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Rooftop showed Chris Waitt‘s humorous narrative short “Dupe” a couple years ago, so I was very eager to check out his debut feature. The slick short starred Chris as an extremely lazy hipster who orders off the internet a cloning machine (that looks like an crappy old photocopier) so he can send his dupes off to work for him. (We actually showed that film in a program, about labor and industry; indicative of Rooftop’s attempt to mix serious and silly films in themed programs.)

A Complete History of My Sexual Failures” is a hysterical and inventive personal documentary which reveals that Chris is every bit the extremely lazy hipster he appeared to be in “Dupe.” After realizing that he’d been dumped by every woman he’d ever dated, Chris decides to try to make a film of self-discovery: why do ladies drop him as easily as he drops his dirty clothes on the floor?

The first handful of exes he contacts dismiss him out of hand, with Chris demonstrating his deadpan ability to get rejected and to say the wrong thing. When interviewing a young lady on the street, he asks her how long her boyfriend’s penis is. Her reply: a shy smiling “Uhh, me mum’s right there.” It’s only when Chris’ mum gets out some old love/hate letters sent to her son (one of which is addressed “Dear Shit-Fuck), and negotiates interviews on his behalf, that he is able to even really communicate with any other woman.

And that’s when we get to see that his awkwardness and social irresponsibility isn’t just limited to pestering women on the street; his failures run far deeper. From the interviews, a pattern emerges: he’s uncaring, constantly late, a liar, and in one instance even tried to kiss his girlfriend’s mother. One woman is so ashamed of having dated him, she only agrees to be interviewed behind a curtain, typing her humiliatingly harsh answers into a computerized voice machine. In the Q & A following the screening, Chris pointed out that he’d really allowed these women to “discover their inner anger.”

One former fling who is a self-described sex addict reminds Chris that he was unable to perform in bed, he is forced to admit (in front of a wide-eyed female hotel clerk) that he’s impotent. The film then really goes wild, with Chris seeking medical help, getting advice from drunks on the street, and visiting a dominatrix who literally whips his balls, in full view of the camera, in an uproariously funny sequence which is sure to vindicate many of his former lovers. Finally, Chris OD’s on Viagra (and beer), and runs around the streets asking women to fuck him. Call it his own “Super Size Me” moment.  

The film is certainly part of the growing trend of “stunt” documentaries, with these numerous set pieces that wouldn’t be happening if not for the camera. One has to wonder at points if Chris isn’t hamming up his own lack of awareness, his own ignorance of basic human relationships. But I think Chris and these women are being pretty earnest. The fact is, Chris is a charming, attractive, creative, hip guy: women really want to love him. But he’s also solipsistic and painfully uncaring, and so he disappoints his girlfriends badly. If he was just a dumb schmuck, none of these women would care one way or the other. But the fact that he does have so much potential makes the sting of his failures all the more poignant, and makes the film all the more compelling.

Chris does learn some lessons from the process. For one, he heals his relationship with his longest-running girlfriend, and now that she’s had a baby, Chris seems to gain more respect for her, and seems to actually acquire some sense of responsibility. Even more amazingly, Chris ends up in a long-term relationship with one of the women he accosted during his little blue pill freak-out. At the Q & A, she said that remarkably she hadn’t seen the film until now (a sign of both his insecurity and his callousness, it would seem), but though she was quite shocked by the film, she claims he’s been a much better boyfriend.  

When asked if there was anything that was too embarrassing to put in the film, Chris said that it was all damn embarrassing, “but I had gotten some funding, and there comes a point when people have put all this time and effort into the thing, and I couldn’t go back. I wondered when it would ever end, because after all, it’s my life. And believe me, it wasn’t good news for me when the film got into Sundance. I was like, ‘Oh no, now even more people are going to know what a fuck-up I am.”

That he is, but a charming and delightful one, who has made a daring, insightful and hilarious film, one which really fits with Rooftop’s ethos of showing personal documentaries, even “home movies.”