The To Do List

I vividly remember the first time I saw the trailer for The To Do List. It felt like a glitch in the Matrix—a teen sex comedy where the protagonist wasn’t a desperate nerd trying to lose his virginity before prom, but a high-achieving, slightly terrifying valedictorian who approached sexual experimentation with the same cold, calculated intensity I usually reserve for filing my taxes. Watching it again recently, I realized that Aubrey Plaza was the only person on the planet who could have made this character work.

I watched this while sipping on a lukewarm ginger ale that had lost its fizz twenty minutes earlier, which honestly felt like the perfect beverage pairing for a movie about fizzled expectations and the flat-out awkwardness of being eighteen.

The Clinical Approach to Climax

Set in 1993, the film follows Brandy Klark (Aubrey Plaza), a girl who has spent her entire life winning. She has the grades, the extracurriculars, and a permanent scowl that suggests she finds your lack of a five-year plan offensive. But after a brush with the local "hot guy" and college legend Rusty Waters (Scott Porter), Brandy realizes she’s entering the Ivy League with a severe deficit in "life experience." Her solution? A literal, handwritten list of sexual milestones to achieve before the summer ends.

What I love about the script by writer-director Maggie Carey is how it treats sex not as a magical, moonlit event, but as a series of chores to be managed. Brandy doesn't want "love"; she wants the credits. There’s something deeply funny—and, if I’m being honest, relatable—about a person trying to intellectualize their way through a blowjob. Brandy Klark is essentially a sociopath with a highlighter, and that’s why she’s the perfect protagonist. She approaches the "hand job" box on her list with the same grim determination a soldier might use to clear a minefield.

A Murderer’s Row of Comedy

While Plaza is the anchor, the supporting cast is a staggering "who’s who" of 2013 comedy excellence. You’ve got Bill Hader as Willy, the world’s most disgruntled pool manager, who seems to exist entirely on a diet of sarcasm and chlorine. Hader, who was married to director Maggie Carey at the time, plays the "mentor" role with a wonderful, low-stakes laziness.

Then there’s the friend group: Alia Shawkat and Sarah Steele provide the necessary groundedness, acting as the audience’s proxy for every time we want to scream, "Brandy, what are you doing?" The film also manages to sneak in Donald Glover, Andy Samberg, and Connie Britton (as Brandy’s surprisingly sex-positive mom).

But the standout for me is Johnny Simmons as Cameron, the "nice guy" who is clearly in love with Brandy. In most movies, he’d be the hero. Here, he’s a casualty of Brandy’s checklist. Their chemistry is fueled by a mutual, crushing awkwardness that felt so real it made my teeth ache. The movie is secretly a horror film for anyone who actually remembers the crushing awkwardness of their first time.

The Low-Fi Indie Charm

Looking back from our current era of $200 million streaming "content," The To Do List feels like a relic of a very specific indie boom. Produced for a lean $1.5 million, it’s a masterclass in making a small budget look like a deliberate aesthetic choice. Carey shot the film in just 24 days, mostly in and around a community pool in Van Nuys, California. Because they couldn’t afford massive period-accurate sets, the 90s nostalgia is handled through small, tactile details: Trapper Keepers, cassette tapes, and the sheer horror of high-waisted denim. The 90s nostalgia here is better than 'Stranger Things' because it remembers how ugly the clothes actually were.

The film’s "Indie" DNA shows up in its willingness to be genuinely gross. It doesn't have the polished, "everyone is a model" sheen of a studio rom-com. It’s sweaty, it’s messy, and it features a running gag involving a "poop in the pool" that is handled with more cinematic suspense than most modern thrillers.

The trivia behind the scenes is just as charmingly low-key. Most of the cast members were friends from the Upright Citizens Brigade (UCB) scene, which explains why the improvisational timing feels so tight. Apparently, the crew had to constantly fight the Southern California sun to keep the "1993" vibe consistent, and many of the background actors were just locals who happened to be at the pool that day. It’s a film made with favors and grit, and that scrappiness translates into the humor.

The To Do List is a sharp, foul-mouthed subversion of the teen genre that holds up surprisingly well a decade later. It manages to be a period piece without being a "nostalgia trap," focusing instead on the universal, timeless embarrassment of trying to grow up too fast. It’s not a "perfect" movie—some of the subplots feel a bit thin—but it’s a riotous showcase for Aubrey Plaza's unique brand of deadpan chaos. If you’ve ever tried to plan your way out of an awkward situation only to make it ten times worse, this one is for you.