This trope is the reverse of the virgin as portrayed in classical literature. In ancient myths, virgins were often dedicated to some higher purpose. They were supposed to be above such things as lust and passion, upheld as an example that people should strive to follow... and if they fell from this pedestal, boy, did they fall hard. Just ask the goddess Artemis' attendants; if they gave in to the pleasures of the flesh, there was a world of hurt in store when the Boss Lady found out.
But sometime in the 20th century, there has been a sharp reversal. Virginity no longer guarantees Virgin Power or some higher knowledge; in fact, it often indicates the opposite. Many contemporary characters who are still virgins over the age of consent will be The Ditz. The men will be shy to the point of social ineptitude — or so desperate to prove their manhood that they make idiots of themselves. By contrast, female virgins are usually portrayed as hopelessly dim, both in terms of intelligence and social skills. At best, such characters may be good at their jobs and/or book smart, but naive to the point of ignorance (remember, this trope often overlaps with The Ingenue).
On the upside, these characters will seldom be downright nasty. While some virgins are inept-but-harmless, most are examples of Dumb Is Good. They're usually sweet-natured and kind - you just wouldn't want them on your quiz team. In fact, their pleasant demeanor is one of the qualities that makes the opposite sex (and sometimes the same sex) want to sleep with them, whether it's because they appreciate these nice qualities... or because they can't resist the challenge of deflowering an "innocent".
It's this plot line that showcases Virginity Makes You Stupid at its worst. A conniving Vamp or Casanova sets themselves the challenge of sleeping with someone previously thought as pure, untouchable, naive. And their target will almost always fall for it, even when anyone with two functioning braincells could spot their intentions from a mile away.
The Family-Unfriendly Aesop in this case seems to be that in order to understand how people work, you have to have slept with someone. Clearly, basic common sense, body language, and the word "no" are a poor defense against manipulative bastards with a sex drive. To be fair, generally the (former) virgin's goodness will transform their pursuer into a Jerk with a Heart of Gold... but probably not before they've slept together. In total, Sex Is Good, no questions asked.
Rather than being shamed or punished for losing their virginity, a character is promoted. Their sexual initiation will magically solve all of their personality "problems" and they will usually become more capable, rounded characters.
There are many possible explanations for this trope. It may be part of a larger trend where anyform of innocence or optimism is interpreted as foolish. Perhaps it's inconceivable to a sex-orientated media that anyone with half a brain would choose not to have sex. Or maybe a lack of carnal knowledge was taken to mean a lack of knowledge of carnal matters and then extended to any general knowledge as well.
See also: My Girl Is Not a Slut, A Man Is Not a Virgin. In the context of musical theatre, this character will ALWAYS be The Soprano or a Tenor Boy (frequently called a "dolt-boy"). Compare Innocent Bigot and Innocently Insensitive; contrast Virgin Power. Exceptions to the "nice-but-dim" virgin rule occur when there is a Chaste Hero or Amazon Brigade running the show - even then, expect their virginity to be challenged (and more likely than not, relinquished) at some point in the plot.
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In the anime version of Valkyria Chronicles, this was reasonably inferred from the game about the protagonist Welkin Gunther, but the anime goes on to show that if Welkin has a fault aside from being a little too much of a Nice Guy, it's this trope. In college, he had a chance to get married to the most sought after girl in school, and he friend zoned her almost immediately, and his best friend (who also hit on the same woman) blatantly lampshades it. By present day, it's obvious Alicia Melchiott has feelings for him, but Welkin repeats history to the point Faldio not only starts hitting Alicia himself, but in his frustration over Welkin's use of this trope he throws down the gauntlet in Episode 12 and tells Welkin he has feelings for Alicia himself as a Batman Gambit to get Welkin to grow a spine and sex drive and see Alicia as a woman. Thankfully, by the end of the game and anime, he wises up.
Belldandy, oh Belldandy. She can live fighting demons and impeding doom and usually be the most competent character in the series, but was completely sheltered from damaging knowledge such as the fact that guys have penises and that lovers usually kiss. Her most blatant example of this may have been when Aoshima tricked her into coming with him into a love hotel. She recognized the decor — because Urd had earlier done up Keiichi's room in the same style — but still didn't seem to have any idea of Aoshima's intentions until he grabbed her and shoved her down on the bed. At time she has shown more initiative in terms of her relationship with Keiichi and has even kissed him while he's been asleep, but she also seems to be both ignorant and terrified of sexuality.
