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Homestar: Mainly, I just want to keep [Marzipan and The Cheat] from making out.
Strong Bad: Euw! The disgust! It won't wash off!
Homestar Runner, "Date Nite"

A mostly comedy trope. Two people are in the process of getting together and having a date. The more they try to keep it on the down-low, the more likely it is that everybody they know is spying on 'em.

The peepers usually overlap with Shipper on Deck, sometimes even trying to speed things up with the "lucky" couple. Other times they have the specific goal of ruining the thing, which may result in a Bad Date.

Truth in Television, although perhaps not as common as fiction would have you believe.


Examples

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    Anime and Manga 
  • The 100 Girlfriends Who Really, Really, Really, Really, Really Love You: In Chapter 105, Shizuka and Kusuri follow Rentarou to an amusement park during a date with Yaku and Kishika, due to Kusuri’s belief that Kishika was trying to monopolize her grandmother. However, they quickly get distracted by the amusement park and end up doing their own thing (with the bonus page revealing that Kusuri’s actually forgotten why they came). At the end of the chapter, Kusuri technically catches Kishika in the act, but realizes that her real motive was to get Yaku to let Rentarou dote on her.
  • In Ah! My Goddess, Skuld discovered that her attempt at apologizing to her first serious crush was spied on by Keiichi and both her sisters. Urd just laughed it off, Keiichi tried to apologize while laughing nervously, but Belldandy looked positively mortified about what she was doing.
  • In Aizawa-san Multiplies, Nakamura, Ozeki, and Shiki watch the first date between Shino and Souta long enough to confirm that they're holding hands and thus moving forward in their relationship before leaving them to their date.
  • Angel Densetsu: Ikuko, Ikuno and Takehisa follow Ryoko and Kinato around during a date and work to ensure that it isn't interrupted. Their efforts were completely in vain, as every important character in the series then proceeded to show up to do just that.
  • In the eighth chapter of Asteroid in Love, animated in the third episode of the anime, Mira and Ao saw Moe and Mai walking around town acting like they were dating, although Moe quickly found out as Mira has been tweeting about it all the way. It's eventually subverted, since Moe and Mai are checking out an enclave of a neighbouring city on their own.
  • Case Closed: Sato and Takagi have a date in an Amusement Park with half the police force, trying to make it fail without being seen.
  • In A Centaur's Life, the main characters follow their friend Sasasuul on her date at an art museum. However, since she's an exchange student from reclusive Antarctica, she's also being tracked by security services and the three are almost picked up as terrorists.
  • Used in one of the early second season episodes of Code Geass when Lelouch and Shirley go to the mall together. Several of their friends from school follow them, since everyone knows Shirley has had a crush on Lelouch for a long time. Then there's the added twist that they are also being spied on by the Britannian government, since Lelouch is secretly Zero, a simultaneous Magnificent Bastard, Well-Intentioned Extremist, and Dark Messiah. Lelouch, naturally, proceeds to play everyone involved.
  • Eyeshield 21 plays with this. Sena finds a letter in his locker asking him to meet someone who is obviously a girl. Almost the entire Devil Bat team tries spying on him on this "date" for their own reasons. (The Huh-Huh Bros. can't believe Sena is getting some, Mamori is so happy to see him grow up, Suzuna is jealous, etc.) Turns out it's not a date, but a warning from their future opponent.
  • Full Metal Panic? Fumoffu has Kaname going on a date. Sōsuke and Kyoko, however, takes it up on himself to make sure she's not disturbed. While the two are observing the date dressed in suits and wearing shades, some Yakuza start molesting Kaname. Cue Sōsuke stealing his signature Bonta-kun costume and wiping the floor with the thugs without alerting Kaname to his presence — or so he thought; Kaname knew it was him when he shot one of the thugs out of habit then quickly stuffed the gun behind his back upon realizing it. She appreciated it anyway.
  • In episode 14 of Girls Bravo Fukuyama and Kirie follow Yukinari and Miharu around on their date.
  • GTO: The Early Years:
    • Shinomi, Ryuji, and their friends spy on Eikichi's karaoke date with Misato, and are surprised to see she's attractive.
    • Ryuji spies on his girlfriend Nagisa's date with Akira Saijo, even going so far as to hide under the seat of the Ferris wheel car.
  • Played all over the place in Infinite Stratos. Cecilia and Rin follow Charlotte and Ichika on a date. When Laura finds the peepers and is told what's going on, she shrugs and tries to just join the date, but Cecilia and Rin stop her.
