Pokemon First Date Headcanons

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.


Dawn and 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 didn’t.’


Cilan’s 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.


Clemont 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.

Pokemon Dancing Headcanons


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:

No comment. 


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.


Gold took him to Hot Topic and this was his reaction

And this was Gold’s reaction when Silver dressed up in some very questionable clothing there

Meanwhile Clemont is being harassed by Bonnie on getting a girlfriend, “What, do you not want a girlfriend?” Clemont isn’t sure how to tell her that he’s actually really gay for Ash but whatever

(I actually had a hard time choosing if I wanted to draw Clemont or Cheren because they’re both my favorite Gym Leaders but. In the end Clemont won lolol
I’ll definitely do Cheren next time, he’s my son <3)

Thanks for requesting these! Lol I’ve done so many now that there are repeats of certain expressions popping up but that’s okay! I’m not going to take any more requests though; I’m going to do the ones remaining in my inbox and when those are done…I’m going to do another meme similar to this one but with ships. So. Look out for that ^^

Pokemon High School Headcanons

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.