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- One chapter of Sgt. Frog has Momoka trying (and failing) to work up the nerve and/or find the opportunity to offer her crush Fuyuki some home-made chocolates on Valentine's Day. Meanwhile, Fuyuki earns the jealous ire of his classmates when all the girls in the school keep giving him chocolate. He's profoundly disappointed when he finds out all the chocolates are intended for his sister Natsumi, and equally delighted when Momoka shows up at his house with her gift of chocolate.
- An episode of the harem comedy Ai Kora has Maeda trying to smuggle home a chocolate statue made in the shape of a girl with all his "ideal parts". Unfortunately it's on Valentine's Day, and all the girls he knows try and ply him with chocolates (and lots of it, in the cases of Ayame and Kirino). He eventually eats so much chocolate he passes out, and awakens to find his chocolate sculpture has melted.
- One episode of Yo-kai Watch has both of Nate's male friends getting confessions and chocolates from a girl on Valentine's Day. Nate becomes jealous and ilogically assumes that the reason they got chocolates from girls and he didn't is because a Yo-kai's screwing with him. He's right.
- A recurring running gag in every Valentine's Day chapter in Urayasu Tekkin Kazoku which Kotetsu always demand chocolate from Akane.
- Wandering Son had at least one Valentine's Day chapter in middle school. Mako tries to give Oka a "friendship chocolate" but Oka gets grossed out.
- Episode 31 of Nurse Angel Ririka SOS is a great demonstration of the "obligation chocolate"/"true feeling chocolate" dynamic in action, and features Ririka's friend Karin as she gets confessed to by a boy from school that she had never given any thought to before.
- The Hack/Slash and Bomb Queen crossover was supposed to be this, though apparently due to delays causing it to be released after February the holiday aspect was dropped.
- Marvel once produced a number of I (Heart) Marvel one-shots; the Spider-Man themed one, "Web of Love", was all about Spidey trying to think of a good Valentine's Day present for his wife, Mary Jane. In the end he had Tony Stark make a pair of web-shooting bracelets for her.
- The Books of Magic had a Valentine's Day story called "This Is Not About Chocolate", in which Eros/Cupid attempted to strike back against his modern image as a cherub in a nappy (and by analogy, the comercialisation of romance in general).
- Issue #24 of The Powerpuff Girls, "The Bride Of Mojo Jojo," had Mojo seeking love on Valentine's Day. But when a dating service fails him, he uses material from discarded weapons and his own DNA to create his own bride a la The Bride Of Frankenstein. The girls, in a subplot early on, entertain ideas of what kind of mother they'd want.
- Issue #12 of Ms. Marvel (2014), there is a Valentine's day ball, and Bruno tries to invite Kamala to it... even this would spell disaster, but Loki also arrives and has way too much fun Playing Cyrano (badly), spiking the punch with Truth Serum, and being as much of a troll as possible in general.
- Script Fic Calvin and Hobbes: The Series has "Insanity is In The Air", which gave some Character Development to Andy.
- Misa and the Bear is a humorous Death Note Crack Fic where Light has to contend with Misa, his harem of cover girlfriends, L, and Ryuk's misunderstanding of the holiday. Needless to say things don't go as planned.
- The Facing The Future Series has "What She Wants", which features Desiree and Sidney Poindexter, of all people, getting together.
- The Empath: The Luckiest Smurf series has two of them:
- The story "Hefty, The Luckiest Smurf" begins on Valentine's Day, with Empath giving Smurfette the present of a mock wedding ceremony in the Imaginarium with Hefty as her imagined bridegroom. The rest of the story centers on Empath seeing Smurfette in an alternate timeline falling in love with and marrying Hefty when Empath is forced to return to Psychelia, and how he deals with it after he finds out.
- "My Unsmurfy Valentine" also takes place on Valentine's Day, on which the rogue cherub Eros decides to ruin it by firing lust arrows that make whoever's struck by them lust after whoever they desire, even if it's of the same sex.
- The main premise in Hunting the first fic of The Matrix and Supernatural crossover slashfic Hunting Series is Dean forgetting it's Valentine's Day, until Neo remindes him of it. Eventually, it ends up kicking off one of the main pairings, the One True Threesome, of the series.