  • Also a very common theme in Inuyasha. Most intimate moments between Inuyasha/Kagome and Miroku/Sango involve the rest of the team watching from the bushes.
  • In JoJo's Bizarre Adventure: Diamond is Unbreakable, the episode that introduces Yukako Yamagishi opens with Josuke and Okuyasu spotting her and Koichi on a date. They immediately hide behind a tree to watch and offer commentary on the situation.
  • Subverted in Kaguya-sama: Love Is War spin-off series We Want to Talk About Kaguya. Karen has the uncanny ability to always be nearby whenever Kaguya and Shirogane are having an intimate moment, but the one time she comes across them before anything happens she instead chooses to leave. As she notes to herself afterwards, coming across such things by accident is one thing, but actively waiting around like a stalker is just creepy.
  • Kaiju Girl Caramelise shows Rinko Akaishi disguising herself as "Mitchy", the Mocky Mouse mascot of Destinyland, when her daughter Kuroe goes on a date with Arata at the theme park. Initially, it was to confirm that it was in fact a date (Kuroe previously claimed she was just meeting some friends), but after seeing the date turn awkward thanks to Kuroe's efforts to avoid triggering her Involuntary Shapeshifting, she decides to covertly cheer things up between the two of them.
  • The date doesn't even have to be real to invoke this trope. In Kamen no Maid Guy, when Naeka goes to the festival with the leader of the Breast Fanclub, she has the other two Fanclub members, her Those Two Guys and both of her maids spying on her. Kogarashi attempts to boost the romantic atmosphere (and it works), but Fubuki misunderstands and ends up ending the whole thing by knocking the leader's head through a tree when she flings a lamp at him.
  • Happens in chapter 26 of Kimi ni Todoke, although Sawako and Kazehaya weren't officially on a date.
  • In Kitsune no Yomeiri, Ousuke, Kyouka, and Aria spy on lothario-mode Yoichi's date with Takoka Asuna to make sure he doesn't do anything to her. They in turn are spied on by Aria's brother Tarou, who thinks the three of them are becoming delinquents, only for him to be spied on by Kumi because she thought something interesting was going on. By the end of the chapter there are more than a dozen people spying on people who are spying on other people.
  • Happened in one episode of Kodocha when Sana, Akito and Tsuyoshi spied on Asako as she went out with a co star from one of her films, under the impression she was cheating on Rei. Hilarity Ensues and not everything is as it seems in the end.
  • Played completely straight in Ladies versus Butlers! by Sernia Iori Flameheart when her classmate and rival Tomomi goes on a date with her childhood friend Akiharu to resolve her feelings towards him. Not that it works much, seeing as the guy is an Idiot Hero with a bad case of Obliviousness To Love and a certified Marriage To His Job.
  • Also happens in Maison Ikkoku, with Godai's grandma behind it. It's hardly surprising that all of his neighbors took part, considering how nosy they all are. See a pattern here? Rumiko Takahashi apparently likes this plot.
  • Maken-ki!: In chapter 5, Himegami ropes Takeru into going with her to the mall. Haruko becomes jealous and disguises herself as a detective to spy on them and to make sure nothing happens. Inaho thinks it's fun, so she joins her, so does Usui due to wanting Himegami for himself.
  • In Maria Watches Over Us, Yoshino spies on the date between her grande soeur (and cousin) Rei and one of the winners of the Valentine's Day contest.
  • The Mermaid Melody Pichi Pichi Pitch manga nearly has this as a Running Gag with poor Rina and Hamasaki.
  • Parodied in a Mobile Suit Gundam SEED Destiny H-manga. As Athrun is about to snog Meer Campbell, several characters peek their heads in the doorway. When Athrun stops to look, they pull out cameras. His response is to shoot at them, which sends them scattering.
  • The friends of main characters Haruna and Masaru in Monkey High! have become pure kings of this trope, spying on them at all times and popping up inopportune moments, even following them around school.
  • Chapter 18 of Monster Musume (adapted as Episode 9 of the anime) has the girls tail Kimihito and Ms. Smith, spying on their date together. Turns out it's a cover to flush out an assassin out for Kimihito's life should he marry a monster girl.
  • A dark version occurs in My-HiME. Shizuru Fujino has abandoned her position as Student Council President to rescue and care for her best friend/unknowing love-interest Natsuki Kuga after she was injured in an ambush. Yukino Kikukawa, via means of her CHILD (which can generate camera drone-spores), knows where the two are. When her friend Haruka Suzushiro is desperate to find Shizuru, Reito Kanzaki (now possessed by the Big Bad suggests that Yukino tell Haruka where to find Shizuru. The two approach the house Shizuru is keeping Natsuki safe at, and, hiding behind the bushes, they witness Shizuru kissing a very unconscious Natsuki. This prompts an argument between the girls, where Yukino hints that the night before, her spy-cameras caught Shizuru doing far worse than just kissing Natsuki while she was unconscious and helpless.
