As plenty of sex comedies have proved, sex acts can be hilarious when attempted by the inexperienced. The awkwardness is overwhelming, and the trick is to find the comedy rather than just making the audience uncomfortable at watching a teenager fumble through dry humping. The To Do List follows its close relative American Pie in pressuring its uptight protagonist to achieve sexual adequacy, but the “twist” is that the teenager is a woman because hey! Women want sex too! Despite writer-director Maggie Carey providing a welcome gender swap for the genre, the picture is surprisingly tame until it occasionally manages a sneak attack with some of the most shocking gross-out gags in recent memory. Unfortunately, the overbearing 90’s setting and an unfortunately miscast Aubrey Plaza undermine the sympathy we’re supposed to feel towards our protagonist.
Brandy Klark (Plaza) is a Type-A personality who has managed to dominate her studies, but at the expense of the natural sexual education most teenagers discover in high school. When she has an accidental and clumsy encounter with the hunky Rusty Waters (Scott Porter), Brandy realizes the extent of her sexual inexperience and resolves to learn a variety of sex acts throughout the summer before she goes off the college. She makes a “to do” list compromised of sex acts she wants to do, and discovers that none of them are as easy as they seem.
From there, the plot meanders about as Brandy uses her friend Cameron (Johnny Simmons), who has a crush on her, for some of the acts; she also occasionally receives the council of her sexually explicit friends Fiona (Alia Shawkat) and Wendy (Sarah Steele), her obnoxious sister Amber (Rachel Bilson), and their kindly mother (Connie Britton). Meanwhile, Brandy works as a lifeguard in order to catch the eye of Rusty, and ends up developing an unlikely friendship with the pool manager, Willy (Bill Hader). Rather than having Brady use her sex list as a plot guide, the script just bounces the character about and hopes to find some laughs along the way.
And it does, but rarely in a rewarding fashion. Most of the humor stems from Brandy’s naivety, but that attitude is constantly running up against her bossy nature. She can give a hand job to Cameron in a movie theater, but she does it with all the enthusiasm of someone in the middle of taking a test. It fits her personality, and it’s amusing to see Cameron’s orgasm disrupt the other moviegoers, but Brandy’s bossiness defuses the humor. To be fair, her lack of enthusiasm is partially due to the fact that most of the items on her list are acts to perform on others rather than be performed on her, but the sexual mishaps only seem to come (no pun intended) at the end of each climax.
When these mishaps do happen, the film succeeds because its (perhaps unintentionally) lulled us into a false sense of security. Brandy’s going to have a sexually explicit conversation or lose her swimsuit top in the pool, but these aren’t particularly shocking antics. Then almost out of nowhere, Carey will hit us with a gross-out gag we didn’t think she’d go for because the movie has been playing it so safe. I won’t spoil these jokes, but they’re a welcome burst of life in a movie where the strong supporting cast gets an occasional laugh, but Plaza can only bring the uptight side of Brandy. She rarely garners our sympathy for the ambitious but unenthusiastic high-achiever.
Furthermore, she’s made smaller by the setting and the themes. The To Do List drips in 90’s nostalgia, and the script requires that the story can’t take place in a time where Brandy could access the Internet to find out the meaning of slang terms like “pearl neckless” and “motorboating” (how she came to these terms in the first place is never explained). However, the 90’s fashion and technology only highlights Brandy’s lack of color. She stands out as much as her Trapper Keeper.
The theme of societal repression of female sexuality is somewhat more rewarding. Perhaps I’m old-fashioned, but the frank sexual language from Fiona and Wendy occasionally startled me. The language didn’t bother me, but it provided a potent reminder that men dominate this genre, and yet people don’t bat an eye when male characters openly discuss their sexual escapades. I’ll also admit that since I’m a man, these talks were no stranger to my life during my teenage years. The To Do List seizes on the fact that men are more protective of female chastity but at the same time crave sex. For women, they have to worry about being labeled a slut, and The To Do List tries to navigate this double-standard by positioning Brandy as someone who’s not aiming to enjoy sex but to study it. Unfortunately, the pay-off on this fresh angle doesn’t amount to more than Brandy actually announcing what she’s learned from her experiences.
The To Do List always feels like it’s teetering on the edge of being a balls-out (or is it vag-out? Again: old-fashioned) teenage sex comedy. It wants us to sympathize with Brandy, but her personality keeps us at a distance. It wants to tread new ground with its jokes (and occasionally finds some great ones), but most would be at home in a PG-13 film. It wants to consider sexual coming-of-age from a woman’s perspective, but can only sort itself out to bring the theme to the level of an after-school special for older audiences. Sexual discovery and the comedy that can come from it imply a sense of freedom, but The To Do List is always hesitant to go all the way.