How To Tell You're A Douchebag
Directed by Tahir Jetter
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.
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★★★★ review by Dylan Moses Griffin on Letterboxd
The main character, Ray Livingston, has a job that seemingly only exists in film. He runs some dating blogs, and somehow makes a living from it. Scenes predominantly feature young people who seemingly have nothing but free time to walk around and talk to each other, and eat with each other at fancy restaurants. This is the type of movie and characters I frequently hate, so why did I find myself loving it so much? Why did it feel fresh, original and unique, like something I had never seen before? Because these were roles and depictions always reserved for white actors.
★★★★½ review by MovieMavenGal on Letterboxd
Ray Livingston is a blogger (Occasionally Dating Black Women) and plays the field -- dating multiple women at once. He confronts a woman on the street, and she gives him the dressing down of his life, calling him out as a douchebag.
His friend Jake tells him the woman he just accosted is none other than Rochelle Marseilles, a famous writer for Mahogany. Ray tries to apologize, but puts his foot in his mouth yet again as he blogs while drunk. But the sparks have been flying between the two. Rochelle agrees to go out with him, and they have a wonderful weekend together.
Then Rochelle has brunch with her girlfriends and meets Yasmin, who had been dating Ray. Ray doesn't understand when Rochelle doesn't want to see him again -- why didn't she feel the magic he did?
Charles Brice is fantastic as Ray -- he's a jerk, but a very charming one! Dewanda Wise is an arrogant and flawed Rochelle -- she may seem to have her act together, but the relationship misfire is not all on Ray. The highlight of the film is the supporting players, Jenna Williams as Yasmin, Alexander Mulzac as Rochelle's boyfriend Paul, and especially William Jackson Harper as Ray's friend Jake.
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