  • In My Monster Secret, Asahi and a female character cannot go out anywhere or have a private conversation without someone spying on them; with the twist that the people spying are usually Shippers On Deck who planned the "date" in the first place. First, Youko plans to make Asahi and Aizawa go to the amusement park to spy on them, but fails. Then she (along with Shiho) succeeds in the summer festival. Later Karen and Akane conspire to make Youko and Asahi go to the amusement park, the same way Karen did for Youko's parents in the past. Even later, in chapter 100 Youko's mom and Akane use surveillance cameras to observe their (this time real) date and comment it like some kind of sports event.
  • This trope was used in Naruto Konoha Gakuen Hen, a comedic omake inspired by the second Naruto Shippuden ED which is set in a High School AU. Naruto goes on a date with Hinata and they're spied on by Sakura, Ino, Shikamaru, Chouji, Kiba, Shino and Sasuke.
    • When she's trapped by the Infinite Tsukuyomi Hinata's fantasy involves her having a date with Naruto, with her sister Hanabi and Neji (who'd just been killed by Obito) spying on them.
    • In Gaara Hiden, Temari spies on Gaara's "date" with his Hakuto, the woman Sunagakure's elders arranged for him to marry, wanting to see if everything is going well. To her surprise, it is.
    • In episode 497, Ino and Chouji are seen spying on Shikamaru and Temari's date through the window.
  • Negima! Magister Negi Magi:
    • This happens during Negi's date with Nodoka at the school festival; there were at least 5-6 other girls there watching 'em.
    • Earlier on, it's subverted. A couple of girls see Negi and Konoka and follow them around, thinking they're on a date. They even call the class president to inform her of what's going on, and she promptly drags both herself and Negi's roommate Asuna over to find out. Turns out that Negi and Konoka were buying birthday presents for Asuna.
    • Asuna's date with Takahata also has more than a few spies trailing along. Plus, Asuna and Negi's date in practice of that date had everyone aware of Negi's aged-self tagging along.
    • And Konoka's and Setsuna's "outing". Really, it would be easier to count the times Akamatsu hasn't done this.
    • He even took it to the next level; people seeing Date Peepers they know may decide to start spying on the spies, and in turn may be noticed and followed — to the point where almost nobody doing the peeping actually knows who's having the date, just that somewhere there is a date to be peeped on. It's implied to be so common as to be a standard Academy-wide student activity.
  • Oku-sama wa Mahou Shoujo has a beach episode where two people in a love triangle go out on a date. The third one isn't quite happy with that.
  • Otomen also has this, though it's justified because Juta is basing his story off of Asuka and Ryo's relationship.
  • Ouran High School Host Club has this in the episode/chapter Hikaru and Haruhi go on a date. The other Host Club members are wearing Paper Thin Disguises as they peep. In the manga the club members plan to spy on Tamaki and Haruhi's first date... in Paper Thin Disguises. Though in both dates, they do their best to help out the couple in question. And for Tamaki, they even stop the Zuka club from trying to ruin his date.
  • Persona 4: The Animation: The other party members peep on what they believe to be Yu's dates with multiple older women.
  • The Pet Girl of Sakurasou:
    • Mashiro and Jin get followed by Misaki and Sorata in Mahiro's research date (Love Hotel included).
    • And in episode 9, In episode 9, Mashiro and Nanami follow Sorata and Rita to a hotel. However, Rita realizes that they'd be following, so she greets them the instant they show up. Then she takes all of them to an art exhibit to show off Mashiro's final painting before she returns home to England.
  • Subverted in The Prince of Tennis, where the three times this trope is invoked... it's NOT a date, but something else. Ryoma and Sakuno went out only to get her racket fixed by a Cool Old Guy that Ryoma knew beforehand, a gorgeous girl that Kawamura was seen with once was the mother of his Forgotten Childhood Friend, and An only said she was in a date with Momo to keep him from running away from their friendly outing.
  • The Quintessential Quintuplets: When Fuutarou has his first official date with Yotsuba (as in, their first date after officially confessing and becoming a couple), the rest of her sisters begin to stalk them.
  • Ranma ½:
