Chris Waitt turns the camera on himself after realizing every girlfriend he's ever had has eventually dumped him. In his mid-thirties and single again, he sets out to track down his exes one by one, sitting them down on camera to ask what actually went wrong. The answers are blunter than he expects, and the film catches him flinching, arguing, and occasionally laughing at his own excuses as the pattern becomes impossible to ignore. Waitt widens the search beyond his own relationships, visiting a sex surrogate and a men's confidence seminar in an attempt to diagnose himself from the outside, and the tone stays self-mocking even when the material turns genuinely uncomfortable. Shot in a low-budget, handheld style with Waitt narrating his own humiliations, the film works as both comedy and unsparing self-portrait. By the end the question isn't whether he'll fix himself, but whether he can sit still long enough to hear what the women in his life have been telling him all along.