Madeline & Dylan met when they both worked at the Mark Twain Brewing Company in 2020, and they quickly formed a friendship while working together. After Madeline finally gave in to Dylan's persistent attitude, they began to hang out every single day and never looked back since. They began officially dating May of 2021.

Dylan had planned to propose to Madeline in Mexico that December, but his excitement got the better of him. Instead, he suggested a surprise pre-school-year getaway, and Madeline quickly organized a weekend in Chicago, one of her favorite cities. On the morning of their trip, Dylan was unusually insistent about looking nice, while Madeline wasn’t thrilled about being up so early to catch the train. Once in Chicago, they headed to Navy Pier, where Madeline complained how she wanted to stop and eat because she was hungry. Dylan took a chance and asked a couple to take their picture. As they posed, Dylan dropped to one knee and proposed! Madeline was overjoyed, forgetting her hunger and admitting Dylan was right about dressing up. They spent the rest of the weekend celebrating their engagement and exploring the city they both love.