It was a perfect summer day in Chicago on the Saturday of Labor Day Weekend 2019 when fate fell into place. Matt spent the afternoon at a Cubs game tossing back Margaritas with his friend. Brooke spent the afternoon at the Houndstooth with friends, drinking Coors Light, and watching Alabama football (Roll Tide!). After the games ended, Brooke and Matt both ended up at a bar called Country Club. Matt and his friend were making one last lap around the bar when rumor has it that Brooke "made eyes" at Matt. Their groups started mingling and Brooke and Matt hit it off. Their first date was later that week and the rest is history!