    • While Ranma and Akane have never technically been on a real date, whenever those two have a romantic (or assumed to be romantic) moment alone together at the Tendo's house, you can be sure that the Tendo and Saotome families are either spying or eavesdropping. They've also been real moment killers every now and then due to this.
    • A more specific example would include the time when Akane was tricked into going on a date with Ryōga. At first, she thought it was a challenge and that somebody wanted to fight her... then she finds out it's not and that Ryōga thinks it an actual date. Ranma shows up out of jealousy, pisses her off, she gives him the good ol' megaton punch, then decides that she really will go on a date with Ryōga. Ranma shows up out of jealousy again and tries to mess it all up. Hilarity Ensues.
    • Everybody has spied on Ranma and Akane at one time or another. The entire freaking school spied on them once.
    • When female Ranma goes on a date with an old man's spirit, Akane and the man's grandson follow them to spy. They watch from a bush, eventually.
  • In ReLIFE, while not quite a date, Hishiro and Kaizaki stay to watch Kariu and Ohga's confessions.
  • Happens a few times in Sailor Moon; the first movie starts with the team spying on Usagi and Mamoru.
  • SHUFFLE! has two potential love interests, one Handsome Lech, and one Camera Fiend set up a date for a couple. Don't expect them to let the date happen naturally.
  • SPY×FAMILY: In an Extra Mission chapter, Loid decides to take Yor out on a date, out of a wrong assumption that she's angry at him for something (in truth, she's only in horrible pain due to being Shot in the Ass during an asassination job). After they leave Anya with Franky to babysit her, the former convinces that they follow Loid and Yor, which Franky is all too eager to accept, even donning Paper Thin Disguises that Loid quickly sees through (but chooses to ignore).
  • The Story Between a Dumb Prefect and a High School Girl with an Inappropriate Skirt Length: In Chapter 25, Poemu's sister Ririku and Tougo's sister Kikuka secretly tail their older siblings to find out if they're dating.
  • In the first Tenchi Muyo! movie, Tenchi and his harem go back to the year 1970 to protect his parents from a time-traveling anomaly. While on a casual walk, the two are interrupted by Ryoko and Ayeka, who egg them on. Tenchi scolds them for risking a Grandfather Paradox.
  • In To Love-Ru Darkness, Nana, Momo, Mea and Yami all group together to spy on a date between Run and Rito. Shortly after, Yui also begins to spy on the two, though doesn't join with Momo's group.
  • Turns up in Urusei Yatsura, such as a date between Miko Sakura and bumbling dark wizard Tsubame. One Running Gag during the story was the watchers trying to find places to hide, only to find them already occupied by other couples trying to get a little heavy petting in.
  • When one of the girls in Wedding Peach tries to go out with the guy they are rivals for, the other two do this.
  • Yamada-kun and the Seven Witches: When the Supernatural Studies Club finds out using Maria Sarushima's future-predicting ability that Kentaro Tsubaki is currently predicted to accidentally start a cooking fire at the old school building, they decide to exploit his crush on Urara Shiraishi to keep it from happening. They figure out that Urara's body swapping ability is able to change the futures that Sarushima sees, so Ryu Yamada swaps with her and gets Tsubaki to go on a date. All the while, Miyamura and Urara-as-Yamada keep watch from a distance to make sure things turn out fine and to keep Yamada updated by phone on whether or not Sarushima's vision of the fire has changed.
  • You Like Me, Not My Daughter?!: After Ayako rejects Takkun, Miu tells her that he already got a girlfriend and has a date that day, telling her exactly when and where to make sure she follows them. Takkun spots her almost immediately, but it turns out he was seeing a movie platonically with his Crossdressing friend Ringou Satoya.
  • You're Under Arrest!: Miyuki and Nakajima's date in the third OAV. Small subversion in that the date was per orders of their boss, after a rather bad misunderstanding that involved them and Natsumi.
    • And further subverted in that Miyuki was fully aware that they were being watched the entire time. When the romantic moment is ruined by an All Officers dispatch call, Miyuki looks straight at the bush her partner is hiding in and tells Natsumi that they had better get going.
    • Perhaps played more straight in their dates afterwards, which usually have these not far behind; except in second season when Miyuki and Ken went to the amusement park with a mechanic's daughter. It was a change of plan which their would-be peepers are not aware of (The two originally planned to go to someplace else).
  • Yugami-kun ni wa Tomodachi ga Inai has Chihiro, Kuzumi, and Kadota checking in on Yugami during his date with Fujisawa.

