For every movie about a guy’s quest to lose his virginity, there’s a girl’s story left untold — but The To Do List has that on the top of its list to remedy. Our heroine, Brandy Klark, played with much aplomb by Aubrey Plaza, is her graduating high school class’ valedictorian, but she has a singular goal to achieve before she starts college — and it’s to sleep with hot older guy about town Rusty Waters (played by Scott Porter). Since she’s a virgin, her plan is to get some experience under her belt first, so she makes a checklist of every sexual practice she’s ever heard of, with the goal to acquire skills she thinks it would be necessary to finally “graduate” in this arena.
“People said, ‘Aubrey’s too pretty. Guys would just sleep with her, no problem,'” the film’s writer/director Maggie Carey told IFC. “But she doesn’t want just any boy. She wants a hot college boy, and she has no way to wow him. She’s inarticulate in front of him.”
Brandy, however, is far from inarticulate in front of everybody else. She’s the quintessential high-achieving smart girl at school, who in any other movie or sitcom would be portrayed as a nerd, even if she’s a cute nerd. Think Carol Seavers on Growing Pains, Jesse on Saved by the Bell, Willow on Buffy the Vampire Slayer, Tracy Flick in Election, Hermione Granger in the Harry Potter series. Some of these girls are referenced visually in the film, which takes place in 1993, since the costume designer actually tracked down wardrobe items from Saved by the Bell and Beverly Hills, 90210. “When Rachel Bilson shows up at the pool with a great black and white print with the midriff showing, that was something Donna would have worn,” Carey said.
Although these girls did sometimes get the hot guy (or hot girl, in Willow’s case), they usually had some degree of romantic feeling about it. The ones who were a little more cynical about it — Stacy in Fast Times at Ridgemont High, Ferris and Angel in Little Darlings — had to pay a price of sorts for their nonchalance.”One thing that was very important to me is that losing it wasn’t a bad thing,” Carey said. “I didn’t want Brandy to regret it. It didn’t happen as she thought it would, or the way she expected it would, but she was in control. The audience never had to be worried for her, so you’re not uncomfortable.”
Some of Brandy’s first experiences with making out, digital stimulation, and hand jobs are with her male study partner Cameron (played by Johnny Simmons). From his perspective, this constitutes a romance, but not in Brandy’s eyes.
“That was something that even when I was trying to get the movie financed, marketed, and tested, people kept calling it a romantic comedy,” Carey laughed. “But this is not romantic! This is a comedy comedy, not a romantic comedy. Don’t get me wrong. I love romantic comedies, but that’s not what this is. Brandy is stereotypically male, and Cameron is stereotypically female, because he’s sappy about it, and she’s more methodical, treating sex like she’s studying for a test.”
Hence her penchant for wanting to get the terminology right. A funny discussion between Brandy’s friends (played by Alia Shawkat and Sarah Steele) is a debate about what to call a particular sex act, pre-Internet when you couldn’t look up sex slang on Google. “It’s the one most people kept asking me about, when I sent out a draft of the script for feedback,” Carey said. “Fingerbang. One person said, ‘No, I think it’s called, ‘Fingerblasted.’ Another would write back, ‘I think it’s fingerbombed.’ So I turned that into the argument in the movie.” (The term that confused Carey most growing up? “Pearl necklace. No one was doing it, but people would make jokes about it, and you’d be like, ‘What is that? What? No thank you!'”)
During one of these feedback sessions, Michael Cera came up with an alternate title for the film — The Fuck-It List. “That was a pretty brilliant title,” Carey chuckled. “We actually were going to call the film The Hand Job at one point, and then once we started location scouting at schools, we realized we couldn’t keep it.”