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The 10 Most Awkward Virgins On Film

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

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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

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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

Spooky Awkward

Film Title: Fear

The Movie: Fear (1996)

The Virgin: Nicole Walker

What Made It Awkward? Fear is one of those “romance thrillers” that lays all of its cards on the table before you watch it. A brief skim of the synopsis (“When Nicole met David, he was everything … but soon she sees that David has a darker side…”), or, heck, even a glance at the creepy poster (tagline: “Together forever. Or else.”) tells you everything you need to know. Nicole: you in danger, girl. It all starts when Nicole (Reese Witherspoon, perennial player of virgins throughout the ‘90s) meets David (Mark Wahlberg) at a rave. He seems perfect, at first: handsome, charming, thoughtful, affectionate, and unafraid to share his feelings. It is only a matter of time before they bone.

Did She Get Laid? Unfortunately, yes. David fingers Nicole on a rollercoaster, kisses her with way too much tongue, and says her virginity is something to “admire and respect” as a prelude to getting her in bed. Sex her up in the sheets he does, and the awkwardness of the scene is fully dependent on the fact that we know this creepo David is going to make Nicole’s life a living hell after this. Nicole having sex with David is the equivalent of a girl in a horror movie walking outside, alone, to investigate a strange noise. (“No, don’t, stop!” the audience moans.) Although to Nicole’s credit, if she had known that David would carve “Nicole 4 Eva” into his chest, like the next day, that alone might have kept her from doing the deed. But then we wouldn’t have the ‘90s camp classic that is Fear, which I’m proud to say that I rented from my local Blockbuster in 1998.

The Deflowering (Or Lack Thereof):

Leah Pickett

Overcompensating Awkward

bclub3 The 10 Most Awkward Virgins On Film

The Movie: The Breakfast Club (1985)

The Virgin: Brian Johnson

What Made It Awkward? Niagara Falls. Or, rather, Brian’s clearly fabricated story about getting it on with a girl at Niagara Falls. “I’ve been laid lots of times,” Brian lamely asserts, and anybody who’s ever felt self-conscious about their lack of intimacy can relate. What I love about Brian’s story and Anthony Michael Hall’s delivery is that I believe it … to an extent. He probably did meet a girl at Niagara Falls, and maybe they, like, kissed, ya know? But that’s not good enough in high school. And, for that reason, most high schoolers lie about sex, whether it’s about having it or how good it was.

Did He Get Laid? Of course not, they’re in detention. But I like to think Brian, like so many of us, eventually came into his own once he went off to college.

The Deflowering (Or Lack Thereof):

Randall Colburn

Skeevy Awkward

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The Movie: Kids (1995)

The Virgin: The impossibly young girl in the opening scene.

What Made It Awkward? Ah, where to begin. One could start with the fact that 16-year-old Telly (Leo Fitzpatrick) is guppy-macking on a 12-year-old girl. Or that she seems scared and unsure about going through with the sex part, but Telly is fleecing her like a pro, grooming her with all of the sweet nothings in his arsenal, so that her virginity can become his prize. Or that the bedroom in which their nubile, half-naked bodies writhe looks like that of a typical 12-year-old girl — Laura Ashley bedding, stuffed animals on the dresser, a ballerina music box on the shelf — because, as I mentioned, the face that Telly is sucking is that of an actual child.

Did She Get Laid? Yes, and it is the stuff of nightmares.

This scene is even more chilling in hindsight, because later in the film, we find out that Telly is (spoiler alert) knowingly HIV positive, and yet he still pressured this girl, and who knows how many others, to have sex with him. Reckless does not even begin to describe his behavior; predatory is more like it.

Obviously, the opener was intended to shock — Kids is a cautionary tale of “kids these days” taken to the pearl-clutching extreme — but every minute detail of this scene, from the sweat beading on the girl’s forehead to the awfully loud, wet, and smacking sounds of their lips — is enough to make one’s skin crawl for years.

The Deflowering (Or Lack Thereof):

Leah Pickett

Gross Awkward

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The Movie: American Pie (1999)

The Virgin: Jim Levenstein

What Made It Awkward? Oh, so much. American Pie explores teen sexuality from a variety of angles (positions?), but it derives much of its comedy from the flailing efforts of Jason Biggs’ Jim Levenstein. Everything about his journey is exaggerated: Jim’s parents don’t just walk in on him masturbating, they dodder around as scrambly porn moans in the background; he doesn’t try masturbating with Vaseline or something, he sticks his dick in an apple pie; and when he gets the chance to sleep with a saucy foreign exchange student, he doesn’t just prematurely finish, he live-streams his humiliation to every inbox in the county. What American Pie gets right is that, for most teens, losing your virginity can be more gross than anything.

Did He Get Laid? Yes, to a mousy band geek he’d previously thought to be a snooze. She dominates him with ease, proving to Jim that in addition to being awkward and gross, sex can also be wildly unpredictable.