    Comic Books 
  • Wonder Woman Vol 1: During the Golden Age the Holliday Girl's reaction to their leader Etta going on a date without giving them her plan for the night is to load up in Glamora's jalopy and follow her. This proves very annoying for Etta when they misinterpret her leaving on an espionage mission to try to help Steve Trevor, whose been compromised, as her trying to go on a date with Steve and follow.

    Fan Works 
  • In Chapter 59 of BlazBlue Alternative: Remnant, when Yang and Pyrrha go out on their first date, Ruby opts to follow and keep an eye on them, saying that she wants to protect them from Grimm attacks. Penny quickly surmises that she just wants an excuse to spy on her sister's date, but goes along with it. Their spying ultimately goes nowhere and is never found out since Penny gets distracted by fireflies in the middle of it and Ruby follows along, leaving Yang's date unwatched.
  • Briefly discussed in A Delicate Balance. Pinkie expresses her intent to follow Applejack and Twilight on their date, but ultimately gets talked out of it by Rarity.
  • A Divine (Romantic) Comedy:
    • Luz and Vee insist on spying on Camila's first official date with Lucifer/Lucius, both to document it and in case Lucius isn't what he seems, with Masha getting dragged along to keep the two of them out of trouble. Unlike most examples, Camila's completely aware of this from the get-go and shrugs it off, only caring that her daughters don't cause too much trouble while they're doing it, though she does get a little frustrated when Vee takes the form of a stereotypical French waiter to intervene during an awkward moment.
    • Charlie also gets in on things by sending Dazzle to monitor the date and report back to her, wanting to make sure that Camila isn't a Gold Digger or something.
  • First Date is a The Owl House oneshot that is, as the name suggests, about Luz and Amity's first date after their Relationship Upgrade. Eda, with Hooty and King in tow, decides to follow them to keep an eye on things, with Edric and Emira independently deciding to do the same, and Gus and Willow getting dragging into it once they cross paths with the two groups (though Willow only tags along to keep the others out of trouble after failing to talk them out of it). At the end of the story, the couple reveal that they knew they were all there all along, with Luz stating that she appreciates them all caring enough about their relationship to do it.
  • In Ranma ½ story Girl Days, female Ranma is obligated to go on a date with Ryoga due to a dumb dare and even dumber happenstances. Akane, Shampoo and Ukyo know their "date" doesn't mean anything but they still intend to spy on them.
    Three young suitors for the hand (and other parts) of one Ranma Saotome.
    Three people who KNEW that this so-called date was totally innocent, meant nothing, and should just be shrugged off as another case of weird male macho stubbornness.
    But... just in case...
    Three people who were, quite independently, planning to monitor the date, for Ranma's safety, of course, they weren't going to interfere, of course not, farthest thing from their minds, and besides, if I don't keep an eye on them who will because I can't trust the OTHER two to come to the rescue if Ryoga or Ranma goes whacko...
