicago for dinner and drinks. Madi got ready for the evening out in the city, but Duke had bigger plans in mind. Duke drove Madi to their favorite rooftop in Chicago for pre-dinner drinks. Except, instead of taking them to their table, the host led them to a secluded cupola where rose petals and champagne waited. From there Madi immediately knew what was about to happen. They celebrated together that night in Chicago and returned home to a house full of family and friends who had surprised Madi to celebrate.