Trojan Gauntlet

So your fantasy couple is finally going to consummate their relationship! Hooray for them!

If the decision to have sex is a conscious, in-advance one, rather than a spur-of-the-moment twist near the end of an episode—and especially if it's going to be the character's first time (or first time in a while) -- the characters will often prepare. This means birth control.

The acquiring of said birth control is where this trope comes into play. For some reason, buying condoms or getting on the pill is made a torturous experience that explains why most sex on TV is hasty, unplanned and thoughtless. The pharmacist will give a character a hard time about buying his condoms, or an unrealistically insensitive clinic worker will make going on the pill the most embarrassing thing possible. Even worse is if a parent or parent figure finds out, and instead of berating the character, supports their responsibility... often with humiliating advice and anecdotes. In comedies, this will be milked for all its worth.

Note that, should you ever be so lucky in real life, buying contraceptives is almost never like that these days. You buy them off the shelf, and the register biscuit doesn't glance twice at your purchases. (Unless, of course, you're buying only condoms, six feet of garden hose, vaseline, maraschino cherries, and a rubber ducky.) However, not that long ago, it was normal for condoms to be behind the counter, so you had to ask for 'em. This was something of a rite of passage.

Of course, being able to get condoms doesn't necessarily mean they will always work.

Film

 * Summer of '42 has one of the better examples of this, justified in that the movie takes place in The Forties and the guy trying to obtain the rubbers is 15 years old.
 * The teen sex comedy Trojan War has a plot driven entirely by this trope.
 * The teen sex comedy School Spirit begins with the central character running a Trojan Gauntlet that ends with him dying in a car crash and coming back as a ghost.
 * A hilarious sequence in the film All I Wanna Do involves the characters physically grappling with a can of contraceptive foam.
 * A sequence in Amazon Women on the Moon features a youth trying to buy a package of condoms. After hitting some of the usual aspects of this trope (embarrassment because the pharmacist is a family friend, etc.), the trope is spoofed when the youth is surprised by the president of the condom company coming out of hiding and informing him that he is the condom company's one millionth customer. This "wins" him the privilege of being the condom company's public mascot for a year, at the cost of entirely spoiling his planned evening of passion.
 * When Seth Green's desperate character finally convinces a girl to sleep with him in Can't Hardly Wait, he immediately rushes upstairs to limber up, put on more deodorant, try on condoms, etc. When his (female) ex-best friend walks in on him, the bathroom door jams and they are stuck inside for almost the rest of the movie.

Jokes

 * Inverted in an old joke: a man with a tic that causes him to keep winking goes to a job interview. At one point, he reaches into his pocket for some aspirin, but a huge pile of condoms spills out. "It's Not What It Looks Like!" he says. "Have you ever tried asking a pharmacist for aspirin while winking?"
 * Inverted in a joke from the 1980s when smoking was becoming unfashionable: A man walks up to the pharmacist's counter and says "I'd like a box of condoms," then adds in a whisper, "and a pack of cigarettes."

Literature

 * The Tom Sharpe novel Porterhouse Blue features a particularly elaborate Trojan Gauntlet that culminates in the unfortunate victim dying when a chimney full of gas-filled condoms explodes. (It Makes Sense in Context.)