Not to mention naive, like when they were at the hot springs and she thought Marller injured him because he was covering himself up, totally unaware that he was embarrassed at being nude. Or when the two of them were at a love motel during an Urd-created rainstorm and while Keiichi was wondering if she was ready for sex, Belldandy was completely unaware of where they were, she was only focused on the rain.
Inverted in Hellsing with Sir Integra, holder of "100% virgin blood", yet portrayed as intelligent, highly competent, downright badass and ruthless.
Come to think of it being a virgin in Hellsing is pretty awesome, you can still become a vampire, and on top of that, it is reasonable to assume that at least a few of the major badass characters (like Alexander Anderson) are virgins.
Inverted a little too far by Ghost in the Shell: Stand Alone Complex 2nd Gig. The amoral ChessmasterBig BadGohda reveals he's actually a virgin. He used virginity as the final necessary trigger for activating the Individual Eleven virus in a subject, since the trigger for the virus was having been a virgin before switching to cybernetic body, and besides a cyber brain Gohda is still a flesh and blood human.
He thinks a condom is used to hold a backup water supply!
One assumes that he knows what the intended use is, but the reason he carries one is for utility: an actual recommended use for condoms in militaries and survival guides is as emergency canteens, being light weight, durable and able to store a liter of water with ease. He just doesn't care about the more conventional use.
After sleeping with Mao, Kurz goes to Sousuke to talk about the subject. It takes a very long time (and an outburst heard by everyone on deck) for Sousuke to figure out what he means by "sleeping with".
To defend Goku, he lived most of his life with his adoptive parent in the wilderness, who happened to also be a martial artist. His first social meeting with someone other than this adoptive parent happened at the start of the series when he was a teenager and most of what he had been taught was how to talk, how to fight, and how to eat. I.E. he had no real reason to know what marriage was in the first place.
His son Gohan also seems to have inherited his father's cluelessness, as Videl had to jump through hoops to get him to notice her love for him.
Pandora Hearts offers a hysterical subversion of the standard plot with Ada and Vincent. The Manipulative Bastard and The Casanova's thoughts directly reveal he finds her innocence sickening and only wants to see her tainted. When he asks her to 'lay herself bare' and 'show him the real her', she nervously agrees and leads him to an unused home of her family's only to reveal she didn't pick up on the sexual implications at all; rather, what she shows him is the "real her": an obsession with magic, darkness, and torture. Needless to say, poor Vincent is too shocked (and annoyed) to bother going through with his plans for the time.
At least once in Code Geass, C.C. calls Lelouch a "stupid virgin" (which was changed in the English dub). Lelouch is actually very intelligent under most circumstances, but in that situation C.C. was criticizing him for letting his feelings for a girl jeopardize his overall plans.
While Keith Goodman's ditziness and chasteness have occasionally been demonstrated, the fourth Tiger & Bunny Drama CD just how phenomenally dense he is when it comes to sex: he invites Ivan to a rather risque gay club. That he goes to regularly. Completely oblivious to the fact that it's a gay club.
Ivan: [As Fire Emblem said, this was a club that catered 100% to his taste. It was sort of like a Host Club. As to why Sky High called me out to it...]
Keith: Why, you ask? It's because this place has the most delicious lemonade in the city!
Nathan: It appears our dear Sky High thinks this is a cafe.
Subverted in Anatolia Story. While Yuri is notably more reserved and shy about sexual matters than the other women of the time period, she is just as much a Guile Hero before sleeping with Kail for the first time as after.
In Astérix and Son, The Fool Obelix, while much more prone to flirting and blushing around lovely girls than Asterix is shown to be, unintentionally reveals that he has no idea how babies are made, still believing in the Delivery Stork despite being in his thirties (maybe?). Asterix, who is much less excited by girls (but implicitly because he's quite experienced), is aghast that he managed to get to his age without ever finding out and promises to explain the details to him later. In the final panel, we catch the tail-end of this explanation, and Obelix earnestly asks what the stork is for, in that case. This was after the second writer took over writing, so it's possible it was just his Man Child qualities receiving some Flanderization.
