The To Do List's Radically Practical Message About Virginity

It's a good idea to wait for true love -- but if you don't, it's not the end of the world.

CBS Films

The To Do List may look and feel like an R-rated teen sex comedy in the modern tradition, a la American Pie or Superbad or The Girl Next Door -- and, true to form, it offers gross-out gags and F-bombs aplenty.

But at the center of writer/director Maggie Carey's brave, funny debut film, there's an un-panicked, radically reassuring portrayal of teenage sex.

Set in the summer of 1993, The To Do List follows late-blooming valedictorian Brandy Klark (Aubrey Plaza) as she attempts to master a full repertoire of sexual proficiencies with interchangeable male classmates. The end game to this plan: losing her virginity to chick-magnet lifeguard Rusty Waters (a delightfully '90s-tastic Scott Porter) before starting her freshman year at Georgetown. Her more experienced best friends (Alia Shawkat and Sarah Steele) counsel her along the way, while her dorky but endearing friend Cameron (Johnny Simmons) quietly pines for her.

What's unusual about The To Do List isn't that Brandy sets her sights on losing her virginity to a gorgeous, kinda-brain-dead older boy; pop culture boasts plenty of young women who initially just want to get the whole awkward rite of passage over with. Instead, what's unusual about Carey's film is that (spoiler alert) Brandy succeeds -- and then moves on. She loses her virginity to a guy who doesn't really know her and definitely doesn't love her, and then she checks off the "Intercourse" box on her eponymous to-do list, packs up her things, and goes to college, un-traumatized and un-stricken by tragic regret.

When it comes to teenage girls losing their virginity on TV and in the movies, a few old storylines tend to get recycled. Most of them have to do with the fear of what could happen if the girl doesn't "save it" for the right moment or the right guy. These fictional teenagers with plans to have sex for the first time often "come to their senses" at the last minute, or get effectively dissuaded by someone older and wiser who advocates waiting for the "right" guy to come along -- the good guy, the One, who's trustworthy and kind and loves her for the right reasons.

My So-Called Life's Angela Chase, for instance, backs out of losing her virginity to her longtime crush, the dopey but sexy Jordan Catalano, because she's simply not ready. Rachel Berry saves herself for Finn on Glee after thinking better of her promise to let bad-boy rival glee-club singer Jesse be her first. On Friday Night Lights, a determined Julie Taylor makes a curfew-conscious appointment to have sex for the first time with her new boyfriend Matt Saracen -- only to get nervous and realize that, like her mother warned her, she's not ready. (Julie and Matt do have sex later -- after it's been firmly established over the course of a season or so that Matt is, indeed, the "right" guy.)

On How I Met Your Mother, Robin Scherbatsky realizes her younger sister Katie has plans to have sex with her obnoxious boyfriend when they visit New York together; she enlists her friends to help talk her out of it, and they succeed. American Beauty and What Women Want feature father figures persuading teenage girls away from having sex for the first time with men who don't love them. In 2002's Crossroads, Britney Spears's valedictorian Lucy reneges at the last minute on a pact to lose her virginity with her high-school lab partner, and instead has sex for the first time with Ben, a sensitive musician who once rescued his sister from their abusive dad.

And what happens to the fictional teenage girl who actually goes through with it, who loses her virginity without waiting for a boy or man who loves her truly, madly, deeply, and honestly?

Very bad things, frequently. Sometimes it's immediate karmic retribution: Marissa Cooper from The O.C. "finally" gives in to her jerky boyfriend of several years only to find out soon afterward that he's been habitually cheating. The Virgin Suicides' Lux Lisbon has sex with the school heartthrob on a football field only to fall asleep afterward, get abandoned, break curfew, and subsequently get put under parent-inflicted house arrest for what's effectively the rest of her life. Sometimes it's pregnancy: Juno of Juno, Mary Cummings of Saved!, and Becky Sproles of Friday Night Lights all find themselves pregnant after their first time. And still other times it's paralyzing regret, like Felicity on Felicity. As a 1999 Entertainment Weekly review put it when describing her post-sex antics: "You could read the guilt-stricken reaction all over Russell's face ... she looked ashen throughout the episode."

The To Do List, though, presents a less common kind of story about a girl having sex for the first time. Brandy loses her virginity to Rusty -- who's clearly not the guy she's "meant to be with" -- then has a moment of thoughtfulness before meeting up with her best friends right in time to announce her recent banging of Rusty Waters and then catch the rest of Beaches. When Brandy's dad (a hilariously anal-retentive Clark Gregg) discovers what's happened and races to her rescue, a calm Brandy reassures him, "I'm fine, Dad. I'm OK."

By sidestepping the "emotional-trauma-after-virginity-loss" construct and replacing it with giddy detail-spilling among friends, The To Do List sends up both a female onscreen teen-virginity trope and a male one: The "late-blooming virgin loses it to generically hot rando, comes away with high-five-worthy story to tell buddies" theme crops up more often in stories about teenage boys. (See: American Pie, Sixteen Candles, Almost Famous, Porky's, Road Trip, Losin' It -- and Superbad, kinda.) And perhaps more importantly, it provides a positive alternative outlook on what happens to girls who "give away their flower" or don't "guard their carnal treasure": Sometimes, they're pretty much fine.

It's not that waiting for the "right" sexual partner is a bad idea to promote among teenage audiences. Waiting for the right sexual partner is a really, really good idea. That's both for health and safety reasons, and because we can probably all agree that sex is most magical, the first time and every time, when it's between two people who are mutually trusting and nuts about each other.

And, to its credit, The To Do List seems to recognize this. Near the end of the film, Brandy finds herself face-to-face with both Rusty (with whom Brandy's just had a mildly disappointing first sexual encounter) and Cameron (who's hurt and angry that Brandy has broken his heart, used him and his friends as hookup practice partners, and slept with Rusty). Finally, she realizes Cameron is sweet, reliable, thoughtful, and the kind of guy she should have been with all along, and she tells him so.

But then: "I don't regret it," she tells him. "I'm a teenager. I'll have regrets when I'm... 30.

"And you," she says to Rusty, "are -- really hot." Does she wish she hadn't lost her virginity to him? "No. Because you are going to make an awesome story to tell my friends."

At the end of the film, Brandy is pictured a few months into her freshman year at Georgetown -- where she's well-adjusted, involved on campus, making friends, and having great sex with a guy who likes her.

Advertising to teens that they'll be perfectly fine after doing what Brandy does is, of course, a slippery slope at best. Care and caution are always a wise choice in real life. But the "hold-out-and-then-have-consensual-safe-sex-with-the-right-guy-or­-else" narrative often omits the fact that if a teenage girl happens to hold out and then have consensual, safe sex with the wrong guy, it's OK for her to simply accept it and move forward, sans the seemingly obligatory emotional baggage.

Taken as a whole, The To Do List functions as a sort of Everybody Poops for the world of sex. Everybody does it: young people, old people (like Brandy's wonderfully warm, kooky parents, played by Gregg and Connie Britton), pretty people (like Brandy's older sister Amber, played by Rachel Bilson), icky people (like Brandy's pool-manager boss, played by Carey's husband Bill Hader). And it takes care to show that there's a diverse range of ways to experience sex. Sometimes it's a sacred pledge of deep emotional investment and mutual trust, as it seems to be between Brandy's parents. But sometimes it's a transaction, sometimes it's a pastime, and other times it's simply a haphazard, non-committal muddle of fluids and sweaty limbs. The memorable message of The To Do List is that, as Brandy muses in the final scene, "Sometimes sex is just sex" -- and whether or not you've had it doesn't have to change who you are.