Ash and Misty’s first kiss was anything but serious, basically underage drinking happened and a very intense game of truth or dare. Most of their friends were around and also tipsy, and for some reason May, Dawn, and Iris got it into their heads that they should dare Ash to kiss Misty. The two comply, but in the most comical way possible, sucking on each others faces in the most unromantic way. This gets a lot of laughs from their audience and they say no more about it. A few weeks later Ash and Misty are swimming in the Cerulean City Gym’s pool and Ash casually brings up the occasion. Misty is mortified as she had little to no memory of that night due to her alcohol intake, so Ash teases her relentlessly about it, splashing water in her face and taunting her. Once Misty’s face was redder than a beet Ash asked her if he should remind her. This confused Misty since Ash was not in tune to romance or anything akin to it, before she could reply he gave her a proper first kiss, one that both of them would remember. They each tasted like chlorine and it was a little weird, but that didn’t mean they didn’t enjoy it, or do it again.
Drew recognized the fact that May was not the perceptive type when it came to love. He had been pretty damn obvious about it with the roses and everything so he decided to go for an even more direct approach. As had become their tradition over the years, whenever they met up while traveling they would go out for coffee or lunch (not dinner because Drew knew of May’s insane eating habits and did not want an empty wallet). One day while they’re both in the same town for a contest, after getting coffee Drew asks if she wants to take a walk around with him. May, bring May, accepts and is blissfully ignorant of his intentions. They’re walking through a park and out of nowhere Drew lifts her up off the ground, causing her to shriek, half out of surprise and half out of confusion. He then proceeds to press his lips against hers, May remains wide eyed and completely in shock. When he pulls away she demands to be let down, Drew smirks at her embarrassment and she orders him to never do that again. He agrees with mock sincerity and May storms off angry but sort of turned on. Needless to say he breaks his promise very quickly the next time they meet up.
In a moment of what Paul calls insanity, he sleeps with Dawn. It was a spur of the moment and heated decision, definitely would not be described as ‘making love’. They proceed to do it every so often, no strings or feelings attached to their midnight rendezvous. The only rule Dawn puts in place is that she doesn’t want him to kiss her on her lips as she finds the act to intimate for a noncommittal, purely physical relationship; Paul doesn’t really care and goes along with it. Everything was going fine until they started running into each other when they weren’t planning on having sex, in situations where they would actually have to converse with one another. Dawn soon finds herself attached, much to her dismay, and Paul now finds it awkward to sleep with someone he would consider a frequent acquaintance. Basically they both agree to call it off. They continue to run into each other, and during one of these times Dawn plucks the courage to talk to Paul about their former arrangement. He isn’t very communicative but Dawn persists, apologizing for the trouble it caused and making a sad attempt at explaining her reasoning. When she finally stops babbling the two look at each other and neither of them are sure who leans in first, but their lips slowly meet each other. Neither of them had a clue what they were doing so their lips didn’t move and their hands stayed by their side. When Paul pulled away Dawn hadn’t realized she’d closed her eyes. This begins a very tentative and careful relationship between the two of them.
Cilan knew of Iris’s crush on him, and Iris knew he knew and was pissed he did nothing about it. Never addressed it in the years they’d been friends and she’d liked him, not once. It was actually quite infuriating. In Cilan’s defense when he’d noticed Iris’s crush on him she had been twelve and he fifteen, hardly appropriate ages to act on such matters. Now with her eighteen and him twenty one he had no real reason to not mention it. Over the years they’d become best friends, they weren’t sure how it happened, but after she’d become a gym leader they found themselves always meeting up at events and the like. They’d talk on the phone often and send photos to each other. Over that time period Cilan had grown to care for Iris as more than a friend. She’d noticed it and it annoyed her to no end that he wouldn’t do anything about it, he was supposed to be confidant and outgoing and elaborately ask her out, but it never happened. Deciding to take matters into her own hands and took a plane to Striaton City, marched into the gym, and searched for her target. Cilan saw her and began to smile before he saw the pissed off look on her face. Cilan started to protest he hadn’t done anything but Iris cut him off wrapping her arms around his neck and kissing him. When she pulled away she chastised him for being such a kid and not having to balls to ask her out himself. On the spot he grows a pair and asks her to dinner. She accepts triumphantly.
