They first met during the Summer of 2013 but didn't cross paths again until work brought them together in May 2016. While Justin was in Palo Alto for Associate training, he asked Jess to "kill time" with him at Press Club - a wine lounge in San Francisco. Jess, always up for befriending coworkers, agreed. She didn't think much of that night (other than that he must not have had very much fun because he declined a second glass of wine), but Justin left 100% convinced it was a date. Even after returning to New York, Justin was persistent, but Jess being completely oblivious actually attempted to set him up with a friend. Five long months later, at an Associate Offsite, his efforts paid off, as Jess finally started to notice Justin. He was still based in New York, but he called Jess every day until they started dating in January 2017.

One weekend in January 2020, under the guise of planning a romantic weekend for their Anniversary, Justin insisted on being in charge of the entire weekend’s itinerary, which made Jess slightly suspicious because he typically does not plan anything. Refusing to tell Jess where they were going, she had to pack four bags for two days: two for clothes, one for shoes, and one for purses. As ridiculous as it sounds, she had to prepare for everything – hiking, fine dining, swimming, etc.! The whole weekend in Napa was a happy blur. Justin proposed at a winery and had their hotel room decorated for once they got back from dinner. But the best part of the weekend: Knowing how much family means to Jess, Justin had Jess' parents come up to Napa the next day for a surprise celebration and lunch at the Auberge du Soleil!