Henry’s premise was to update When Harry Met Sally for the millennial generation. Like People We Meet on Vacation, the 1989 movie features opposite-sex protagonists who appear to have nothing in common, and yet following a carpool ride home, embark on a decade-long friendship steeped in sexual tension. In the movie, numerous obstacles arise to delay the eventual happy ending. This narrative trope is appealing to consumers, who have the satisfaction of watching characters change over time, the slow chemistry build, and the rewarding romantic outcome. Arguably, the idea of friends becoming lovers after a decade of getting to know each other is also alluring because it is so rare in real life—especially amongst a millennial generation known for its need for instant gratification, restlessness, and shifting loyalties. Still, while the narrative trope is unrealistically romantic, it taps into more common experiences such as putting off the expression of romantic feelings towards a friend and pulling away from intense intimacy due to the fear of loss.

Though Henry imitates elements of When Harry Met Sally’s narrative structure and spotlights a heterosexual romance, her characters express a more modern understanding of gender.