On May 30, 2023 Mike sent a classic message to Maddy on hinge, "Go green!" After chatting for a few days about their parallel lives of each being 1 of 3 kids of the same gender, with the same age gaps, and all having names that start with an 'M', to moving in with their siblings in Chicago and then buying a home across the street in the same years, Mike decided to ask Maddy out on a date! Their first date was to a sushi dinner and the Laugh Factory for a comedy show where they spent the evening laughing and quickly found out how much they enjoyed each others company. The similarities between them continued when they discovered their passion for golf and love for their friends and families, and that's all she wrote.

Mike had the ring in his possession for all of 24 hours before he made the proposal! He asked Maddy to go on a winter walk, which is something they do regularly. She had an inkling to the surprise that was about to incur as he had been very suspicious by scheduling this walk days in advance and making sure she knew that he got to plan where they walked. He took her to Jonquil Park, where he got down on one knee and said "something sweet" and asked her to marry him. She of course said yes, only to find that her sisters and brother in law were hiding behind a statue trying to get photos of the proposal, and had champagne and glasses for them to pop some bubbly on the spot! They were able to facetime their parents and close friends to share the good news! Later that night they got to celebrate with all of their friends at Missy and Phil's annual holiday party!