The plot of Legend is kicked off when Jack takes virginal but headstrong and foolish Lili to see unicorns, which she just has to touch despite Jack's protest to the contrary. That contact sullied the unicorn enough to let the minions of Darkness take its horn.
She does show enough smarts later to trick the devil and save the unicorn from him, though it's arguable whether or not the fact that he tries (and nearly succeeds) in seducing her counts...
At least, Cecile demonstrates this trope perfectly. Annette is actually fairly intelligent, and sees straight through most of Sebastian's attempts to get her into bed. She falls for him only once he has truly fallen for her, and she can tell when he's genuine and when he's faking.
Forbidden Planet explicitly relates to Altaira and a docile tiger to the legendary virgin and unicorn. Sure enough, the tiger turns on Altaira after she loses her virginity, but this turns out to be justified: the apparently misplaced Terran animals on Altair-4 are completely unnatural creatures.
She doesn't lose her virginity, just her innocence. But that seems to be enough.
The virgin of the 'heroines' in Hostel II is flaky, socially awkward due to anxieties, emotionally immature and lacking common sense. It doesn't even take a Casanova; a little alcohol and desperation for acceptance lubricates her path to Death by Sex.
The 40-Year-Old Virgin plays with this trope; Andy is definitely a bit of a naive Manchild, and the plot of the story revolves around his quest to get rid of his virginity, but the story gradually makes clear that he's actually a lot more well-adjusted, mature and sensible than many of the more 'experienced' men and women around him.
Liv Dean from Duets is portrayed as being very gullible which, combined with her beauty, makes her a popular target for men. For the most part, though, she avoids trouble by being completely oblivious to it, much to her estranged father's chagrin.
Liv: "I stayed in a room like this with Tom Jones for about a month!"
Ricky: "Oh, I bet I know what you were doing with Tom Jones for a month..."
Liv: "What... No! It wasn't like that! He said he just wanted someone to keep him company!"
In the 1987 movie version of Dragnet, to some extent Joe Friday and Connie Swail, although it's more them being incredibly old-fashioned and uptight than idiotic.
Don't you mean the virgin Connie Swail?
Averted in Clueless, when the super-cool Cher reveals that she never......
Invoked in The Last Temptationof Christ when Jesus throws the money-changers out of the temple. One of the patrons recognizes him as Jesus from Nazareth, and notes the lack of sex has forced the semen to back up into his brain.
In many variations of the "Virgin and the Unicorn" tale, the maiden was duped into attracting and soothing her unicorn friend until the hunters who convinced her to do so could attack and kill the unicorn for its horn. The version found in Nigel Suckling's The Book Of The Unicorn goes so far as to have the virgin princess ask her father — a tyrannical, greedy king — why they have brought a large company of armed men to meet a peaceful creature such as a unicorn. Amazingly, she believes him when he reassures her that they are there only for her protection. What an Idiot indeed.
Modern unicorn stories challenge this trope, although they do it in different ways. The novel of The Last Unicorn includes a scene where a maiden tries rather half-heartedly to summon a unicorn as part of a ritual she has to perform before she can get married. The scene serves to show that virgins can be every bit as cynical and self-serving as anybody else. (It's also heavily ironic, since the only unicorn in the world is there to see it and decides not to go to her.)
Von Jocks' short story Yes Virginia, there is a Unicorn redefines the terms of the word "virgin" altogether. The youngest of the story's three female protagonists (and the only "technical" virgin), however, falls squarely into this trope and has to be protected from conniving men by the unicorn.
The short story White Beauty by Cynthia Ward features the virgin-as-bait-for-unicorn trope, but throws the hunters for a loop when, despite its looks, the unicorn turns out to be a vampiric creature that drains the girl's blood with its horn. Didn't See That Coming, indeed.
Subverted in one of Alan Dean Foster's Spellsinger books - it doesn't work, because the unicorn in question is both gay and apparently not too enchanted with humans.
Also, the human girl they attempted to use to summon the unicorn was a streetwise orphan who was definitely not stupid.
Terry Jones of the Pythons related, in a book on medieval folklore, his surprise in finding that the pure virgin/unicorn thing was a sort of Forgotten Trope /punchline. The joke being you send a mythical creature to FIND a mythical creature. The joke has been repeatedly reinvented since; see, for instance, the conversation between the monster-hunters in Guards! Guards!!
