Romantic Cringe-Comedy

A NSFW example of the genre:

Ivan Kander calls Dinner With Holly the “illegitimate love child” of Curb Your Enthusiasm and American Pie:

The style of humor, while scripted, feels delightfully improvisational. The characters in the film are flying by the seat of their pants, and the audience, in turn, is buckled in for the awkwardly satisfying ride.

The film’s natural, yet hilarious, style is no accident. The entire creative team is close in real life: Kristin Slaysman, who plays Anna, is director Josh Crockett’s girlfriend, and Bridget Moloney (the titular Holly) is Dan Sinclair’s Wife. Bob Turton, who portrays Rob, is an old friend from Northwestern. The film was shot over the course of two days in Dan and Bridget’s house, with the rest of the crew consisting of close friends and other former classmates (including DP Dustin Pearlman). That camaraderie definitely comes through in the film—only people this comfortable with one another could make their audience feel so uncomfortable.