Landon and Maddy met on a random Saturday night at one of Landon's favorite places - Millside. Neither of them thought much of it at the time, as Maddy was still attending college at the University of Illinois at Chicago. But the relationship blossomed and Maddy moved home in December of 2015 after graduating. Landon never officially asked her to be his girlfriend, so each year they picked a random date in May to celebrate. Three and a half years after meeting, he asked her to be his wife! They will make it official on May 9th, 2020 - five years to the date after meeting.

Landon proposed to Maddy on a snowy Sunday in January. They had planned to grab brunch at Hidden Lake Winery with some friends. Maddy's mom happened to be at the winery at the same time (what a coincidence!) to get brunch with her friend. Standing at the counter, everyone was interested in the wines. Maddy knew she wanted bottomless mimosas (it was a Sunday morning, what else?) and didn't need to look at the wine list. Then the lady behind the counter suggested they try a special kind of wine. She placed the bottle on the table and the tag said, "Madeline Rose, will you marry me?" Maddy turned around and Landon was on one knee. More family and friends then popped out of nowhere to celebrate. It truly was the best day ever!