Jim knew far before Liz that this was going to be it. They met through work, where Jim played the long game and patiently waited for Liz to agree to a 1:1 meeting, which he casually suggested take place at a local dive bar. Liz arrived with her notebook in hand, certain that this was a work meeting, until Jim let her know that she could put the notebook away. They got engaged a year and a half later, visiting that same local dive bar right before Jim popped the question.