"The To Do List" is the newest addition to the "raunchy teen sex comedy" genre, and one of the few films in that genre to follow a girl's journey to losing her v-card (yes, we're calling it that). These movies love to point out everything that's awkward and disturbing about having sex for the first time.
We saw Jason Biggs hump a pastry in "American Pie", DJ Qualls upgrading from his dog and a jar of peanut butter ("Because it's your dog") to a woman roughly 8x his size in "Roadtrip", and Michael Cera getting vomited on in "Superbad". But in "The To Do List", (SPOILER!) director Maggie Carey does the unthinkable: the protagonist loses her virginity to the wrong guy (read: a douchebag) without any guilt/regret/mishap … and the world doesn't end.
Plaza's character, Brandy Klark, is the class valedictorian, a grammar-enthusiast, and everything else that character stereotype is in teen movies. She makes a to-do list of all the sexual acts she wants to master in order to appear sexually experienced to guitar-playing college babe (and awesomely named) Rusty Waters.
The movie itself wasn't great, although it did have potential. The story was good, the casting was great, and the '90s nostalgia capitalized perfectly on today's incessant Buzzfeed tamgotchi, slap bracelet, and pog heavy lists. But all the characters, except for Plaza's, felt flat. Carey, who also wrote the script of "The To Do List",: didn't take full advantage of Bill Hader's (who plays Plaza's boss) genius, instead limiting him to jokes about Plaza's chest, or lack thereof. Alia Shawkat (Maeby from Arrested Development) and Sarah Steele play Plaza's best friends, but they felt more like an empty sexual sounding board. And Rachel Bilson plays Brandy's promiscuous sister, who seems interested in only screaming rote insults at Plaza.
But this is all saved by what the movie did absolutely right: it showed a "good girl" doing "bad things" without judgment. (Feminists = 1 Other People = 0).
Brandy's journey through movie theater butter-lubed handjobs, "fingerbangs" under her denim skort, dryhumps with Christopher Mintz-Plasse (AKA McLovin), and being walked in on while giving her pillow some hot hip action, are all wonderfully uncomfortable (I saw the movie with six girls and we were all covering our gasps throughout each scene), but you can't help but feel for her. Girl is just trying to understand what all the fuss is about … at a time when you couldn't Ask Jeeves: "How do you make sex on somebody?"
So, despite its shortcomings, the movie hits the mark with its honest portrayal of female sexual curiosity. And to top it off, it breaks from the norm with her choice of v-card taker.
Brandy ends up having sex with the hot guy (our friend Rusty), as opposed to Cameron, the nice guy who has "true feelings" for her. And even after losing her virginity (in 30 "steamy" seconds) to Rusty, she tells both love interests that she has no regrets. She doesn't regret passing on Cameron, because she's 18 and "regrets are for your 30s", and she doesn't regret losing it to Rusty, because it's going to make a great story to tell her friends.