It's a tale as old as time: Olivia and Jordan matched on Hinge, exchanged a few messages about prior trips to Israel, followed each other on Instagram, and then didn't speak for five months. Jordan posted an Instagram story of the Chicago skyline in December, to which Olivia reacted with "🥶". Jordan seized the moment, finally mustering up the courage to send a follow-up message on Hinge that said "Hey, sorry, I fell asleep" and Olivia took the bait. Following that incredibly smooth start, Jordan really knocked it out of the park by picking a phenomenal first date spot: Farm Bar, where the only gluten-free item on the menu was Brussels sprouts. They were delicious, as were the Old Fashioneds, and Olivia agreed to a second date... and a third... and within weeks had invited Jordan to join her family vacation in Clearwater, FL. After some action-packed trips around the country/globe and a few Dave Matthews Band concerts, Jordan knew he had found the one and got down on his knee in front of that same skyline that started it all.