The 10 Most Awkward Virgins On Film

To celebrate the 10th anniversary of Judd Apatow's blockbuster hit The 40-Year-Old Virgin


    Being a virgin is hard, and Hollywood’s not helping. If two people in a movie aren’t fucking, it’s probably because they’re related. On celluloid, sex is easy, wild, and overflowing with orgasms. That’s why the release of The 40-Year-Old Virgin 10 years ago caught everybody’s attention: an adult male protagonist who isn’t banging every 21-year-old in sight? What is this sorcery?!

    It helped that The 40-Year-Old Virgin was really funny and oddly sweet. It didn’t judge Steve Carrell’s Andy, but instead balanced his zany journey between the sheets with honesty and tenderness. Of course, Andy wasn’t the first virgin to grace the silver screen. Unfortunately, many of those characters were often defined by their virginity in ways that stigmatized the very act of celibacy. Some films got it right, though, capturing the excitement and fear that accompanies your first time, which is, more often than not, an awkward affair.

    Here, we’ve compiled some of the awkwardest, the characters for whom sex was a mystery that could only be approached with a certain level of curiosity, distrust, and, in some cases, goofiness.


    For better or worse, we’ll always remember our first time. These characters sure will.

    –Randall Colburn
    Senior Staff Writer

    Cute Awkward

    william miller 2

    The Movie: Almost Famous (2000)

    The Virgin: William Miller

    What Made It Awkward? “Let’s deflower the kid.”

    Yes, the groupie deflowering of 15-year-old William (Patrick Fugit) is a bit uncomfortable, both because of the character’s tender age and the actor, who was 18 at the time, possessing a natural baby face. But what makes this scene more cute-awkward than creepy-awkward is that William, though stunned, is clearly receptive to the idea, and also that the object of his affections, Penny Lane (Kate Hudson) does not participate. Problems with her Manic Pixie Dream Girl character aside, Hudson cracking a smile and awkwardly peeking through her fingers makes her, in that moment, the audience’s older and wiser avatar (Aw, but he is so young and innocent!), and she leaves the room at the same time that we do, presumably to respect William’s privacy, i.e. his “coming of age” in more ways than one.

    Did He Get Laid? A strongly implied yes.

    The Deflowering (Or Lack Thereof):

    Leah Pickett

    Desperate Awkward

    The Movie: Welcome to the Dollhouse (1995)

    The Virgin: Dawn Wiener

    What Made It Awkward? Her age, for one. Dawn is only 11, and, as played by the pitch-perfect Heather Matarazzo, deeply uncomfortable in her own skin. Her attempts to seduce a sexy high school senior – whilst wearing footie pajamas, no less – are naive and almost sweet, but it’s her relationship with burnout bully Brandon that articulates the confusion and desperation at the heart of Dawn’s desire. When Brandon, the most prominent in Dawn’s sea of aggressors, tells her to meet him after school so he can rape her, Dawn actually shows up. Neglected at home and rejected by their peers, both Dawn and Brandon see sex as a tangible representation of the love they can’t find elsewhere. Young and confused, Dawn just wants to feel desired, no matter the circumstances.

    Did She Get Laid? Nope. Brandon’s threat just masked his own insecurity, and all they do is kiss. Dawn and Brandon form a flimsy courtship in the aftermath, but he runs away before they can seal the deal. Our last glimpse of Dawn is on a bus to Walt Disney World, surrounded by girls and hopelessly trapped in an adolescence she longs to escape. Director Todd Solandz’s Palindromes revealed Dawn died alone and miserable, but his forthcoming revisionist Welcome to the Dollhouse sequel might give us a kinder glimpse at her adult years.

    The Deflowering (Or Lack Thereof):

    Randall Colburn

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