Hayley and Matt met the classic way that so many couples do - through a dating app! Matt approached Hayley with the verbose and creative opening line of "Hayley!!" (Hayley likes to give him a hard time for using such a lame opening line; however, Matt argues that Hayley was crazy enough to take the bait and respond to it.) After a quick back and forth, Matt suggested they meet for drinks at Theater on the Lake. What Matt may have lacked in terms of digital pick-up lines, he more than made up for after meeting in person, as he and Hayley quickly bonded over drinks and easy conversation. It didn't take Hayley and Matt long to realize they had more in common than they initially thought, having grown up in the same suburban area of Chicago and attended neighboring high schools. In true chivalrous fashion, Matt offered to walk Hayley home along the lakefront at the end of the evening, and the rest, as they say, is history.

In planning his proposal, Matt's main concern was surprising Hayley. Matt had secretly been working with both of their families for weeks to plan out the perfect proposal. He enlisted his brother Kai’s help to scout out a secluded spot along Chicago's lakefront trail to pop the question. He then arranged for Hayley's sister Reese to hide nearby with a camera to photograph the special moment. Hayley had made dinner reservations to celebrate the two-year anniversary of their first date, assuming those were the end of their plans for the evening. To her surprise, after dinner, Matt suggested stopping by Theater on the Lake for drinks to commemorate their first date. Once there, Matt got increasingly excited and confident about his plan, rushing them through drinks so they could walk to his pre-determined spot on the lakefront. As they got closer, Matt secretly motioned to Reese to ready her camera, got down on one knee, and proposed! They celebrated the proposal to the cheers of nearby onlookers. Matt then continued the evening with one final surprise: a night at the nearby Hoxton Hotel, complete with drinks and dancing at a speakeasy jazz club, Lazy Bird. Everything about the evening was perfect in every single way, and saying yes was the easiest answer Hayley has ever given.