- The sixth episode of The Child of Love is a Valentine's Day chapter. Asuka tries to give Shinji some home-made chocolates on Valentine's Day without everybody noticing.
- The One I Love Is: The story begins during a Valentine's Day. As Asuka is trying to work up the nerve to give Shinji some home-made chocolates, Rei gives Shinji a chocolate box, earning Asuka's wrath and kick starting the plot.
- Older Than Print: The first known connection between romance and Valentine's Day was made by Geoffrey Chaucer.
- Harry Potter has had two:
- In Chamber of Secrets, Lockhart sets up an ill-conceived Valentine's celebration which annoys everyone but himself. Ginny sends Harry a singing valentine using Lockhart's "card-carrying cupids", but it backfires badly.
- In Order of the Phoenix, Harry takes Cho Chang to a date on Valentine's day. This also doesn't go so well.
- The Savannah Reid Mysteries book Sugar and Spite. Savannah laments somewhat over the fact that her only Valentine's Day plan is to assist her cop buddy Dirk with a stakeout. When Dirk's ex-wife shows up and is murdered with his gun, Savannah spends the days leading up to the holiday working to clear his name and find the real killer, comforting Dirk along the way and realizing, not for the first time, that her feelings for him might be a little more complicated than just friendship. At the end he thanks her for her support by splitting a heart-shaped box of chocolates with her.
- Junie B. Jones and the Mushy Gushy Valentine has Junie B. trying to figure out who sent her a Valentine during the school's Valentine's Day Party. It was Jim who secretly has a crush on her.
Live Action TV
- Arrested Development: 'Marta Complex' has a Love Triangle between the titular Marta and brothers G.O.B. and Michael.
- The Big Bang Theory: "The Large Hadron Collision" has Leonard going to CERN and seeing the LHC. He has a plus one and since it will be Valentine's Day would like Penny to accompany him. Sheldon has other ideas.
- "The Locomotion Manipulation": Sheldon and Amy go with Howard and Bernadette on a train ride to Napa Valley. Amy planned on a romantic dinner, but Sheldon would rather talk trains with a complete stranger, leading to an argument which ends with Sheldon and Amy's first kiss. Meanwhile, Leonard and Penny spend Valentine's Day baby-sitting Raj's dog, which eats the box of chocolates Penny brought Leonard and have to take her to the vet, who develops a thing for Raj.
- Buffy the Vampire Slayer: "Bewitched, Bothered and Bewildered". Xander concocts a Love Potion to use on Cordelia so he can dump her in the most spectacular fashion possible, but it backfires. Angelus intends to use the holiday and his history with Buffy to inflict a good dose of Mind Rape on her, but Xander's problems ruin his plans.
- "Crush". Buffy discovers Spike is in love with her. Things go downhill from there.
- Charmed: "Animal Pragmatism" from season 2, in which Phoebe accidentally enables a bunch of her college buddies to cast a spell that turns animals into hunky (but slightly evil) guys.
- Community the first season has 'Communication Studies' and second season has 'Early 21 century Romanticism'.
- Criminal Minds: "Closing Time". The Bartender who hears everybody's sob stories decides to put the storytellers out of their misery, while Hotch's relationship with his triathlon training partner grows.
- Family Matters "My broken-hearted Valentine, Heart strings and Le jour d'amour".
- Full House "Little shop of horrors, The heartbreak kid and Dateless in San Francisco". Also, Jesse and Becky's wedding is on Valentine's Day.
- Grey's Anatomy, the February Day episode reminded two of the doctors that they were single and they proceeded to make out in the closet.
- Happy Days, the musical montage episode "Be My Valentine."
- The Middle Four episodes as of the fourth season. Like all of their holiday episodes, these episodes are named Valentine's Day, Valentine's Day II, etc.
- Nicky Ricky Dicky And Dawn has the episode "Valentime's Day". The four kids work to cheer up Tom and Ann before Valentine's Day, Or Valentime's Day as Dicky keeps calling it.
- The Office: "Valentine's Day" in the second season and PDA in the seventh season.
- The Pretender had a Valentine's Day episode in its second season. It was Jarod's first experience of the Day, due to his deprived childhood.
- Punky Brewster. She disavows Valentine's Day then dreams she is an elderly spinster.
- Sabrina the Teenage Witch
- Season 1 - Sabrina and Harvey's first kiss turns Harvey into a frog. And she must prove that it's true love to turn him back.
