Aubrey Plaza Goes Nerdy '90s in 'The To Do List' Trailer (Video)

Think of it as Ten Things I Hate About You: Sex Ed. Edition.

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Following her role this summer as a college-age intern at a Seattle magazine in Safety Not Guaranteed, Aubrey Plaza goes back in time to play a high schooler working her way through the pains of social and sexual awkwardness in the 1990s-set comedy, The To Do List. In this first look, it's clear that both the film's fashions and intended discomfort deliver a whole world of nostalgic pain.

Written and directed by Funny or Die's Maggie Carey, the film puts Plaza in fantastic rounded glasses and skorts as she sets off to figure out the world of sex, which to her dismay mostly consists of things that end with "job." Joining her in the adventure are a whole slew of comedy co-stars, including Donald Glover (who tops Plaza in the fashion department with his overalls), Andy Samberg (with hair and hoodie to die for), and Bill Hader. Also involved are Johnny Simmons, Clark Gregg and Christopher Mintz-Plasse.

The film, it was announced Wednesday, will hit theaters on Valentine's Day 2013.

A warning: the trailer is red band and slightly NSFW.