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Hellin Kay

Photo: Courtesy of Quat'sous Films; Everett Collection

Shailene Woodley, who once again loses her virginity in Gregg Araki's latest film, White Bird in a Blizzard, recently confessed that it's her awkwardness that lends an air of authenticity to those performances. (I don't remember anything awkward about the way she handles Sutter Keely in The Spectacular Now, but hey, that's just me!) But what about other memorable cinematic portrayals of characters' first times? From the triumphant to the tragic, here are eight of the very best V-card checkout scenes:

1. The Best Voyeuristic Loss of Virginity: Cruel Intentions (1999)
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Ryan Phillippe famously vomited after filming the fight during which his dirty bird Sebastian dumps good girl Annette (then-fiancée Reese Witherspoon). But in this beautifully lit scene, in which the two finally consummate their relationship after the best escalator moment of all time, is a glorious mélange of mouths, peachy skin, and heaving breasts. All to the sound of Adam Duritz's voice.

2. The Best Nerd-Gets-the-Girl Loss of Virginity Post-Coital Recap: Sixteen Candles (1984)
[THE SCENE: her hot soon-to-be-ex-boyfriend's-dad's car]:

Freshman Geek: Did We, uh…?

Gorgeous Senior: Yeah…I'm pretty sure.

Freshman Geek: Um, excuse me, but, um, do you know if, did I enjoy it? What am I, nuts? Of course I enjoyed it. What I meant was um, did you?

Gorgeous Senior: Hm. You know? I have this weird feeling I did.

3. The Best High School Sweethearts Loss of Virginity: Love & Basketball (2000)

It's hard to say who Monica Wright (Sanaa Lathan) loves more: Quincy "Q" McCall (Omar Epps) or Spalding. (That's an in-joke for L&B groupies, who know how hurt Monica was when Q accepted Shawnee Easton's invitation to the school dance.) But fear not, friends, because soon enough, these two next-door neighbors (slash soulmates) are getting down with some safe sex to the sweet sounds of Maxwell's version of "This Woman's Work." And it's divine.

4. The Best Power-of-Omission Loss of Virginity: Clueless (1995)

One accidental joyride on the freeway and Dionne (the inimitable Stacey Dash) and Murray's (Donald Faison) mutual virginity goes from "technical" to "nonexistent." Well played, Murray. Well played, indeed.

5. The Best I'm-Scared-by-Love Loss of Virginity: Blue Is the Warmest Color (2013)

The film's lengthy (and physically rigorous) sex scene was analyzed ad nauseam by critics and talent alike, but the budding young love between Adèle (Adèle Exarchopoulos) and Emma (Léa Seydoux) is one of the most tender cinematic portrayals of what it's like to give yourself fully to another human being—and what it's like to lose yourself in someone else—in film history. (If you don't believe me, watch the diner breakup scene. That is love lost, people.)

6. The Best Post-Virginity Taking Pride Womp: Can't Hardly Wait (1998)

This cult-loved classic about an epic rager on the last night of high school has so many memorable moments—"Hey yo, Kareem baby! What's up???"; "Aman-duh"; "I saw no third dimension"—but the moment after Kenny Fisher (Seth Green) and Denise Fleming (Lauren Ambrose) finally give in to their school-age-turned-teenaged crushes, and she utters those brutal words: "Next time, you know, you won't be…it can go for…longer," boys everywhere felt Special K's special brand of embarrassment.

7. The Best Post-Loss-of-Virginity Doodle: The Fault in Our Stars (2014)
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Hellin Kay

Augustus Waters (Ansel Elgort) may be a boy with one leg, but after he and Hazel Grace Lancaster (Shailene Woodley) do the deed in Amsterdam, he belongs to a much smaller contingent: boys with one leg who have also had sex. It's sweet. And funny. And heartbreakingly sad.

8. The Best This-Won't-End-Well Loss of Virginity: Fear (1996)

Sure, David (Mark Wahlberg) exhibited some grade-A creepster behavior—punching Gary at school, playing billiards in a wet suit—but there's something so satisfyingly sexy when he and Nicole (Reese Witherspoon), whose parents are conveniently out of town at a James Taylor concert, finally go all the way. (Plus: After that roller coaster scene, we'd all probably die a cruel, cruel death if those two didn't do the hibbidy dibs, you know?)