- Season 2 - features Cupid and Mr Kraft fighting over Aunt Hilda, while Sabrina gets magicked into falling in love with Roland the troll.
- Season 3 - Sabrina has to make Cousin Marigold fall in love with a mortal handyman.
- Season 4 - Sabrina discovers that Josh is in love with her and - because she already is with Harvey - she comes down with something called 'Candy Hearts Syndrome'. And must make Josh fall out of love with her.
- Season 5 - Josh and Morgan are on the verge of breaking up - and Sabrina is conflicted by her own feelings for Josh.
- Shining Time Station has the episode, "He Loves Me, He Loves Me Not". Valentine's Day is held at the station, and Mr. Conductor becomes Cupid's helper. However, his magic dust accidentally makes Stacy Jones fall madly in love with Schemer, to the point where the two nearly end up marrying each other.
- Smallville: In the episode "Persuasion", Clark is exposed to wish fulfilling gem-kryptonite on Valentine's Day and wishes for a more traditional relationship with Lois.
- Also during "Crimson", Lois is given some red lipstick which makes her fall for the first guy she sees, Clark (who she wasn't dating at the time).
- Supernatural: "My Bloody Valentine" from season 5. It focused on desires rather than love, as the Horseman Famine's arrival in a town causes everyone's desires to go overboard. Sam starts craving for demon blood, Castiel starts consuming hundreds of burgers, but Dean is unaffected, which Famine speculates is because he has become empty inside.
- 30 Rock Liz Lemon does not have the best of luck on Valentine's Day.
- In the series' first Valentine's Day episode, "Up All Night", Lix tries to figure out who sent her flowers.
- In "St. Valentine's Day" Liz goes on a disastrous first date with Dr Drew Baird. Meanwhile, Jack and Elisa spend the evening in church.
- "Anna Howard Shaw Day" in the fourth season had Liz boycotting Valentine's Day, choosing to celebrate the birthday of suffragist Anna Howard Shaw instead, and scheduling a root canal for that very day. Naturally, things don't go according to plan.
- "Double Edged Sword", the fifth season's Valentine's Day episode, looks at the effects of being a relationship with someone very similar in personality.
- "Hey Baby, What's Wrong?" Liz and Criss' relationship is put to the IKEA test, while Frank and Tracy teach Lutz their dirtbag knowledge on how to pick up women.
- Peanuts dependably focused on Charlie Brown never getting any valentines.
"I know nobody likes me... why do we have to have a Valentine's Day to emphasize it?"
- Calvin and Hobbes had a series of comics about Valentine's Day every year during its run. These tend to focus on Calvin's and Susie's nascent crush.
- WCW Clash of Champions V: St. Valentine's Day Massacre (the other Clash of Champions were not examples)
- JAPW Valentine's Day Massacre '98 (after 99 they stopped including years in the titles)
- NJPW Fighting Spirit - Day 15 - St. Valentine's Day Massacre (noticing a pattern yet?)
- WWF In Your House 27: St. Valentine's Day Massacre (We'd be here for years if we listed all the wrestling events named after that event)
- Triple X Wrestling in the UK had an event called Chop Him In The Valentines where Legion Of Womb (Jetta and Skye) had the opportunity to do just that to Chris Charizma and JP Monroe.
- The wacky Dramatic Dream Team's DDT Non Fix Valentine Special, with a Valentine Special Single Match right before the main event.
- NWA Wisconsin and NWA On Fire have Valentine's Vendetta(apostrophe varies year to year). Thematically appropriate matches? Frakie DeFalco defeating Brandon Haze and Stacy Shadows in a handicap match.
- Defied at AWS No Time For Valentines Love
- Coastal Championship Wrestling's Valentine's Vengeance. One of the most appropriately themed matches had Pablo Márquez going over El Guapo and Rico Casanova.
- Our Miss Brooks has two Valentine's Day episodes, both on the radio:
- The Frog sees Miss Brooks adopt a pet frog, in an effort to set up a "double date" with Mr. Boynton somewhere outside the zoo. It makes sense in context.
- Valentine's Day Date see Miss Brooks again try to keep Mr. Boynton away from the zoo. This time, she uses a gift certificate provided by Stretch Snodgrass to lure Mr. Boynton to Turk's Turkey Heaven. Hilarity ensues.
