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 the 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 if for no other reason than the advent of HIV & AIDS created a very strong imperative to make barrier sexual protection as widely and easily available as possible. You buy them off the shelf, and the person at the counter won't even 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.) And with self-checkout machines becoming widespread in the 2010s, it's even possible to buy them without interacting with another person. Between this and changing views on sexuality, this trope has largely become a Discredited Trope. 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 and sometimes is still considered this to a slight degree even today - the idea being that if you aren't mature enough to go and buy condoms by yourself, you aren't mature enough to be having sex either. In order to facilitate this trope (or at least its potential for hilarity ensuing) within these changing social mores, the trope may therefore be combined with A Simple Plan, in that what seems like the simple act of acquiring contraception will, through a collision of unrelated circumstances, become far more tortuous and complicated than it should be.
Nevertheless, many still see it as being a bit embarrassing—or at least a bit gauche—to buy condoms and nothing but condoms. For one, given that even in these more sexually permissive days sex is nevertheless still seen as a rather private and intimate affair, the more modest and shy among us might be at least a little uncomfortable knowing that at least one complete stranger is going to know that sex is likely to be in their immediate future. So often the purchase will be mixed in with a number of other items, e.g. toothpaste or soap. For comic effect, should the other items themselves be unfortunately or hastily chosen this may often lead to a serious case of Bread, Eggs, Milk, Squick, which in turn will also provide the possibility for ensuing hilarity and comic misunderstandings.
Of course, being able to get condoms doesn't necessarily mean they will always work.
- A Levi's commercial directed by Michel Gondry is based on the "Blind Date" urban legend, which can be summarized as "Young man discovers the pharmacist who sold him condoms is his blind date's father.".
- Several UK Public Service Announcements in the eighties and nineties tried to prevent this, as part of a general move towards safe sex awareness. One had subtitles showing what the customer and the cashier were thinking, with the message being something like "She already knows so at this point, it's probably less embarrassing to just buy them."
- The Sandman, Not exactly this trope, but fitting well enough: "Death Talks About Life". John Constantine is embarrassed to the max when Death wants him to demonstrate proper condom use on a banana...
- Red Ears: There's a gag where various men buy condoms from a female cashier. They don't know their own size, so she has to, ehm, manually check them by putting her hand down their pants, then broadcasting stuff on the loudspeaker like "Size XL! Aisle 3!" or "Size M! Aisle 3!". The punchline comes when a nervous teenager goes to buy condoms: "Cleanup! Aisle 3!"
- The French social anti-AIDS ad compilation 3,000 Scenarios to Combat a Virus included a short where a DecemberDecember Romance couple needs condoms, so the man goes to the pharmacy and places the condoms in a large order of all kind of things a man his age would buy. Once out, he gleefully pulls the condoms out and they walk away, the rest of the order left in a rubbish bin. A variation of the "Blind Date" joke/urban legend is also part of the compilation.
- 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.
- In Carry On Camping, Bernie is too shy to ask for sexual magazines over the counter in the newsagents, especially when there's an attractive woman serving for the day, so he asks for toothpaste out of embarrassment. Sid realizes, "That's why your cupboard's full of toothpaste."
- Freerunner, despite being set in modern times, invoked this for a joke about the scanner not working which turned out to be a Chekhov's Skill for the goal scanners.
- The Hairy Bird has a hilarious scene where a young couple struggles with opening a can of contraceptive foam.
- In If Looks Could Kill the protagonist Michael Corben is mistaken for a James Bond-type spy, and a Femme Fatale Spy turns up to seduce and then kill him. Eager to make love to this beautiful woman, Corben searches through the effects of the spy whose place he's taken and finds a metal tube labelled COMBAT CONDOMS. As he's in the bathroom struggling to get the tube open, another assassin turns up, and blows up the first assassin with a rocket launcher.
- 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.
- Summer of '42 has one of the better examples of this, justified in that the movie takes place in The '40s 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.
- Inverted in an old joke: A man went into a job interview and his eye winked through the whole process. The interviewer said, "Look, you are well qualified, but I'm afraid that facial tic will throw off clients." The man replied - "Funny you mention that, because all I have to do is take aspirin and the winking goes away - watch" and the man began dumping out his pockets looking for aspirin. In most of his pockets, however, were condoms. Finally, once a pile of condom packages of every sort piled up on the desk the man found two aspirin, took them, and the wink totally stopped. "Well, that worked," the interviewer admitted, "but why do you have all the condoms? We don't want our clients to think you're a womanizer!" "It's quite simple, sir," the guy said, "have you ever walked into a drug store, winking like crazy, and asked for aspirin?"
