How To Tell You're A Douchebag (2016)

Ray Livingston is a relationship-blogging hack (“freelance writer, actually”) responsible for Brooklyn’s infamous blog, “Occasionally Dating Black Women.” The well-written, if not controversial, blog has generated some notoriety, but Ray is chafing from an overextended stay in New York, romantic ennui, and a stagnating writing career. After a particularly crappy week, he goes off on a tirade and harasses a gorgeous random passerby, only to discover that it’s Rochelle Marseille, one of New York’s up-and-coming authors. Moving to make amends in an effort to preserve his media clout, Ray is stunned when Rochelle gives him more than he ever thought she would.

Unfortunately the movie How To Tell You're A Douchebag is not yet available on HBO Max.