Picture it: Loyola University Maryland, 2016 (yes, a shameless Golden Girls reference to start this off). At the time, Ian was in his senior year at Loyola, and Jess was in her sophomore year. Jess ended up befriending Ian's roommate's girlfriend at the time. See the connection? Great. The first time Jess remembers seeing Ian was in the dining hall when she was having dinner with friends. Rob and Ian came over and said hi to the table, and Jess looked at Ian and was like WHOA. WHO IS THIS HANDSOME FOX?! Needless to say, an impression was made. Fast forward to November. Jess was on an outing with some friends, and they wound up going back to her friend's room. And who was there? You guessed it, IAN! But naturally Ian was leaving right when Jess got there. Rude. But anyway, the next week, Jess and her friend went to the boys' apartment to hang out. Ian FINALLY noticed Jess and asked her to play 20 questions. Very cheesy, but it worked. Ian and Jess were out on a date two days later. And, as they say, the rest is history.