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Jess and Simon met on a friend's couch in 2019. Things didn’t get serious until 2021 when they started watching the show Odd Taxi together at Jess’ apartment every week (it’s a cartoon about a Walrus that drives a taxi, it’s really good). After Odd Taxi ended, Simon asked Jess to go see Annette at the Gene Siskel Film Center (it’s an opera about a puppet, Adam Driver is the puppet’s dad, it’s actually not that good) and this was their first official date. Despite taking her to a mediocre film, Jess thought he was worth another shot and they’ve been together ever since. Now they take turns picking movies. Although, they did have a potentially severing argument about the merits of the movie Challengers in 2024. In the fall of that year, for the first time ever, Simon dressed better than Jess for a date night. She grew suspicious something was up, and as usual she was correct. Simon proposed with his great-grandmother’s ring, and Jess said yes immediately after bursting into tears. Don’t worry, he was crying too.