Subverted with the manga-esque series Tales of the Dark Forest. Virgins have to be smart, so they can outwit and kill the unicorns they stay virgins in order to hunt. The reason it's a subversion is that the first virgin we see in the series is used for unicorn bait, and really is that naively stupid at least until she's on the run with and apprenticed to a real unicorn huntress. Then again, she did arrange for said huntress' deflowering beforehand.
T.H. White's The Once and Future King has Gawaine and his brothers, while children, pull a servant girl from the kitchen to use as bait to catch a unicorn. It works, but Agravaine ends up killing the unicorn because of his... issues with his mother.
There's an interesting inverse example there as well. The boys get the idea to go unicorn-hunting because their mother went off on one with some knights, acting as the virgin. Clearly she isn't one, since she, you know, has sons. Even though their mother is a dark sorceress who has no problem manipulating people to have her way, she's still something of a shallow flake who can't stay focused on any serious matters for long.
In one of the books of The Witcher, Spoony Bard Jaskier is mocking a moment of Wangst of the protagonist, monster hunter Geralt. He compares witchers, who hunt monsters with the Virgin Unicorn Hunters, who eventually gave up on their virginity when Unicorns went extinct and took up other professions and everyone was happy.
Sherlock Holmes, while almost certainly a virgin due to his disdain of romantic love, was no fool. His less-gifted friend Watson was married(presumably with all that entails), but it's not quite an aversion, as Watson was much more capable than many adaptions painted him to be, especially given anyone will look less-gifted next to Sherlock Holmes.
Brienne of Tarth, too, though we meet her only after she's already become a tad disillusioned in regards to men. She's still a complete Wide-Eyed Idealist, but once she believed that all men were as noble and true as her father, whom she looks to as a paragon of virtue. After being spurned all her life due to her appearance, imagine her confusion and hope when men in Renly's army finally started flirting with her. Then imagine her heartbreak when she was informed that they were doing so as part of a bet to see who could get to her maidenhead first.
Lady Crysania, Head Cleric of Paladine in the Dragonlance books, fits this trope. Though very sophisticated and intelligent, she is also very ignorant of "the real world". Part of this is due to her sheltered upbringing rather than just lack of sexual experience. She does manage to fall in love with Raistlin over the course of the Legends trilogy, resulting in a two-virgins-passing-in-the-night scenario where Raistlin at one point inhabits the healthy, curse-free, and virile body of Fistandandilus. He struggles with urges he's never dealt with before and considers seducing Crysania (who'd likely be more than willing if only he'd make the first move) but backs down, remarking that he knows next to nothing about seduction or lovemaking. Oddly for Raistlin, the possibility that Crysania's implied Virgin Power might be necessary to open the Gate comes in a distant second for reasons not to make a move.
Inverted as regards Raistlin and his twin brother, Caramon. Caramon is strong, handsome, and (prior to settling down with Tika) has a tendency to sleep with any available, willing, and pretty girl, but is also naive and not terribly bright (prior to Character Development in the Legends trilogy). Raistlin is a socially withdrawn virgin who generally considers sex beneath him (okay, he may have had sex once- and then had his memory of the event wiped; the canonicity of that story is deliberately ambiguous), but he's also deeply cynical and frighteningly intelligent.
In Tanya Huff's Summon the Keeper, Dean is a knock-down gorgeous guy, kind, handy around the house, and so well-grounded that world-weary Claire instinctively looks for roots sprouting from his sneakers. He's twenty and yep, a virgin. He blushes at the slightest hint of any "funny stuff", takes a while to understand anything, and Claire falls deep and hard for him. In subsequent books, Claire and Dean do end up together, love-smitten enough to make you barf, and he loses his virginity quickly in the second book.
In the Discworld novels, the witches Nanny Ogg, Magrat and Granny Weatherwax fit The Hecate Sisters mold. As the maiden, Magrat is nominally the virginal one and is The Ditz. This gets contrasted with Nanny Ogg whose "maiden" years involved her really getting around, linked it seems with her becoming the most knowledgeable midwife of all time (in fact Time gets her to be her midwife). When a (rabid, feral) unicorn needs catching, the only one who can do it is Granny Weatherwax, proving that you can be a virgin and a proud, cynical badass. As Nanny Ogg says to Archchancellor Ridcully: "She always could run faster'n you..."
