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A Complete History of My Sexual Failures is a documentary film directed by and starring Chris Waitt. In the film, Chris explains to viewers that every single girlfriend he has ever had has broken up with him. He explains the different ways women have dumped him, including by email, by voicemail, and one woman even writing a book, killing off his character. But what Chris does not understand is what he is doing wrong so he decides to go on a mission, finding each of his ex-girlfriends and asking them what he did wrong. At first, none of the women are even willing to talk to him. When they do, he finds out the various reasons why his relationships have failed, including his messy appearance, his dirty apartment, and the fact that he is unemployed. Chris's outlook on life changes when he gets surprising news from his ex-fiance, the only woman Chris really cared about.