  • In The Legend of Miraculous, Ravio follows Link and Zelda outside in hopes of seeing Link confess his feelings to her. Hilda refuses to join him, claiming to be above snooping, but she offers Ravio her phone so he can record it for her in HD.
  • MLP Next Generation: Know Fear!: When Starburst and Golden Delicious admit to their feelings for each other and go on a date, their friends Claire, Cotton Candy, Prism Bolt and June follow them (though the latter's only there to keep the first three from interfering). And it turns out that Star and Del knew they were there the whole time, they just ignored them.
  • Averted in Non-Date. This is what Nora and Yang think they're doing. In reality, they're just watching two friends hang out together.
    Blake: Hold on. How do we know this is a date?
    Yang: How do we know that it isn't?
  • The core of the My Little Pony: Friendship Is Magic fanfic Once Bitten, Twice Shy's humour lies in the Gambit Pileup between two vastly different sets of Date Peepers trying to give Twilight and Fluttershy help on their dates. Fluttershy's team: a down-to-earth farmer and a sophisticated dressmaker. Twilight's: a reckless speedster and a lunatic who is literally too weird for magic to explain. Is it any wonder everything went to Yeah That Place?
  • In the 2020 Holiday Special of Pokémon Reset Bloodlines, Ash's Butterfree prepares a gift for Viv, the Vivillon who's recently become his Second Love after he left the Pink Butterfree behind. Squirtle and Bulbasaur help him wrap the gift, and latter hide in a bush to check how things go (and to make fun of Viv's nickname for Butterfree, "Butt").
  • In a chapter of Pripara Forever, Nina, Fumika, Chululu, and Sun sneak up on Lucien and Isania's date.
  • Scarlet Lady: When Adrien, Nino, Marinette and Alya all head to the zoo together, Chloé follows them, complaining about how "her Adrikens" chose such an unpleasant and unimpressive place for a date.
  • Sparkling Shimmer: After catching Twilight and Sunset out on a date, Pinkie drags the rest of the girls out to spy on another one. As a result, Rarity ends up being a Moment Killer to what would have been Twilight and Sunset's first kiss. Needless to say, Sunset is angry.
  • Very frequently in There's More Magic Out There, with the cast's monster powers involved.
    • At the end of the first chapter, Alya, in her fox form, spies on Juleka and Rose when the two are together. After Rose points out the fox, Juleka chases her fellow monster away.
    • Downplayed with Kagami in chapter 12, who watches Marinette and Adrien in her cat form while the two are only hanging out and not dating. She runs into Juleka who was doing the same... in her dire wolf form.
    • In chapter 29, Juleka is on a date with Rose and is conflicted if it's okay to kiss her after finding out they've been dating for months. She suddenly hears Alix's voice yelling in her head to just kiss Rose already, revealing that the witch was watching them the whole time.
  • A running gag throughout the Time Fixers: Nicktoons of the Future series.