Dracula: Jonathan Harker. It doesn't help that every time he does get a chance to hop in bed with his wife, a certain somebody tends to interrupt. With blood-drinking.
Lucy Westenra even moreso. The only character who is explicitly not a virgin, in fact, is Abraham Van Helsing, the Omnidisciplinary ScientistMentorSmart Guy. Subverted by the fact that, after Van Helsing, the second-most-competent person around seems to be Mina Harker, who is almost certainly a virgin (although Dracula does symbolically rape her at one point...)
Warden Ramirez of the The Dresden Files, despite all his big talk, is a virgin. He's not exactly naive though, and he's confident and competent enough to be a Warden. Lara Raith is so stunned that she mockingly asks if Dresden brought him as a present for her. He even manages to come out of a White Court house with it intact. Mostly because of the sword and grenades and other killy things.
Cecile Volanges in Dangerous Liaisons even after forsaking the basic requirement for this trope. She didn't even realize she was pregnant with Valmont's child until she was in the middle of her Convenient Miscarriage and he explained what was going on. To be fair in the 18th Century (noble) girls were kept pretty ignorant on this topic.
In Mercedes Lackey's By the Sword, the heroine's mother had just enough instinct to avoid falling for a cruel noble with an eye to her estate but otherwise exemplified this trope, thanks to a head stuffed full of romance stories and bad poems.
Besides the aforementioned examples in The Once and Future King, Arthur himself is a very naive and sweet person when he's still a virgin. He loses his virginity when he's seduced by his half-sister and the narrator even says that "innocence is not enough". Things quickly start to go downhill for him from there. Lancelot likewise finds his life going much more complicated and thus making him much less idealistic and innocent after Princess Elaine rapes him and takes his virginity. He is very upset, mainly because he believes that only virgins have the power to work miracles.
This must be a thing in the Arthurian mythos. The prologue to The Mists of Avalon implies this. As Morgaine considers the Blessed Virgin Mary as a possible aspect of the Goddess, she dismisses the idea with "What does a virgin know of the sufferings of mankind?"
Was John Galt of Atlas Shrugged a virgin? Certainly he would never have sex just to "do it" until he had met his perfect woman. Dagny Taggart appears to have only two lovers - one who really loved her and another who seemed to view sex as a sign of his major character weakness. Whether Galt was a fool or not kind of depends on your view of economics and politics.
Live Action TV
Quite a lot of Hispanic Soap Operas do this regularly, because of all the drama you can milk from the habitual consequences of sex in countries which are mostly Catholic, and I'm not talking about pregnancy. Strangely, this applies even if the Official Couple marries (but only if they do that in the middle of the story).
Played with to great effect in "Yo Soy Betty La Fea": given her awful appearance, her social awkwardness, her nerdiness and her heroine status, you couldn't suspect she wasn't a virgin anymore... until she confesses to her romantic interest after their first night together that her first time was with a boyfriend who did her only because of a bet, and the experience left her so hurt she preferred not to talk about it. Too bad she didn't learn the lesson then.
In its America adaptation Ugly Betty, Betty outright told Christina in Season 1 that her boyfriend at the start of the series (Walter) was the only guy she'd ever "...you know." Christina is kinda grossed out by the idea of Walter-on-Betty sex.
Juliette, the main character in SeptièmeCielBelgique is a very shy and inexperienced woman, both sexually and romantically speaking, who suddenly ends up in a job environment with a boss who is a Ms. Fanservice with a penchant to let slip about her sexual life, and an old flame she believes is a heartless The Casanova. She compensates with a lot of shameless lies about her romantic past (easily uncovered by just seeing how uncomfortable she becomes when sexual themes arises), a cynical attitude who quickly descends into Tsundere territory, and a tendency to take a lot of her prejudices and misunderstanding for real. Although that attitude makes her immaturity more obvious, she somehow manages to hide her virgin status to the other characters until the end of the first season, just before losing it. Interestingly, in the second season, her lack of knowledge about how relationships works and her Tsundere attitude remains even after she had sex and began a (strained) relationship with her romantic interest.
