A playfully self-reflective rumination on what writer-director Terence Nance has described as "self-awareness through experience with love," An Oversimplification of Her Beauty is a serious but never somber offering from a member of the Brooklyn boheme 2.0 generation. After a series of title cards explains that the film will be in several parts, Nance introduces the first, a short film he completed in 2010. Sometimes exhausting and sometimes exhilarating, How Would You Feel? dissects the relationship that Nance (playing an unflattering version of himself) always wanted, sometimes thought he might have had, but could never stop playing cool long enough to go after as a very young man. The object of his obsession is Namik Winter (playing a fictionalized version of herself), a gorgeous, intelligent, self-aware young woman who's his close friend and colleague, but who never quite becomes his lover.
This first section of the film plays like a cross between a Charlie Kaufman feature and a spoof of one of those gloomy cautionary movies they used to show in health class. It details Nance's romantic frustrations and the failings that contribute to them in a near-constant stream-of-consciousness voiceover, delivered in voice-of-God tones that switch between Nance's own voice and that of The Wire's Reg E. Cathey. But even that logorrheic voiceover can't contain everything Nance has to say, so writing often blooms on screen as Nance uses a grab bag of formats, including hand-drawn animation, claymation, and grainy or badly lit amateur video, to run through a brief history of his early loves. These all blend together into one great failed romance in which the women sparkle and shine, a beautiful mosaic of self-realized sisterhood (Nance always gravitates, he says, toward a certain type of woman—"brown, maternal, well read, well traveled"—of which Namik is the epitome), while Nance himself comes off as an emotionally stunted, graceless manchild. Referring to himself in the wry third person he uses throughout this segment, Nance confesses to being a victim of "the Cosby effect"; an idyllic childhood "conspicuously devoid of angst, conflict, and repression," he says, left him unprepared to handle any of those things even in "the trace amounts that are present now."
The short is smart, funny, and beautiful to look at, but the endless torrent of self-examination and self-recrimination eventually gets a little numbing. So it's a relief when it ends and Nance the director intervenes again, introducing a short clip of himself answering a question after a screening of the film, followed by a Q&A he conducts with Namik, in which she protests that the short is just his side of the story. The tone switches here, as Nance chronicles his attempt to reestablish contact with Namik after a long absence and provides more flashbacks into their more distant past. Rather than showing himself staring at the ceiling or writhing under the covers in self-denigrating little tableaux, Nance is seen more now in documentary footage or scenes he and Namik improvised from his script about their relationship. This less filtered version of him is so charming it's easy to imagine that Namik might have fallen for him. And sure enough, the way she leans into him and some of the feelings she describes turn this part of the film into a story more of missed signals and lost opportunities than of unrequited love.
These two beautiful young people are so well suited and so clearly into one another that they make a great classic movie couple (a kid we only hear, inside a subway car where the couple with the matching oversized Afros is seen snuggling, says they look as if they're "trying to make big-haired babies"). We keep hoping they'll get together as Nance's multilayered, fractured narrative keeps anatomizing their failure to do so. That narrative, which is constantly shifting in time or darting to look at a key encounter from another angle or introduce a new thought, feels like an externalization of the workings of Vance's brain as he puzzles over the one that got away and the part he played in driving her off. We're with him all the way, rooting for him to figure himself out in time to win her over.