Even as this comedy strains to be goofy and transgressive, it catches us by surprise simply because it dares to explore first-time sexual experiences through female eyes. And Aubrey Plaza (Safety Not Guaranteed) brings her usual sardonic wit to the lead role, merrily offending the more timid moviegoers while making more adventurous fans wish the film went even further.
Plaza plays Brandy, who graduated at the top of her Boise high school class. But with that goal achieved, she wonders if she neglected to prepare properly for university social life, so she makes a summer to-do list of sex-related tasks leading, hopefully, to losing her virginity to the hunky guitar-strumming lifeguard Rusty (Porter). She works with him at the local swimming pool along with her nice-guy best pal Cameron (Simmons), who's of course secretly in love with her. But as Brandy works through the list with the help of her friends (Shawkat and Steele) and her experienced big sister (Bilson), she starts to worry that her emotions are getting in the way.
Thankfully, writer-director Carey refuses to let this turn into a romantic slush-fest, keeping the encounters jagged and often very funny. The script is packed with hilariously squirm-inducing conversations about sex, many involving Brandy's far too helpful mother (Britton). Although her dad (Gregg) and her loser boss (Hader) understandably don't want to know. Meanwhile, when the local guys (Glover and Mintz-Plasse) find out about Brandy's list, they are sure to tick off a few items themselves, as does a visiting rock star (Samberg).
Yes, all of this is very corny, but the underlying honesty about sexuality is refreshing, as the film playfully refuses make first-time sexual experiences into something earth-shattering. Indeed, the way Brandy approaches this as an academic task is very clever, as she doesn't take into account the intimacy involved. In the end, the film is both too cold and too nice for its own good. If filmmaker Carey had cut loose just a bit more, finding a sharper edge to what's essentially a nice comedy, this might have been an essential addition to the losing-your-virginity genre.