Simon completes Zoey's love triangle and is Zoey's first crush in the show, although he is engaged to someone else. Zoey and Simon help each other at work, but they grow closer as Simon tells Zoey about his own family tragedy. Eventually, Zoey is afraid that Simon's fiancée Jessica might think that she and Simon have feelings for each other. At the end of the season, Simon kisses Zoey and breaks it off with Jessica – maybe for Zoey, or maybe not.