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- Not exactly this trope, but fitting well enough: "Death Talks About Life". John Constantine is embarassed 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 loadspeaker like "Size XL! Isle 3!" or Size M Isle 3!". The punchline comes when an nervous teenager goes to buy condoms: "Cleanup! Isle 3!"
Films — Live-Action
- 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.
- 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.
- In Carry On Camping, Sid 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. Bernie 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.
- 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 drugstore, 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."
- 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 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 embarrassment 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.
- 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.
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!
- 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: What kind do you want?
Eddie: Rubber ones.
Richie: Bagsy me first go with it!
Eddie: No, no, get two.
- 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.
- 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.
- 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.
- 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.
- In the first Leisure Suit Larry game, Larry attempts to discreetly buy a "lubber" at a convenience store. The clerk talks him through a Long List of options before loudly announcing his order to the store in general. Hitherto unseen people appear from behind the shelves to shout "What a pervert!" before disappearing again.
- Parodied in It's Walky!: the characters involved make the whole thing far more complicated and embarrassing than it would otherwise be.
- 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."
- Steven Merchant explained how he was too embarrassed to buy condoms from a 17-year-old checkout girl during The Ricky Gervais Show.
- 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.