The scene opens with her looking right into the camera, giggling like a kid.

Cut to him staring straight back at her, also giggling. He rubs his eye. He’s a kid, too.

“I like you so much,” she says.

“I like you,” he responds.

“Should we … take our shirts off?” she suggests with a certain sweetness.

He removes his and then it’s her turn.

“Don’t laugh at me,” she says. And when it’s off and he smiles she feigns upset. “Stop, no, you promised! Don’t say anything.”

“Are you kidding me? No, that’s … awesome,” he replies.

She crosses her arms in shy self-defense. Slowly, he reaches out and uncrosses them. They kiss.

“No, that’s awesome” is a very teenage way to react to a girl that has just stripped down to her bra, but The Spectacular Now is a film that’s built on the realism of its script. In the scene above, Sutter (Miles Teller) has reached the point in his relationship with Aimee (Shailene Woodley) when it’s time for the two teens to go all the way. But this is her first time. So they go slow. Nervous, uncertain and youthful, she follows him to one of life’s most famous checkpoints.

The loss of virginity has long been an event heavily covered in the arts, especially film. Whether literally or metaphorically, it shows up in some of the best movies about youth, and especially young love, ever created. Sofia Coppola’s The Virgin Suicides. The Last Picture Show. Blue is the Warmest Color. The Notebook. These movies are all about different things but they use first-time sex to develop their characters and also attempt to capture one of humanity’s most delicate experiences.

But the inherent nature of having sex for the first time makes scenes that try to depict it some of the most mismanaged in the history of the industry. While many people have included it, few (such as The Spectacular Now) have really been able to do it in a way that’s not terrible.

There are two ways movies often get this scene wrong. Mostly in comedies, you have the clueless male trope (“I put what in the what?!?”). Dorky, horny and desperate, he is a cartoonish version of what the world believes many boys are like when first getting down to business. Think American Pie, Superbad or The 40-Year-Old Virgin. There is often a joke or jokes made in scenes about trouble (or too much ease) getting it up or how long the sex lasts. He often apologizes afterward, especially if things go drastically (read: hilariously) wrong.

This portrayal often falls flat because the event itself is too personal. Yes, sex is probably something that society takes too seriously but most people view their first time as something special. To paint it in such a farcical light does nothing for an audience that has probably already lived through a first time that was pretty awkward. This type of scene also loses points in its ridiculous depiction of the male first-timer. Not every teenage guy is some clumsy meathead on the hunt for someone to take his V-card. The personal nature of losing your virginity is what stands in the way of movies really being able to use it as a laugh catalyst.

On the other end of the spectrum, some movies go for a cinematic, stylized look that isn’t realistic. Young people, or virgins of any age, do not have passionate, choreographed, near-perfect sex. Just not how it works. But some filmmakers, to appeal to an audience’s hunger for nudity or sexual content, amp up the hotness in a scene of first contact.

Think of Ryan Phillippe and Reese Witherspoon getting it on in Cruel Intentions. Was your first time a beautifully lit, sensual blend of bodies like theirs was? While this type of scene gets at the intimacy and personal nature of losing your virginity that the comedy example doesn’t go near, it ultimately fails in its lack of imperfections. The experience is too real to not depict it realistically.

Losing your virginity is such an elusive, complex occurrence that even a medium as deep and nuanced as film can’t exactly peg it — the lead-up, the tension, the anxiety, the dynamic of the relationship, the act itself. And that’s not even mentioning how some viewers sink into their seats with awkwardness at any sex scene, let alone one that involves a virgin or two. Not many movies get things as close to right as The Spectacular Now, so it’s uncharted waters. Just like a virgin, the artist must try to figure things out as they go. While the results may be special to them, they are typically disappointing.