- A man walks up to the pharmacist and whispers that he needs condoms.
- The pharmacist asks him what size, and when he doesn't know, gives him a board with increasingly larger holes in it, and tells him to follow in the back. The pharmacist then tells his assistant "Get me a box of extra small- no, small- no, medium cond- a box of paper towels!"
- A variation where the guy goes into the fitting room alone. Five minutes later, the guy comes back and asks "Forget the condoms. How much for the board?"
- Have several friends buy increasingly larger sizes of condoms, with the last one buying plastic bags and heavy-duty rubber bands...
- A young man walks up to the pharmacist and asks for a pack of condoms normally. He then tells the pharmacist that he'll be visiting his girlfriend at her house later that night for dinner, and how he's planning to have sex with her for the first time, but he's not sure how she'll behave in bed - she might as well be a slut for all he knows. He gets the pack, pays, and leaves without hassle. Later, at the girlfriend's house, he stays quiet and composed the whole dinner, only opening his mouth to pray before the meal. Once the dinner is over, the girlfriend comes up to him and says: "Gee, honey, I didn't know you were so shy and pious..." "Yeah," he whispers nervously, "and I didn't know your dad was a pharmacist."
- In Atypical, Zahid takes Sam to the drugstore to help him buy condoms for his first sex act. Sam picks up a box of condoms, and asks the pharmacist if he can try them on and return them, gives a fact that the first condoms were made of leather, and asks if "ribbed for her pleasure" is a guaranteed statement. The clerk responds by asking them to just take the condoms.
- Bottom does this in the first episode.
Richie: What kind do you want?
Eddie: Rubber ones.
Richie: Bagsy me first go with it!
Eddie: No, no, get two.
- A small example in Chuck. Chuck convinces Sarah to run away so that they can find his father. They stop at a motel and get a room with one bed. After sleeping in the same bed, they wake up and jump at one another. Just as it seems that their UST will be finally resolved... Chuck decides to play it safe and runs to the bathroom to put on the condom he keeps in his wallet. Only to find an IOU note from Morgan who has taken it. He runs outside to find a condom vending machine and gets caught by Casey, who was following them.
- Clueless: After a full series of him begging for it, Murray and Dionne are going to have Their First Time in the series finale. He goes to get condoms, and who should wind up behind him in line than the reverend from his family's church.
- 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.
- 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.
- One famous episode of EastEnders followed Alfie Moon's attempts to procure some condoms so he could have a passionate night in with his then-girlfriend Kat Slater. By the time he managed to get back with some, Kat had fallen asleep.
- 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.
- The title 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 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.
- Full Frontal. A parody of a Public Service Announcement about safe sex had a couple agreeing to do the deed, but the man doesn't have contraception. He then lists exactly how many condoms he'd have to buy just on the odd chance he'd have sex that night until the woman becomes annoyed and storms off to buy some. He then turns to the audience and says that you can always get women to buy your condoms.
- G.B.H.. 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.
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...
Hotel Owner: I don't work social hours, you know!
- 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 embarrassment leads to a crowning speech of awesome.
- In an episode of Head of the Class, as nerdy Arvid prepared for his date with the school bike, he ventured to the drugstore to purchase condoms. Of course, he was thoroughly embarrassed and thwarted at every turn. He finally prepared to leave the store when a completely random woman—who'd apparently figured out the reason for his nervousness—called him out, telling him "don't you DARE leave here without those condoms!" and proceeded to buy them for him, lecturing him on safe sex and responsibility.
- iZombie: When Ravi is testing whether the zombie virus is sexually transmittable, he says the store clerk will look at you real weird when you buy every brand of condom they have.
- Jack & Bobby has one where Jack and his best friend are staring at the condom selection at the supermarket, trying to figure out what size to buy. Then his mom Grace winds up behind him in the checkout line. Of course, she compliments him on being responsible and tells the cashier to charge her for the condoms, which only compounds Jack's embarrassment.