- In Persona 4 Golden, near the end of the game, you get to take part in one of these and spend a romantic afternoon with your girlfriend at Shichiri Beach, but there's a twist. If you've gotten into relationships with multiple girls, then you can only choose one, and must personally reject each one you didn't pick. If you don't take someone out, you end up at Junes with the guys from the party.
- The visual novels produced by Voltage Inc frequently put out holiday-themed side stories at appropriate times of the year, and Valentine's Day episodes for February are particularly common:
- Pirates in Love has the "Valentine Kingdom" side story, in which the crew of the Sirius visit a Valentine-themed country.
- 10 Days with My Devil's "Black Valentine's Day" side story involves introducing the demons to the concept of Valentine's Day as celebrated in Japan, and their occasionally comical efforts to understand it.
- There's also the "A Royal St. Valentine's Day" side story in Be My Princess, the "Your 1st Valentine's Day" story in My Forged Wedding, and the "St. Valentine's Day" side story in My Sweet Bodyguard, which all focus on the heroine trying to have a romantic Valentine's Day with her boyfriend in the face of various obstacles.
- In the Homestar Runner short "Sickly Sam's Big Outing", the Old-Timey versions of the cast try to find Sickly Sam (Old-Timey Strong Sad) a girlfriend, and Old-Timey Strong Bad tries to bait Sam into a Prank Date so he can sell him to the glue factory. It ends with Strong Bad getting swallowed whole and Sickly Sam going out with a broken-down horse.
- Teen Girl Squad. "Issue 12" involves the girls trying to find dates for the big day. What's Her Face finds true love with the Wireless Wizard, the other three girls die. The episode is "drawn" in red pen for the occasion.
- xkcd: Is fond of mixing love and science for Valentine's Day comics. #63, #223, #543, #701.
- Saturday Morning Breakfast Cereal: Had this couple strengthen their relationship on Valentine's Day.
- Electric Wonderland: "Valentine's Day Massacre" has the three main females argue over a guy and make fools of themselves in the process. The comic itself never refers to Valentine's Day by name.
- This kicked off a tradition of Platypus Comix having a new Valentine's comic every year.
- Narbonic: The Demons story arc, which actually took place around Valentine's Day in the original run. Helen decides to have an office party on Valentine's Day. Mell is the only one to bring her own date (recurring character Seth, albeit at gunpoint so she could win a bet with the rest of the office), and Helen and Dave step outside for a serious talk... to be interrupted when Caliban flies naked face-first into a nearby snowdrift out of the sky, demonic loan sharks invade to take him back (and take the the rest of the lab if they can, starting with Seth), and hilarity generally ensues. On the romantic side, Mell and Caliban do become an item after this.
- Welcome to Night Vale has an episode set in the aftermath of Valentine's Day. Apparently mass casualties, the obliteration of whole suburbs, and holiday cards that require specialist disposal squads are all normal features of Night Vale Valentines celebrations, and as such, the holiday is dreaded yearly.
- Will It Blend? has the episodes "Annoying Valentine's Gift" and "Valentine's Day Roses".
- Stuart Ashen has done a few Valentine's Day episodes which involve reviews of products from British retailer Poundland.
- Thrilling Intent has a "Velafitine's Day" episode in which Markus Velafi serenades his friends.
- The Super Mario Logan episode, "Mario's Valentine's Day Problem!" focuses on Mario having to choose between Rosalina and Peach when the latter wants to spend Valentine's Day with him.
- DuckTales: Two episodes:
- "Back to the Klondike" Scrooge goes back to his claim in the Yukon, meeting his old girlfriend, Goldie.
- "A DuckTale's Valentine": Having been stuck with a magic arrow, Scrooge falls in love with Aphroducky, the mythological Goddess of Love. This is considered one of the less popular episodes of DuckTales, and that's an understatement.
- The Cleveland Show has a few of these episodes, such as "There Goes El Neighborhood" and "Here Comes the Bribe".
- Ed, Edd 'n' Eddy's Hanky Panky Hullabaloo was a special in which a pair of mischievous cherub versions of Sarah & Jimmy caused Edd and May Kanker to fall in love. Hilarity Ensues as their lovey-dovey exploits drive the other Eds and May's sisters up the wall.