Averted in Babylon 5 by Marcus Cole: He's idealistic and good-natured, but he's also worldly, deep, and completely badass. And he's saving himself for Ivanova; as with any relationship involving Ivanova, she finds out too late.
In the Doctor Who episodes "The Impossible Planet" and "The Satan Pit", the character who is identified as a virgin is a sniveling do-nothing who sits fetal in a corner while the other characters work to survive, winding up possessed by Satan and eventually blown out a window into a Black Hole.
Though the BBC series Sherlock generally averts this very adamantly (with the titular hero being both a virgin and one of the three most intelligent characters in the show), the one episode in which Sherlock makes the largest number of mistakes, practically commits treason, and is completely taken in by sometimes-Femme Fatale-on-and-off-Vamp Irene Adler, is also the episode in which he develops a tremendous crush on her — a crush that he seems to have no idea what to do about, despite Irene repeatedly offering to...ease the tension, as it were.
Paul Rudnick's I Hate Hamlet includes a 29-year-old virgin, who while not an idiot, is incredibly childish and idealistic. Her boyfriend calls her "the victim of a relentlessly happy childhood, which she fully expects to continue." Eventually, a lascivious ghost helps her realize her desires, and she and her boyfriend, well...
And at the start of 7, after having sex with Larry she's lost all her purity and goodness, and abandons him to find a "real man". While he's tied up. In a room she (accidentally) set on fire. Does having sex with Larry make you evil, or does he simply have a very bad track record?
In Mass Effect, Liara has little social skills due to spending decades on solitary studies. Guess what? She is also a virgin. Ash, not so much. Also, Liara is the species equivalent of around 20-something human years old... which is 106. However, she is an archeologist specializing the Protheans, and she did piece together from her research that something happened to the Protheans and organic life before them consistently (which is the Reapers, the main threat within the storyline), so she's clearly not stupid. She states her social inability is from her constant researching in the field and out of it leaving her alone for lengthy amounts of time.
Princess Cassidy in The Royal Trap, due to having been kept so excessively sheltered by her parents that she hadn't even seen naked statuary. When the main character commented that there was a difference between men's and women's bodies she replied "Of course. That's why women wear gowns."
Matt of Concession almost seems to gain 20 IQ points after hooking up with Joel. Most likely related to how badly closeted he was before then.
Doubly subverted in Flipside. Regina's character is introduced as this, having been raised in a monastery and being utterly shy about anything having to do with relationships. Her lack of self-confidence is the major obstacle to her gaining her next rank as a sorcerer. Subverted when, in the "Silhouette" chapter, she suddenly reappears and starts vamping on the not-so-innocent Maytag, having apparently lost her innocence in record time. Then subverted again when it turns out not to be Regina after all.
This is seemingly played fairly straight in Ménage à 3, to begin with; The comic's main protagonist, Gary, starts the story as a naive, geeky virgin who faints every time he sees real naked breasts, and who can be fooled into mistaking a vagina for a mouth while blindfold (it sort of makes sense in context), although he's not entirely stupid in other respects. However, trope-avertingly, when he eventually loses his virginity, he doesn't change; his problem, it seems, is not being a virgin it's being a geek, and specifically being Gary.
Played straight and subverted at the same time with Norman Gates from Poisoned Minds, as told in this strip. He's a dumb brute, but certianly not innocent. He just seems to genuinely lack those particular cravings, being busy spreading chaos and destruction instead.
Subverted in Shortpacked!, where the shy and (comparatively) sweet one has "never been the virgin", while the most sex-crazed of the lot never quite managed to get all the way.
In Undergrads, Cal is an amiable dolt who at one point is horrified by the fact that he's gone hours without sex, while virtually all of the other characters are both more intelligent and far less sexually experienced.
"It turned out that the princess didn't know a damn thing about sex — how does she get guys to pay her rent?"
One French verb for "to lose one's virginity", se déniaiser, basically means "to de-idiot oneself".
Given that the standard Biblical euphemism is "To know," the link between obtaining knowledge and... well, de-idioting isn't too hard to follow.
Okay, a little etymology here: a "niais" originaly literally meant "a hawk which has yet to leave its nest for the first time", by extension it started to mean "someone without worldly experience", at which point se déniaiser merely meant "losing one's inexperience": the niais = idiot meaning came later.