Serena was susceptible to crushes, it was just the way she was. It never defined her existence or purpose but there was always someone that would come around and cause her heart to beat fast and her cheeks to flush. So once she had moved on from her infatuation with Ash, she was slightly surprised to find herself crushless. This went on for years as she furthered her career as a Pokemon Performer, it was strange but nice to not worry about impressing someone all the time. When she’s fifteen she has a performance in Luminose City, and simply has to meet up with Bonnie and Clemont before she leaves since they hadn’t seen each other in person for a few years. When she arrives at the gym a familiar feeling pierces her chest when she sees Clemont working on what she suspected was another one of his inventions, completely covered in grease, with messy hair, and his glasses falling of his face. She shakes it off quickly and greets the two siblings. After a few hours of hanging around in the gym and goofing off her’s suspicions are true, she has broken her streak of not having crushes. She eventually has to leave but before she does she makes a spur of the moment choice to have confidence in herself act on her infatuation instead of being silent like she had on every other occasion. Serena delivers her goodbyes to Bonnie and before Clemont can get a word out, she kisses him quickly and asks him to call her more often. He’s embarrassed and so is she. Neither of them know where it will go, but they take it slow and eventually one kiss leads to many more. Bonnie is thrilled.
Both of them are around six. Ash is sick in bed with a cold so they both are left to their own devices and one short one playmate. Gary and Leaf decide to explore Professor Oak’s backyard, aka the best playground ever for children who love Pokemon. As usual they get into an argument and without Ash to mediate their squabbles it makes it harder for the two to agree on things. When they reach the mutual understanding that wading in the river would be much more exciting than climbing trees for the umpteenth time, they finally have a mission. When they reach the calm river, sit on the side, and dip their toes in the cool water they notice the water Pokemon swimming about. The two spot a pair of Luvdisks kissing, and Leaf remarks on how she doesn’t understand why mommies and daddies do that sort of thing. Gary agrees with the sentiment, calling it gross but asks if she’d try with him as an experiment. Being the son of a scientist, naturally he’d want to test it to see if a reason could be found out. Leaf shrugs, not really caring either way, so they kiss each other, holding it for about five seconds before breaking apart in confusion. Leaf still doesn’t understand why mommies and daddies kiss and Gary has come to no conclusion other than kissing is overrated. Ten years later, that is not the case.
I’ve never posted headcanons before so these probably suck, but I’ve been slightly obsessed with these pairings as of late so I figured I’d post them
Ash and Misty hang out together all the time without putting the label ‘date’
on it. They go to movies, train together, and hang around the Cerulean pool,
that sort of thing. So it was hard to distinguish whether they were doing
things as friends or as more than friends because of that, along with Ash’s
lack of romantic knowledge. So when Ash finally mans up and realizes that he
wants to properly court his fair lady he asks his mum for advice. She suggests
that he should make a bold gesture something that sets the event apart from just
hanging out. So Ash asks Misty to join him for dinner at a fancy restaurant,
they both get dressed up, Misty wore a skirt and Ash didn’t wear a cap. Ash
gives her a pathetic excuse for a bouquet, but she loves them all the same. Pikachu
comes of course and they are all ill-behaved because those three have no idea
what is appropriate in public and have no sense of etiquette. They end up being
kicked out of the restaurant, much to their amusement. On the way home Ash
awkwardly tries to kiss her, it sort of works but it’s way weird. Misty laughs
boisterously and teases him for it with Pikachu but on the inside she was super
embarrassed. He walks her to her door and Misty pecks him on the cheek and says
they should do it again sometime. This left him red faced and dumbfounded on
her door step. And they did do it again sometime, many times actually.
Drew knew he liked May but she was a little dense in regards to his advances,
despite the fact that she liked him as well so their first date didn’t start
off as a date. Drew mentioned he and Solidad were going to go to a non-competitive
coordinators conference in Lilycove City where retired performers gave lectures
and demonstrations. Solidad had bailed last minutes however so naturally May
whined about how she didn’t have tickets. Needless to say she was ecstatic when
he offered to go with her. During the day of the conference the two of them
just really seemed to have a good time, it was somehow different than when they
usually spent time together. Halfway through while May was laughing over some
joke she made that was apparently hilarious. Drew looked at her and was like
'I’m going to kiss you’ and he did. May was shocked to say the least but after
she collected herself and had time to process what had happened side glanced at
him and asked, 'Was this your plan all along?' He denies this, but she
teases him about it none the less.
Paul wouldn’t even admit to themselves that they were attracted to each other.