Live Action TV
"Mike: "Where do you keep your Durex? I need to be armed!" Dalek: "DUREX, THE BIGGEST THREAT, EXTERMINATE THEM ALL! EXTERMINATE! EXTERMINATE! EX-(hotel owner hits Dalek on the dome) OW!" Hotel owner: "Well I've got two in my wallet..." Dalek: "TWO?" Hotel Owner: "I don't work social hours, you know!""
 * The titular character on Felicity was humiliated repeatedly over the course of an entire episode over her decision to have sex with love interest Noel, including one Planned Parenthood employee's condom usage demonstration with a hilarious red plastic penis.
 * On Dawson's Creek, Dawson Leery needlessly experienced this due to the incorrect assumption that condoms are still kept behind the counter in pharmacies and asking the pharmacist to give him some.
 * Averted on Scrubs when J.D and Kim's offscreen inability to obtain a condom resulted in the pregnancy storyline that drove the sixth season.
 * In an episode of That '70s Show, Eric goes to the pharmacy to pick up some photos while his girlfriend's father is there to pick up her prescription, which he believes to be cough syrup. When the pharmacist tells him it's birth control, Eric bolts out of the store.
 * For an unfunny example, in the pilot of Mad Men, the gynecologist prescribing Peggy her birth control pills thoughtlessly humiliated her throughout her exam.
 * On Friends, Monica and Rachel once had a long, hilarious scene fighting over the last condom in the bathroom while Ross and Richard awkwardly waited together outside for the two to come to an agreement.
 * In the Degrassi Junior High episode "The Best Laid Plans", Wheels runs the Trojan Gauntlet while trying to buy condoms for a night with Stephanie. After various humiliations, he manages to buy some from a pharmacist who turns out to be Stephanie's mother, which gives the game away when he arrives at her door.
 * On The Golden Girls, the girls attempt to discreetly buy condoms, to be subjected to a loud price check everyone in the store hears.
 * Fortunately, the embarassment leads to a crowning speech of awesome.
 * Inverted in a Sex and the City where it's Miranda needing to go off birth control (due to breaking up with Steve) that causes embarrassment at her gynecologist.
 * Subverted in House, where a girl concocts a scheme involving her mother's flu (and inability to speak English) to gain access to some birth control pills. House sees through the ruse immediately, but plays along with it until he reveals the truth to the mother, and then tells the girl she could have just walked up to the counter and asked for the pills for free.
 * Incorrect. The girl comes in with her non-English-speaking mother, and tries to get the pill on prescription. House doesn't buy it, and tells her that she can buy it over the counter. Later, the girl accidentally takes the flu pills, and gives the mother the birth control. Hilarity Ensues as the girl tries to lie to the mother, and House angrily tells her that the girl is the one who mixed up the pills. The girl asks if House can speak Mandarin, and House says that he can count to ten, ask where the bathroom is, and most notably "Your daughter is pregnant."
 * Except that oral contraceptives require a prescription in the USA (some other nations don't). So you can't buy them "over the counter" in the United States (where the show takes place).
 * There's an hilarious scene in the dark comedy G.B.H. where labor leader Mike Murray, eager to make love to the beautiful blonde waiting in his hotel room, tries to find a packet of condoms in the middle of a Doctor Who convention. Unfortunately the hotel's vending machine is empty thanks to a large influx of firemen the previous night. Mike has to borrow some from the hotel's owner who's in his office with several conventioneers, including one dressed as a Dalek.

"Richie: What kind do you want? Eddie: Rubber ones."
 * Everybody Loves Raymond devotes a Halloween episode to this one. In deference to the relatively family-friendly nature of the show, the condoms are referred to as "the stuff". So Ray buys "the stuff" to prove to Debra that he can be responsible. Brightly colored ones, to be specific. Unfortunately, before Ray gets to use them, Frank sees them in the bag on the kitchen counter and, thinking they're colorful candy, gives them to the trick-or-treaters.
 * Bottom does this in the first episode.

"Richie: Bagsy me first go with it! Eddie: No, no, get two."
 * And later:


 * Seinfeld's episode "The Sponge" sees Elaine's preferred method pulled off the market leaving her desperate to find whatever sponges remain in New York. This, of course, leads to the Catch Phrase "Spongeworthy."

Music

 * The song "House of Fun" by Madness is made of this trope. The lyrics concern a sixteen year old attempting to buy his first condoms with... little success.

Urban Legends

 * This page wouldn't be complete without a mention of The Blind Date.

Web Comics

 * Parodied in It's Walky!: the characters involved make the whole thing far more complicated and embarrassing than it would otherwise be.
 * Subverted in this Red String page and the following one. Serves as something of a one-time Unusual Euphemism, as well.
 * Explored creatively in this Saturday Morning Breakfast Cereal.

Web Original

 * Steven Merchant explained how he was too embarrassed to buy condoms from a 17 year old checkout girl during The Ricky Gervais Show.

Real Life

 * There have been a few well-publicized incidents of pharmacists refusing to dispense contraceptives on religious or moral grounds, with an attendant controversy over the rights of the pharmacist versus those of the customer.
 * Back in The Fifties, this was Truth in Television. Condoms were sold as a behind the counter item; you had to actually go up to the pharmacy counter and ask for them. (Not like today, where you just grab the kind you want off the shelf and go pay for them.) (And heaven help a woman who attempted to buy them, even if she was married.)
 * Still Truth in Television at times; condoms tend to grow legs—due to a combination of, among other things, being costly for their size, the embarrassment factor, and their resale value—and some places keep them behind the counter for that reason.
 * Go back even further and it was illegal for the pharmacist to sell them to unmarried people. So you would have to prove you were married.
 * Tech Marches On and more or less renders this trope irrelevant: nowadays, every large pharmacist has an online store.
 * Of course, if you're in a hurry, you might not want to order online and wait for delivery.
 * And if you're in that much of a hurry, that just opens up a whole other can of worms.