"Romantic Comedy" is Curtis Sittenfield's ode to the classic genre that also confronts its problematic beauty standards and gender roles at the same time. While at work for The Night Owls, a late-night live comedy show, sketch writer Sally Milz notices her coworker Danny has started dating a celebrity actress who recently guest-hosted the show. It's a phenomenon she's familiar with: average men dating women significantly hotter than them — so she turns it into a scathing bit for the show. When pop star Noah Brewster appears on the show to guest host, he and Sally hit it off, but Sally questions if the desirability dynamics she notably made fun of ever work the other way around.