The late Sarah Jacobson (she died of cancer in 2004 at age 32 and was, in the interest of full disclosure, a friend of mine), an underground filmmaker who championed a DIY ethic -- writing, directing, producing and self-distributing her work -- was best known for her 1997 Sundance Film Festival debut, Mary Jane's Not a Virgin Anymore. It was a profane teen sex comedy about a high school girl determined to understand the mechanics of female sexual pleasure by way of trial and error. It was funny and daring, as rough and cheaply made as a film could be and, most importantly, didn't back down from its subject. But that was then. Maggie Carey's The To Do List, arriving more than 15 allegedly progressive years later, does nothing but back down.
Brandy (Aubrey Plaza) is a 1993 high school valedictorian with a Trapper Keeper full of Type-A lists. She's going to college soon and wants to be prepared. But when her friends (Alia Shawkat, Sarah Steele) take her to a graduation night blowout, Brandy drunkenly makes out with the hot guy at the party (Scott Porter) and her summer plans change. Not wanting to be left behind socially in college she makes another list, one of sexual activities that would make an NC-17 movie blush. She she sets about to accomplish the hot-and-bothered tasks over the course of a summer spent working as a lifeguard at the local pool, even if it means using the sweet boy who loves her (Johnny Simmons) as little more than a prop toward her sense of adult accomplishment -- which, if you think about it, is a very cold April Ludgate thing to do.
But the list is where the "action" mostly begins and ends (if, in fact, you think the mere writing down of extreme sex acts in loopy, teenage girl handwriting is funny). There's a bit of pre-Internet amusement to be had concerning the idea of sex research, as Brandy considers asking her local librarian for help with defining some of the things she's about to do. And her awkwardness over talking about it all, even to her close friends ("Once I learn how to pearl necklace him...") is funny only because Plaza is a gifted comic actor and knows how to make awkwardness funny.
After that the comedy fizzles and extinguishes itself. The rest is all dirty talk. And for a movie that comes out swinging with a loud blast of 2 Live Crew's still-shocking hit, "Me So Horny," that's a sharp fall down a steep cliff of fake naughtiness. What's left is schmoopy moralism, tiresome third-act hurt feelings, timidity, bras-on sex scenes, slut-shaming and, most exasperatingly, overt explanations about the lightbulb moment when a teenager learns the difference between sex and love. That it's been done before and better and fiercer and dirtier becomes almost beside the point. You just want someone onscreen, anyone, to do anything dirty and funny at the same time. But it never happens. Audiences old enough to watch this film already knows everything it's selling, making it that weirdest of products with no reason to exist: the R-rated sex comedy designed for children who shouldn't see it in the first place. And all of this without a single character doing anything a tenth as interesting as having sex with a pie.
Remember, that film is called Mary Jane's Not a Virgin Anymore. Go hunt it down.