Ever since Jimmy’s wife died of COVID-19 during “NCIS” Season 18, the character has been through a lot, though his love for Jessica has grown slowly over the past two seasons. Casual dates laced throughout Season 19 lead to a steady connection that ultimately results in a sense of conviviality and romance. That love culminates in Jimmy shouting to Jessica that he loves her during the Season 20 finale, “Kompromat.” 

Jimmy’s declaration is accidental, but it nonetheless greases the couple’s romantic wheels; by the end of the episode, Jessica admits she loves him too, kissing him in front of their colleagues. It’s a moment that left “NCIS” fans in need of a hug, and it’s also the kind of change that helped Jimmy’s character grow.

Since then, the twosome has been publicly dating, with their relationship gradually getting more serious. These small steps have led to “The Plan,” and Jimmy meeting his possible in-law. Fans will have to wait until March 25, when “The Plan” airs, to find out how things pan out for the couple.