- For an unfunny example, in the pilot of Mad Men, the gynecologist prescribing Peggy her birth control pills thoughtlessly humiliated her throughout her exam.
- One of Mark Lamarr's intros on Never Mind the Buzzcocks (which all had the format "The pop quiz that likes to say '[line from song], [line that changes the meaning]") was something like "The pop quiz that likes to say 'And through it all, she offers me protection, but I always leave the chemists with a pack of indigestion tablets".
- 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.
- 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 catchphrase "Spongeworthy." This gets a callback in the final episode when the pharmacist is called to testify against her and her need for birth control is made to make her sound like a loose woman rather than one taking responsibility for her reproductive health.
- 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.
- 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.
- In a similar and kind of Inverted example: in one episode, Kitty provides Eric with a bag of condoms, which is embarrassing. However, later Kitty and Red are planning to have sex and realize that they're out, so Red sneaks into Eric's room to take one. Eric walks in, Red is angry/embarrassed, and Eric freaks out because he incorrectly believes that Red saw his marijuana stash.
- Episode 8, Season 2 of Unbreakable Kimmy Schmidt Kimmy has to buy condoms in a convenience store.
- Played with in Wet Hot American Summer, First Day at Camp. Victor wants a box of condoms, and goes to a nearby store. He buys, a comb, a copy of TV Guide, a key chain, a deck of cards, the condoms, and some lube. The clerk then calls for a price check, setting up the expected joke of the conspicuous price check on the condoms and lube. Instead, the clerk asks for a price check on the key chain. Victor panics and tries desperately to stop the price check.
- 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. Though this is in large part because he Cannot Spit It Out and instead comes out with increasingly bizarre and ridiculous euphemisms for condoms that just confuses the chemist into thinking he wants to buy some balloons.
- In Leisure Suit Larry 1: In the Land of the Lounge Lizards, Larry attempts to discreetly buy a "lubber" at a convenience store. The clerk talks him through a Long List of options before loudly "repeating" his order (intentionally getting it wrong, including giving the size as "extra small" regardless of what you said) to the entire store. Hitherto unseen people appear from behind the shelves to shout "What a pervert!" before disappearing again.
- CollegeHumor: They parody this in the POV series where buying condoms is shown from both the guy's perspective and his girlfriend's. The guy finds it embarrassing and tries to hide it by buying half a dozen unrelated items. The girl doesn't know the guy's size so she just buys all of them.
- They also did another variation for their "Dating: It's Complicated" series. A young college-aged couple are at a party, and they get drunk and fall asleep or pass out in one of the bedrooms. They wake up at about 3 AM, and begin making out...and the girl says she wants to have sex. Her boyfriend is excited because he's a virgin (well, technically)...but he unfortunately doesn't have any condoms with him. The girlfriend replies that she has a condom in her purse...which is locked in one of the other bedrooms. She sends him down the hall to get it, and he is unable to get into the room, ask for help, or pick the lock. He proposes a number of makeshift condom ideas (balloons, beer bottle, plastic wrap), but his girlfriend shoots them all down. Then she asks him to go ask the apartment's owner for a condom, but he refuses because it's too awkward. So they decide to go with their old standby: the Everything But. When they finish and turn on the lights, there's a brand-new box of condoms right on the bedside table...and the owner of the bed/apartment angrily kicking them out. When they finally do get the opportunity to go "all the way," the girl is on her period and in a bad mood.
- Steven Merchant explained how he was too embarrassed to buy condoms from a 17-year-old checkout girl during The Ricky Gervais Show.
- Snopes has "The Blind Date" urban legend, which can be summarized as "Young man discovers the pharmacist who sold him condoms is his blind date's father."
- Inverted in Mission Hill, at least in term of the ages involved. Teenage Kevin is working as a cashier when his gay, adult neighbor Wally comes in. He seems nervous that Kevin's the one working there, makes awkward chitchat, and then goes outside to have a frantic discussion with his boyfriend, Gus. Gus then comes in, clearly annoyed, and asks Kevin for some condoms.
- Inverted in an episode of The Simpsons, when Homer openly buys a packet of condoms (and similarly embarrassing items like a disposable enema and pantyliners) while trying to cover up the fact that what he really wants to buy are fireworks (which are illegal in the state the family is currently vacationing in).
Marge: I don't know what you've got planned later, but count me out.