The Deflowering (Or Lack Thereof):

 

Randall Colburn

Sweet Awkward

spectacular now

The Movie: The Spectacular Now (2013)

The Virgin: Aimee Finicky

What Made It Awkward? This one is kind of a cheat, because the film never explicitly states that Aimee (Shailene Woodley) is a virgin. At 17, Aimee tells Sutter (Miles Teller) that she has never had a boyfriend. That, coupled with the “good girl who tames the bad boy” role that her character duly occupies and her tongue-tied insecurity in regards to her own sexuality (“Guys don’t look at me like that”) implies that Aimee is, at the very least, much less experienced than Sutter, the high school party boy and stud. In the book, Aimee refers to an untoward advancement by a 20-year-old when she was 14, but that backstory was cut from the film version, leaving the audience to presume that Sutter and Aimee’s “first time” will also be Aimee’s first ever.

One of the reasons The Spectacular Now was so warmly received by critics and audiences alike is the gawky naturalism of its leads, particularly in the lead-up to that inevitable love scene, which, in all of its realism, is almost unbearably acute. The foreplay is awkward — lots of giggling, fumbling, and whispers of “I like you so much” — but isn’t that how it usually goes?

Did She Get Laid? Sure did. And it goes to show how real-life sex, especially teenage sex, is never as glamorous as the movies make it out to be — no matter how many candles you light or how deftly you employ the seductive powers of Counting Crows’ “Colorblind” — and The Spectacular Now is wise to forgo the soft-lit, Cruel Intentions route, opting instead to use the poignancy of awkwardness to its advantage.

(For another sweet and awkward depiction of first-time sex, see The Fault in Our Stars, also with Woodley; she taps into a vulnerability that makes both scenes shine.)

The Deflowering (Or Lack Thereof):

–Leah Pickett

Religious Awkward

mermaids1 The 10 Most Awkward Virgins On Film

The Movie: Mermaids (1990)

The Virgin: Charlotte Flax

What Made It Awkward? Considering that Winona Ryder was dating Johnny Depp while filming Mermaids (Fun fact: Depp visited then 10-year-old Christina Ricci on the set and then went on to play her love interest nine years later in Sleepy Hollow … Hollywood), she does an excellent job playing a self-denying teenager who takes a vow of celibacy. Charlotte, the 15-year-old daughter of Rachel (Cher) and elder sister of Kate (Ricci), is a nun-in-training, even though her family is Jewish. She is vehemently opposed to sex; a little too vehemently, perhaps, as she starts fantasizing about Joe — a brunette facsimile of a Ken doll who also happens to be the caretaker of her local convent — from the moment her eyes meet the perfection of his bod. After kissing Joe in the convent’s clock tower, Charlotte resigns herself to fasting as a way to purge herself of her sinful thoughts, even going as far as to believe that God may have made her pregnant from the encounter, as punishment for being so “bad.”

Did They Get Laid? Hells yeah. Eventually, Charlotte gives into her perfectly natural desires and meets Joe in the clock tower for some intense, Harlequin romance-style sex — she shows up in her mother’s body-hugging polka dot dress; he rips it off in the throes of passion — but alas, they are awkwardly interrupted by the sounds of Charlotte’s sister drowning in a ravine.

I don’t think these two got to finish what they started, but it still counts.

The Deflowering (Or Lack Thereof):

Leah Pickett

Charming Awkward

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The Movie: Superbad (2007)

The Virgin: Evan

What Made It Awkward? Michael Cera, basically. Bringing the mumbly charm of George Michael Bluth to a character that’s just slightly less pathetic, Cera’s Evan can’t stop muttering awkward bon mots even as he’s being undressed by the object of his affections. Becca, the lady with whom he finds himself on the verge of coitus, is more confident but equally silly: “I am gonna give you the best blow-jay ever … with my mouth.” It’s dirty talk as interpreted by teenage virgins, and it’s as charming as it is awkward.

Did he get laid? Alllllmost, but Evan puts a stop to it, uncomfortable with the fact that they’re both schwasted. The film’s epilogue implies that romance still simmers, however, and there’s no doubt the two (soberly) swapped V-cards that summer.

The Deflowering (Or Lack Thereof):

Randall Colburn

Lit-the-Candle Awkward

hocus pocus 1993 The 10 Most Awkward Virgins On Film

The Movie: Hocus Pocus (1993)

The Virgin: Max Dennison

What made it awkward? Like most 16-year-old boys, Max (Omri Katz) is desperate to get laid. But when he tries to talk up pretty girl Allison (Vinessa Shaw) at her family’s Halloween party, his little sister Dani (Thora Birch) makes it awkward. “Max likes your yabbos,” Dani tells Allison. “In fact, he loves them.” Yabbos meaning boobs, I guess, although I’ve never heard that term in reference to anything. Has anyone heard the word “yabbos” outside of Hocus Pocus? Anyway, Dani is the ultimate cockblocker. So Max must convince Allison that he is worthy of being had.

They’re both into witches, so Max convinces Allison to accompany him to the old Sanderson Sisters house, now an abandoned museum, and Dani tags along (ugh). One of the museum’s artifacts is the Black Flame Candle, and legend has it that if a virgin lights the candle on Halloween night, Winifred, Mary, and Sarah Sanderson will come back from the dead. So what does Max do? He lights the motherfucking candle. To prove that he is a bad boy who doesn’t think about yabbos all the time, apparently.

Did he get laid? Nope.

The Deflowering (Or Lack Thereof):

Leah Pickett

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