    Films — Animation 
  • Batman: Mask of the Phantasm: Batman watches Andrea and Arthur Reeves while they're on a date. Gotham's gargoyles once again provide excellent cover.

    Films — Live-Action 
  • The "lovely" date between Darla and Alfalfa (including sabotage by the members of the gang) in The Little Rascals movie.
  • Vada and Thomas J follow Vada's Father and Shelley on the Bingo date in My Girl. She yells "Bingo!" in from the window and Hilarity Ensues.
  • A highly comedic subversion happens in Shoot 'Em Up. The baby alerts the hero to the presence of multiple hitmen during sex with his Love Interest. He ends up dealing with them all without breaking stride, so to speak.
  • Stargate: When Daniel has a sensitive conversation with Shau'ri and admits his attraction by sharing a long kiss with her, two local boys look in on them, apparently highly amused at this development.
  • A variation in Wasabi: as Jean Reno's Disappeared Dad character, Hubert Fiorentini, and his daughter are on a bonding Shopping Montage, they are followed around by the Yakuza men. Hilarity Ensues as Hubert uses creative ways to deal with them without her noticing.

     Music 

    Literature 
  • The Hound of the Baskervilles: Sir Charles goes out on the moor and stops Watson from accompanying him, as he's going to see Stapleton's sister. Watson, torn between his duty to keep guard on him and his morals preventing him from being a Date Peeper, settles for waiting on a nearby hill, where he can see without hearing things a gentleman should not be aware of. However, the wooing is interrupted by a furious Stapleton, sufficiently so that Sir Charles takes a humorous view of Watson's behavior. It's also a vital clue that Stapleton's sister is actually his wife and reluctant accomplice.
  • Princesses of the Pizza Parlor: "Princesses on the Lonely Isle": Discussion of a parent peeping on their child, instead of a friend doing the peeping is had:
    Uncle: And the hedges by the window are too small for your dad to hide behind, so no worries there."
    Her father had a laugh to rattle silverware.

    Live-Action TV 
  • 7th Heaven: The Camden family are close to being the Trope Codifier, as frequently they (pick any member) would sneak into their own family members or other people's dates to see their business, often becoming a Moment Killer. The family has never heard of "privacy".
  • Carly and Sam do this in iCarly with the use of a webcam when Freddie has a date.
    Carly: (while she and Sam are eating berries) We're bad people.
  • During the big field trip finale movie of Ned's Declassified School Survival Guide:
    Crony: Would someone just kiss someone already!?
  • Our Miss Brooks:
    • In "Madame Brooks Du Barry", Mr. Conklin and his daughter Harriet hide in the back of Mrs. Davis' living room, and spy on Miss Brooks and Mr. Boynton as they have a date.
    • In "Mrs. Nestor's Boyfriend", Miss Brooks, Mr. Munsee, Mr. Talbot and Mr. Conklin use binoculars to spy on (widowed) Mrs. Nestor's date with her new boyfriend.
  • Parks and Recreation has a twist on this. Leslie and Ben think that Ann and Chris are going out on an illicit date (Chris is Ann's boss and fraternization is forbidden), so they trail Ann to a restaurant, peek in the window—and find out that Ann is dating Tom.
  • In Power Rangers: Dino Thunder, the other Rangers use their surveillance equipment to spy on Ethan as he has his first date with Cassidy. When things start going wrong, Tommy Oliver actually uses his invisibility power to provide assistance.
  • Luke, Rani, and Clyde in The Sarah Jane Adventures episode "The Wedding of Sarah Jane Smith", although they don't know that it's a date at first. They thought she was hunting aliens.
  • Supernatural: Dean does this to his own parents, yes in a Back to the Future homage, when he is sent back in time. His mom, Mary, clocks him and confronts him. Leading to Dean discovering his mom was raised a hunter.
  • White Collar: Peter has to pretend to be a wealthy bachelor as part of a sting to catch Black Widow Selena. When she suggests they go to his place, he panics (since that would probably result in her figuring out that he's married), so he takes her to Neal's apartment instead, calling ahead so he can commandeer Neal's dinner with Sara. Neal and Sara get the call at the last minute and sneak into a side room to spy on Peter and Selena.

    Video Games 
  • The King of Fighters:
  • This is the entire premise of Kitty Powers' Matchmaker, where the player watches their clients' blind dates through hidden cameras and offers advice through the client's earpiece. This is expanded in Love Life, where the player checks their villagers' KittyFeed to read their status updates.
  • The Legend of Heroes: Trails of Cold Steel IV has Rean inadvertently peep on Olivert and Schera's mini-date at Mishelam and Olivert asks for Schera's hand in marriage. Inadvertent because Rean got there first before Schera and Olivert showed up though they weren't near him but their voices were loud enough that he could hear the two of them.
  • The first appearance of the gym leader Misty in Pokémon Gold and Silver has you interrupting her date in Route 25.
  • Not quite a date, but Anastasia and Joachim spy on Yuri and Karin during their blossoming romance in Shadow Hearts: Covenant. Anastasia is rooting on Yuri to kiss her, which he fails to do, and since she turns out to be his time-traveler mother, so much the better.
  • In Tomodachi Life, it's possible for a Mii to want to set two other Miis up together. The first Mii will then spy on them all throughout their date.