- Blue's Clues: Featured in an episode, though in a similar fashion to You Mean "Xmas", they refer to the holiday as "Love Day".
- On Daniel Tiger's Neighborhood, there's a two part episode on their version of Valentine's day called "Love Day".
- There's a Valentine's Day episode of Martha Speaks called "Martha and the Thief of Hearts".
- Family Guy had a Valentine's Day episode focusing on many characters and their love-lives, a la Valentine's Day to the point of making fun of its trailer in place of the opening sequence.
- "Put Your Head on My Shoulder" focuses on a Fry/Amy relationship. Just as Fry decides to break up, they get in an accident and Zoidberg has to graft Fry's head onto Amy's shoulder to keep him alive.
- In "Love and Rockets", Planet Express gets a lucrative job transporting candy hearts, while Bender starts dating the Planet Express Ship's computer, then chooses the worst possible time to break up with her. The whole thing plays out as a very strange parody of 2001: A Space Odyssey. The episode also features some Ship Tease for the Will They or Won't They? relationship between Fry and Leela.
- Johnny Bravo had a Valentine's Day special, where it's revealed that Johnny was born on February 14. It had him finally meet a woman who likes him, only she turns out to be a secret agent.
- Peanuts had a few Valentine TV Special, including "Be my Valentine, Charlie Brown" and "A Charlie Brown Valentine".
- The Simpsons:
- After the actual death of Ned Flanders' wife, Ned at a Valentine's Day dance became conscious of the fact, thanks to Homer speaking out loud about the fact its a day for couples.
- Another Simpsons example, Homer and a bunch of other married men got mad at Apu for making them look bad one Valentine's Day by his over-the-top romancing of Manjula - getting Elton John to sing for her, etc.
- "I Love Lisa" focuses on a crush Ralph Wiggum has on Lisa.
- The Spectacular Spider Man: Gangland in season two has a huge group date...and a mobster summit where Hammerhead betrays Tombstone/The Big Man, and a three-way fight between Tombstone, Silvermane, and Doc Ock breaks out. The Green Goblin put Hammerhead up to it.
- SpongeBob SquarePants had a story where he schemed to get the best Valentines Day present ever for Patrick. Things go wrong, Hilarity Ensues.
- Recess had "That Stinking Feeling" and "My Funny Valentines" paired together for airing. "That Stinking Feeling" was about Spinelli's crush on a boy, while "My Funny Valentines" (which is the more official Valentines episode) was about T.J. making joke Valentine cards for the girls of the school, but with them thinking that he had crushes on him. Ship Tease ensued between T.J. and Spinelli (again). Oddly enough, the episode didn't air anywhere near the holiday (though the show is usually in it's off-season in February)
- Doug's 1st Movie was set around Valentine's Day, centering around a Valentine's Dance.
- The series doesn't have an official Valentine's Day episode, "A Nut In Every Bite!" (where Henry falls in love with Dawn, the network executive's granddaughter) was usually re-ran in February.
- An Off-Beats Valentine (based off a recurring segment on KaBlam!) had Tommy and Populars member Beth fall in love with each other, but they had to keep it secret. Subplots involve August trying to find love the "unplugged" way, and his dog September reminiscing over his love of a cat named February.
- Rugrats had a Valentine's Day two-parter. The first half involves the babies trying to get Spike and Fluffy to fall in love with each other, and the second half involves Chuckie making a valentine for his dad during the Valentine's Day dance.
- The My Little Pony: Friendship Is Magic episode 'Hearts And Hooves Day', in which the Cutie Mark Crusaders try to get Cheerilee and Big Mac together using a Love Potion. It doesn't go as well as they'd hoped.
- 101 Dalmatians: The Series had "Valentine's Daze", showing Cruella's dislike for the holiday as she has no one to be her Valentine.
- Tex Avery's 1936 Merrie Melodies cartoon "Don't Look Now" had Dan Cupid preparing for Valentine's Day with his bow and arrows, while the Devil (like Cupid, depicted as a kid) prepares for the day by messing things up for couples-to-be.
