So what’s next on Aubrey Plaza to-do list? Opening her next motion picture next February.

The 27-year-old half-Puerto Rican actress/comedian—who recently picked up a Young Hollywood Award for her breakthrough performance in Safety Not Guaranteed—will be starring as a high school student working her way through the pains of social and sexual awkwardness in The To Do List.

In this first look at the 1990s-set comedy, it’s clear that both the film’s fashions and intended discomfort deliver a whole world of nostalgic pain.

The film, written and directed by Funny or Die‘s Maggie Carey, featured Plaza in 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.”

Along with the Parks and Recreation star, the film stars several comedy stars, including Donald Glover, Andy Samberg and Bill Hader.

The To Do List will hit theaters on Valentine’s Day 2013.