They had sort of gotten into the habit of training together; the two of them recognized
each other as worthy opponents. It was sporadic and they only did it if they
met by chance during travels, since they had no means of communication. One day
after a battle as Dawn was packing her things up to head back out on the road
when Paul approached her and stared for a while. When she finally asked what he
wanted he held his hand out and said, ‘Phone.’ She handed him her phone, and he
punched his number in wordlessly and with an impassive expression. He then said
that they could schedule their next battle when they were in the same area and
she should use this number to do that, then Paul handed her back the phone and left silently. And
all Dawn could think was, ‘Wait were these dates?!” Later when they actually established
a relationship Dawn asks him about this and he was like, ‘Wtf of course they
were, did I not make that clear?’ And Dawn was like, ‘Uh no Paul, actually you
request for a date was more dramatic than most marriage proposals so naturally
their first date was quite the event. Cilan took Iris out on a night on the
town, complete with five star restaurants, the theatre, dancing, and too many
other events. Iris appreciates the effort and has a good time, but Cilan could
tell she was getting a little nervous and overwhelmed by the city. When he
asked her about it she told him that he had given her such a great time, and
she wanted to return the favour, but in her own style. Iris called out
Dragonite and had it fly up in the sky with the two of them on its back, and
the two flew over the city and watched the lights. Cilan was very apprehensive about
how safe it was at first but after seeing how excited Iris was as they soared
through the sky, he relaxed and was able to enjoy himself.
spent heaven knows how long, working up the courage to ask Serena out. So when
he finally does, he stutters awkwardly and isn’t really able to get his words
out correctly. Serena, being the sweetheart that she is, understands what he’s
trying to do and gracefully accepts before he can really ask her. Clemont tried
incorporating one of his machines into their date but when it malfunctioned, it
sort of ruined his entire plan. He was really upset until Serena offered to cook
dinner instead and watch films for the night. Bonnie joins so it’s not exactly
a cozy romantic date, but they have an awesome time. Before Serena leaves she pecks
Clemont on the cheek and he musters up enough nerve to ask her out again. She
agrees of course.
Gary, a fairly
well-known name in Pokemon Research was invited to a museum unveiling. He had a
plus one and before he even considered taking anyone Leaf was like, ‘Yeah I’m
going’. He didn’t even have time to protest. On the day of the black tie event
Leaf is a little social butterfly, interacting with all the other guests.
Everyone comments on how nice Gary Oak’s girlfriend is. When Gary mentions this
to her and she was like, ‘So?’. He points out that they weren’t dating, and she
smirks and asks him if it would really be so bad. On the way back to Pallet
Leaf announces that she’s going to be his plus one for all of his research
events. Gary doesn’t protest.
He’d have the potential to dance well, but he sort of just… goes insane. His energy gets the better of him and he ends up looking like an idiot.
She’s actually quite a good dancer, growing up with her sisters she learned quite young. She doesn’t take herself extremely seriously on the dance floor however and is either amazing or absolutely awful.
Everyone thinks he’s a bad dancer, that is until he sees a pretty girl on the dance floor and proves himself a very competent ballroom dancer. Needless to say he’s quite the charmer when he’s dancing.
No one really pays attention to his dancing skills, it’s hard to focus on that when every time he dances somehow at the very least his shirt comes off.
He shouldn’t dance. At all.
May and Dawn:
They are both surprisingly good dancers, no one believed them when they said they could because of May’s clumsy nature but she proves them wrong. They have good synchronization and flexibility, particularly when they dance together.
His dancing leaves much to be desired but everyone always finds him adorable… and they laugh behind his back about it.
A surprisingly good breakdancer… can’t be graceful while dancing to save his life, which is ironic considering his profession.
He doesn’t dance but… if he had to he’d do it with the straightest of faces and the baddest of attitudes.
Kenny and Barry:
Iris has really good rhythm, she’s no ballerina but she can dance hip hop like no one else. It’s really the only kind of dancing she can do… but she looks damn good doing it.
He does a mean classical dance and ballet, he has a lot of grace and is great when dancing with a partner.
Burgundy and Georgia:
The only time those two would embarrass themselves enough to dance… is when they are drunk.
Absolutely hopeless… just… no… everyone always experiences second hand embarrassment from his skills.
Serena took ballet from a young and is very talented in the sport. She’s very beautiful to watch when she’s dancing.
Like her brother, she has no dancing abilities. That doesn’t stop her from dancing or having the time of her life however.
“The dream filling her large head is to be a Dragon Master. With the expectations of the entire Dragon Village resting upon her shoulders, she, along with days of training, comes to the battlefield. The maiden who knows the hearts of dragons, Iris!“
I know there’s some awful fanfiction out there for Pokemon high school aus but I figured why not. I’m jumping on the bandwagon, if these are cheesy as hell… well what else would you expect from a high school au? Seriously, if anyone knows a decent one I could read, I would be amazed and eat that shit up fast.
