Written, directed, and starring Trevor Moore and Zach Cregger, 2/5ths of the sketch comedy group The Whitest Kids U Know, Miss March chronicles both one man's lifetime infatuation with Playboy magazine and another man's apprehensive four-year attempt to lose his virginity to his girlfriend. The former, Tucker (Moore), has been obsessed with the cultural implications of the high-end porn mag since he first got a glimpse of one of the Pamela Anderson issues. The best friend is Eugene (Cregger), a high-school student who doubles as an abstinence lecturer. Along with his devout girlfriend Cindi (Raquel Alessi), Eugene recounts how his brother had sex and then had "retard babies" that later went on to burn down his house and kill his mother. The tirade is accompanied by projections of Syphilis-infected no-no areas.
With prom around the corner, Cindi insists that since they are so totally made for each other they should go all the way. At the behest of Tucker, Eugene gets hammered and before he can go upstairs and enjoy the best eight seconds of his life-to-date, he falls down the stairs and lands a coma for four years. Awakened by a medical advent called "The Bat Trick," which consists of Tucker hitting him in the face with a Louisville Slugger, Eugene comes to find that Cindi is now a Playboy Playmate. Serendipitously, the upcoming weekend offers a chance for all the Playmates to converge on the Playboy Mansion, and the two friends take to the road while also evading Tucker's epileptic girlfriend (Molly Stanton).
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