Matt and Melissa met in 2021 when Matt became the School Resource Officer at Hoosick Falls Central School, where Melissa is a teacher. After years of friendship, they went on their first date in 2024 (kindled by a night as "dates" chaperoning the Junior Prom).

In July 2025, Matt joined the Zimmermanns on their annual Cape Cod vacation. On the way home from dinner on the first night, Melissa asked Matt to stop for ice cream (which is not outrageous, because they eat ice cream at home 7 nights a week). Matt said no, but Melissa was persistent. They finally stopped at an ice cream stand attached to a mini golf course, where Melissa ordered ice cream alone - and it was the worst ice cream she's ever had. When they got back to the house, the whole family prepared to play games in the backyard. Melissa's sister asked for her help with figuring out how to use the kayaks that were attached to the dock. When they turned around to walk back to the house, Matt was on one knee and caught Melissa by complete surprise. Although the shock didn't allow her to say anything at first, Melissa answered with a very confident “Yes”!