Matt and Rylee first met over having many mutual friends. They both then realized that Matt was friends and hunting partners with Rylee's cousin, again through a mutual friend of theirs. The two also realized that Matt knew Rylee's brothers, Brenner and Garrett, from the Bishop Kelly ski team. They quickly became great friends and would often hang out together. It took Matt 4 tries for Rylee to finally agree to go on a date, and the rest is history!

A few days after the 5-year anniversary of their first date, on their way to dinner, Matt suggested taking some spur-of-the-moment photos in the downtown rose garden. Flowers were waiting at the gazebo with some of Ry's closest friends, expertly disguised to take photos. As they approached the gazebo, Matt panicked and got down on one knee way too quickly for the photographers. Through Rylee's shocked tears of joy, she nodded "yes" and they were engaged!