Jack and Emily met their senior year Spring Break in Cancun, Mexico. Both were students at the University of Alabama and had mutual friends, but had never met. Jack and Emily sparked a conversation about a random connection they had in common (thanks Fes!). Once they got back to school, Jack expressed interest in Emily and worked up the courage to ask her out a few times, but she turned him down on multiple occasions. Eventually Emily agreed to go to a fraternity date party where the two continued to get to know each other. After graduation, they both moved to Chicago where Jack took Emily out on their first real date to see the Chicago Cubs and the rest is history.