The sex comedy is a difficult genre to get right. For the most part, it's been dominated and perfected by male leads and writers. Unfortunately, Maggie Carey’s writing and directorial debut, The To-Do List, does not serve to vindicate this genre for women. Every so often, it also seems necessary to release a comedy set in a different decade—you know, so you can make fun of how quaint it seems in retrospect (e.g The Wedding Singer). Thus, The To-Do List takes place in the Boise, Idaho of 1993.
The story follows the virginal life of senior valedictorian Brandy Klark (Aubrey Plaza), whose feelings of sexual inadequacy begin to mount after her friends, Fiona (Alia Shawkat) and Wendy (Sarah Steele), take her—against her will—to a post-graduation party where she encounters Rusty Waters (Scott Porter), a decidedly douche bag type with a Zach Morris aesthetic. So enraptured by his mere presence (which also devolves into an uncomfortable fantasy wherein everyone else disappears from the room, leaving Rusty to serenade her a terrible version of “Pour Some Sugar on Me”), Brandy can’t help but get extremely drunk to cope with her emotions. Before the end of the night, Fiona and Wendy have to escort her into an empty bedroom to pass out. Rusty, thinking she’s someone else even though it’s not even that dark (because he’s just that dense), starts to make out with her, but Brandy is so awkward that she ends up blurting something about herpes. This prompts Rusty to realize she’s not who he thought she was and quickly leave the room.
Humiliated by her inexperience, Brandy vows to make up for lost sexual time over the summer. Consulting with her older, much sluttier sister, Amber (Rachel Bilson), Brandy compiles a list of all the acts she must complete before giving herself to Rusty. Her nerd status, however, makes it difficult for her to attract interest from the opposite sex—save for her best friend and chemistry lab partner, Cameron (Johnny Simmons, whose best role will always be as Chip in Jennifer’s Body).
Unluckily for Cameron, Brandy only sees him as a means to gain experience and nothing more. He doesn’t recognize this fact until after screaming “I love you” in a movie theater (to see The Firm) in the wake of getting a hand job from Brandy. Surprised to find her Trapper Keeper filled with sexual notes and her to-do list, Cameron hurls Brandy with insults, exclaiming, “I hope you get AIDS!” This sends Brandy right into the arms of Cameron’s best friend, Duffy (Christopher Mintz-Plasse a.k.a. McLovin in his usual role)—allowing her to check dry humping off the list.
Her sexual frenzy continues with fellow lifeguard Derrick (Donald Glover, who seems to have chosen a forgettable part). Derrick offers to eat her out so that he can learn how to better satisfy a woman. Pretty soon, Brandy’s reputation begins to precede her, particularly when Willy (Bill Hader), her drunken boss, catches her giving head in the shower of the pool’s locker room. Although The To-Do List is clearly intended to empower and affirm female self-reliance—one of Brandy’s repeated phrases is “A woman needs a man like a fish needs a bicycle”—it ends up coming across as a series of mixed messages. Not wanting to settle entirely on the theme of “sex is meaningless,” Carey waffles on the point by essentially saying “sex may or may not be meaningless, so just sleep around in the interim.” And it is this vacillation that takes away from The To-Do List, highlighting the fact that it is a feature film virgin’s (full-circle, you see?) project.
The film’s attempt to take the best elements of classic plotlines like Porky’s, Revenge of the Nerds and Say Anything (all 80s movies, it should be noted—though the early 90s did still have the aesthetic uncertainty of its preceding decade) and mash them up to revamp the sex comedy genre ultimately falls short. Moreover, it's a huge step down for Plaza from the amazingness that is Safety Not Guaranteed. And so, until someone like Sofia Coppola or Zoe Cassavetes tries her hand at this style, I’m afraid women will have to be saddled with Seth Rogen and Judd Apatow for their sex comedy fix.