Ash would be that kid who tried out for the soccer team but was instead put on as the water boy/bench warmer. Then he’d have that cliche chance to prove himself when a player is injured at a big game and he gets to play blows everyone away and all that. He’d also be insanely popular, lots of friends, no one really knows why but he just knows everyone.
Misty would be on the swim team but one year Ash taunts her saying she couldn’t play other sports so she kicks his ass in soccer and forces herself on the boys team. Basically she’s a terrifying entity and a fearful legend to opposing teams. She’s also be a crap student, particularly when in a class with Ash, those two can’t shut up.
Brock would be that one dude in the Home Economics and Parenting classes. He does this for two reasons, the first being that he actually enjoys those classes, the second being that it means he’s surrounded by women. He’d be the school flirt, no girl has been left untouched by his charms. Sadly they don’t often have the intended effect.
Tracey would be that art kid who everyone is a little creeped out by. He’s a nice guy but when he’s sketching people can’t help but feel like they’re being watched.
Gary would be that guy everyone wants to shag. There isn’t much question about it. He’s good at sports but his inner nerd loves Science too much to try out for any teams. Instead he just mixes compounds and looks sexy in a lab coat.
May would be that ditzy student who is surprisingly talented in music but didn’t realize it until someone pretty much smacked her in the face. I can see her doing a lot of musical theatre and playing instruments. She’d be the type to forget there was a performance and then show up and wing it, not really knowing what she was doing but still nailing it. Classic scatterbrain.
Max is in middle school. No high school for him. He’d totally be that kid you’d steal notes from though.
Drew does a lot of musical theater like May, often playing lead roles, he’s a pretty nice guy and known for his singing voice. The only person he treats like trash is May, but that’s mostly because he’s a dork and doesn’t know how to react to a pretty girl he likes :)
Harley is the senior that everyone knows that once he graduates he will become a gay porn star. A very fabulous one.
Dawn would have similar interests as May, dabbling in music and the arts. She’s very popular with the male population but no one can figure out if she doesn’t realize it or just doesn’t give a shit because she doesn’t pay any attention to dating. She’d be a cheerleader for the sole purpose of cheering on Ash and chewing out Paul for being an ass.
Paul is the soccer team captain, known for his harsh… leadership? He rarely responds to anyone and most people just leave him alone because of ridiculous rumors about him, such as the one about him murdering the captain of another team in cold blood. In reality he is just a socially awkward dork with a weird need to play soccer.
Iris would be that kid playing pranks everywhere, that kid who runs in the halls even when teachers tell her not to. She hold the unofficial title of School Acrobat because she can literally climb anything and you never know what exactly she’s doing. She calls everyone childish despite her own attitude.
Cilan would be the peanut butter to Iris’s jelly, he’s dramatic and makes a spectacle of everything. He’s does a lot of dance and drama due to his personality. He’s an overall much better behaved person compared to Iris.
Burgundy spreads malicious rumors about Cilan… constantly. That’s literally all people know her for… that and her twitter/facebook rants.
Georgia is at war with Iris. To others it’s just pranks but to her it’s life or death. Their rivalry matches that of Ash and Paul.
Trip is similar to Tracey. Kind of creepy. He takes pictures all the time and no one knows exactly what he’s photographing which scares people. He has a blog too.
Clemont is a Science Nerd and the hero of the robotics club. Despite his nerdiness he is secretly the object of many female’s affections because of how freaking precious he is, but he has no idea. He always goes to Ash’s soccer games even though he hates soccer, he’s just a nice guy like that.
Serena is a dancer and basically the most precious person in school, she’s super nice and is friends with everyone, obscure or popular. She is also on the cheer team since she’s good at dancing but her main reason for trying out was so she could watch Ash play. She has a not so secret crush on him that everyone recognizes… except Ash.
Bonnie is also still in Middle School, but she’d be the one swiping Max’s notes for sure.
Jessie is that teacher that everyone is terrified of. Everyone wonders if she has a side job as a dominatrix due to her appearance and behavior.
James is the teacher who no one can figure out. He’s super close with Jessie but no one can figure out if they’re shagging or if he’s gay. He also brings his cat to work a lot.
And there you have it, my not serious at all headcanons about Pokemon characters in high school. Sorry if these were awful, but they were fun to come up with.