December 31, 2014 Before there was Brad and Jess, there were three friends: Brad, Brad's friend Joe, and Brad's friend Joe's girlfriend Jenn, also known as Jess' sister. On December 31, 2014, Jess drove up to Dedham, Massachusetts, to visit Jenn for her birthday, and Brad received a text from Joe, inviting him to an impromptu birthday/NYE celebration. The rest is history.

December 27, 2019 Five years later, Brad and Jess were ringing in the New Year in Houston, Texas. But before that, they decided to spend a few days in the City of Austin. On their first day, they woke up early (strangely enough, this was Brad's idea), and walked to the diner for a quick breakfast (one of them still dreams of the biscuit they had that morning). After they filled up on biscuits, they proceeded to drive 40 minutes outside of the city to the popular tourist spot, Hamilton Pool. It was the one destination Brad wanted to see and put himself in charge of planning. When they made it to the entrance, they were told they'd have to wait an hour to park, something neither of them were expecting on an off-peak weekday. Being the planner for this particular destination, Brad had the final say in whether they were going to stick it out in line. Luckily, the line moved fast, and they were able to park not too long after. They walked the trail leading down to Hamilton Pool, and Jess immediately planted herself in one spot and began snapping pictures. Maybe knowing he'd be there for a while, Brad took this opportunity to make his move. He got down on one knee and did just about the only thing that would break her gaze from the crystal blue pool. Which brings us to what's about to come next...