- A Scooby-Doo Valentine (a special episode of What's New, Scooby-Doo?) has the gang on Valentine's Day framed for crimes committed by four people who are their lookalikes. They are unmasked at the end as cartoon likenesses of the gang's voice actors—Frank Welker, Casey Kasem, Grey DeLisle and Mindy Cohn. Additionally, the leader of the group is former *NSYNC member Special Guest J.C. Chasez... dressed as Scooby-Doo.
- The animated Punky Brewster had "Be My Glomley." On Valentine's Day, Glomer discovers Glomine, a girl glomley, and with their combined powers can create a gateway back to Chaundoon. It almost works, except when Punky is seen dangling from a hot-air balloon basket, Glomer sacrifices his ticket back home, sending Glomine back, in order to rescue Punky.
- The Smurfs cartoon show special "My Smurfy Valentine" and the episode "Head Over Hogatha". "Chlorhydris' Lost Love" takes place on a similar day called Smurfy Friendship Day.
- Hey Arnold! had a Valentine's Day episode where Arnold had a scheduled date with his crush Ruth Mc Dougal and his French penpal Cecile (who was really Helga pretending to be Cecile). Luckily, both dates were at restaurants that were across the street from each other, allowing him to bounce back and forth between the two.
- The Backyardigans has a Valentine's Day episode call "Special Delivery".
- Wow! Wow! Wubbzy! has a few Valentine's Day episodes like "Mr. Valentine", "Cupid's :ittle Helper", and "My Speedy Valentine".
- The Berenstain Bears has a Valentine's Day special called "Comic Valentine".
- On the The Fairly Oddparents episode "Love Struck" Timmy tries to impress his crush, Trixie Tang, with a big fancy Valentine, only for her to turn him down yet again. Angered by this and the fact that Cupid claims his real Valentine is Tootie, he wishes away all the females in Dimmsdale, creating two different lands separating the genders by a wall.
- The Madagascar franchise has a direct-to-DVD Valentine's Day Special, entitled "Madly Madagascar". This special takes place in between the second and third films. Valentine's Day is revealed to be Alex's favorite holiday, Melman plans a surprise for Gloria, Marty tries to impress a new friend, and everyone wants to get their hands on King Julien's love potion.
- The Powerpuff Girls has the episode, "Keen on Keane", where the Girls set Professor Utonium and Miss Keane together with fake love letters. Soon, they fall in love with each other, and talk to each other through the hot line, tying it up, and thus The Mayor can't tell the Girls that Townsville is in trouble (because he thinks it would be rude to interrupt). When he inadvertently interrupts by sneezing, The Professor and Ms. Keane realize they've been neglecting their responsibilites, including Ms. Keane forgetting to feed her pet cat, Valentino. This causes the Professor to break up with her, as he had a bad experience with cats before, specifically an evil one that made him jump off a building.
- Camp Lazlo On "Valentine's Day", Patsy gives Lazlo a Valentine.
- In the Muppet Babies episode, "My Muppet Valentine", Nanny makes cookies for the babies. Unfortunately for Rowlf, he doesn't get one. His friends try to make it up to him by making him a surprise, but worry they've made him feel worse by leaving him out of their activities so as not to spoil the surprise. As it turns out, Rowlf has a surprise of his own for his friends; a song he wrote called, "You're Special to Me". At the end of the episode, Nanny finds Rowlf's cookie on the baking sheet and gives it to him, proving she thinks of all her children as her valentines.
- The Magic School Bus has the episode "Gets Charged" which takes place on Valentine's Day.
- The Adventures of Jimmy Neutron has the episode Love Potion 976/J which has Jimmy and his friends accidentally exposed to a potion that makes them fall in love with the first girl they see, and dealing with the side effects interfering with their own lives.
- The Animated Adaptation of Clifford the Big Red Dog has the episode "Cleo's Valentine Surprise". The spin-off series "Clifford's Puppy Days" has the episode "Valentine Shmalentine".
- The Animated Adaptation of Curious George has the episode "Happy Valentine's Day, George!'' all about George trying to make Valentine cards for all his friends before the end of the day.
- Episode 83 of Kaeloo is all about the characters going to a Valentine's Day party, where Mr. Cat makes Quack Quack break up with his girlfriend just so he can get Kaeloo to be his date at the party.
- Miraculous Ladybug has one, complete with a Cupid-themed akumatized villain and a Big Damn Kiss between our heroes (granted, it was only to snap Cat Noir out of the villain's Hate Plague, but still...).