    Visual Novels 
  • Cafe Enchante:
    • Played with during Il and Kotone's outing as Misyr is more concerned about the hermit Il going out and is worried Il might (and he did) unwittingly reveal his powers to humans.
    • Played straight in Rindo's route where the other regulars were revealed to be watching Rindo and Kotone from a distance and deliberately called his cell phone during an intimate moment to stop them from kissing.
  • Kyou Fujibayashi has a tendency to do this in CLANNAD. She pretty much orchestrates the entirety of Tomoya's relationship with her sister, either from the shadows or more commonly directly, but she also interferes on Kotomi's route.
  • Fate/hollow ataraxia: Caster ropes Shirou into following Taiga and Souichirou, to see if Souichirou is cheating on her. When Shirou asks why he had to be involved, Caster says that if the police caught her following them alone, she'd look like a jealous mistress. Shirou points out that she and Souichirou are legally married, so the cops would be on her side for this. She had completely forgotten about that. Of course, it was blatantly obvious from the start that Souichirou wasn't cheating on Caster, so the whole thing was unnecessary.
  • Grisaia Series: The female cast of Mihama Academy is rather easily susceptible to this kind of behavior, no matter which heroine the protagonist ends up with.
    • In Fruit, on Sachi and Yuuji's date, Amane is the one who was curious about how they were doing.
    • In Labyrinth, in Amane's after story, the entire rest of the group decides to stalk Amane and Yuuji to their date out of curiosity (and because they were a bit jealous, also bored).
    • Also in Labyrinth, in Yumiko's after story. Although it was Yuuji who invited the girls to join them at the end of their date, they still managed to spy on them at the most inappropriate moment.

    Web Animation 
  • In the Homestar Runner cartoon "Date Nite", Homestar and Strong Bad sneak along on Marzipan and The Cheat's date, and try (and fail) several times to sabotage it.

    Webcomics 

    Western Animation 
  • Danny Phantom: Both Danny and Sam spy on each other with their respective date with assumptions that their not-quite-not-yet-significant-other is up to no good. Not in the same episode.
  • Happened in an episode of Doug where the entire non-adult cast spy on Doug and Patty's first date.
  • Family Guy:
    • An episode has Peter going into Boyfriend-Blocking Dad mode and infiltrating Meg's date dressed as a stereotypical Chinese man.
      Meg: Dad, what are you doing here!?
      Peter: Pee-tah? Who Pee-tah?
      Meg: I didn't say "Peter", I said "Dad".
      Peter: Ooohh.
    • Brian and Stewie also intruded at a date between Meg and Mayor West in an attempt to bring him down with a teenage sex scandal.
  • Hey Arnold!: Helga loves doing this to Arnold.
  • My Life as a Teenage Robot:
    • Jenny, Brad, Sheldon and Tucker all spy on Nora Wakeman during her dates in "Mama Drama", though Nora isn't really trying to keep her romantic life secret.
    • Sheldon goes to great extents with this when Jenny has a date.
  • In the OK K.O.! Let's Be Heroes episode "My Fair Carol", the main trio of K.O., Rad, and Enid spy on the date between Mr. Gar (their boss) and Carol (K.O.'s mom). This is mainly because they're trying to help Carol have the "perfect date" with Gar and are keeping watch to make sure everything's going okay, and Carol knows they're around. At the end, though, the three of them play this even straighter when watching Carol and Gar kiss from nearby.
  • In The Replacements, Reilly's entire family (including the talking car), spy on her first date, even going so far as to impersonate the wait staff in the restaurant.
  • The Steven Universe episode "We Need To Talk" has the Gems spy on Greg and Rose while they're trying to do a Fusion Dance. Amethyst doesn't even bother to hide herself and just waves at them when they are spotted.
  • In an episode of W.I.T.C.H., Elyon is annoyed and ultimately driven to tears when her friends ruin her date with a new beau by constantly interrupting them because they think he's a monster in disguise. Turns out, he's not. Not that they were particularly subtle about it.

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