With a Broken Heart

by Chibi Lovely

What if the kiss between Serena and Ash had happened on a different time and circumstances? And what if Misty had seen it? Causing her both, one of the biggest heartbreaks of her life but also the awakening of new powers and abilities that she'll need to navigate in order to go on and heal herself until the time her and Ash meet again. (Pokeshipping week 2024)

Intro:

What if the kiss between Serena and Ash had happened on a different time and circumstances? And what if Misty had seen it? Causing her both, one of the biggest heartbreaks of her life but also the awakening of new powers and abilities, including an unusual connection to music and Pokémon, that she'll need to navigate, and get help with from a different support network in order to go on and heal herself until the time her and Ash meet again. (A Pokeshipping story)

A story with inspired elements from different songs, and as I would have hoped the anime would have continued, acknowledging the passing of time and grow of their characters. Mainly pokeshipping, but other shippings will be present.

The main story will be at the point where Ash and Misty are both 20yo; however I needed to develop some of the changes in the characters, so the first part will be a prologue with the years leading to that point, especially from ages 15-20. Rated M for more mature situations later in the story, but especially the prologue could have easily been a T.

It is my first fanfic, so please be kind; I'd love to hear opinions and suggestions. Also, I'm not a native English speaker, even though I've been living in UK for a bit, there might still be the occasional error, even though I've tried to re-read extensively. Let me know if you find any error, and I'll get it revised J.

Disclaimer: I do not own Pokémon or any of the songs I've drawn inspiration from (I'll be referencing the songs if anyone is interested to listen to the original versions later on when they come up J). I only own the original story and characters in it (Not a lot of OC; as the series gave us so many memorable characters, I wanted to explore more those that in my opinion didn't get to show their full potential).

Prologue pt1. – Daisy's lullaby.

(Narrator's POV)

Years had passed since the time they travelled together, Misty had gone back to Cerulean Gym to take over as full time Gym Leader, which wasn't always easy, as she was always longing for the time she spent travelling with her best friends and having all sort of exciting adventures… well, the travels weren't the only thing she missed, but she's spent enough time trying to quiet down the inner voice that kept trying to remind her why she so desperately wanted to go back to those times, even if that was 10 years ago.

Now 20-year-old Misty was sitting on a plane, on the way to her next challenge, but in order to understand the events that led her to this moment, we need to go back a little bit in time.

She had no choice but to return to the gym 10 years ago, her sisters did not care enough for Pokémon battles to keep a good enough winning record to maintain the gym's license, they were always more passionate about having a career in show business, modelling… anything they considered more "glamorous", but Misty couldn't bear the thought of seeing her beloved gym being either closed or taken over by a complete stranger, and Arceus forbids, maybe even turned into a gym for other than water type Pokémon that she so much loved, so she had to do it, but there was always that annoying part of her that kept wishing to be travelling wherever Ash was.

She and Ash had kept in touch since last time they parted ways from their travels together. Up to when she was about 15 years old, there were a few gatherings which also included some of the other friends they all made along the way; Brock would come over whenever prep for medical school was allowing him to; May would visit when she had contests around. Well… Serena did too, but Misty had to admit, she was always more relaxed in the meetings where it was either May, Dawn, Iris… anyone else but Serena present; Is not that she disliked the girl, but her presence somehow always seemed to make Misty inexplicably sad and anxious.

The last gathering she saw Ash was when they were both around 15 in Cerulean, few things were happening about that time, and they somehow were all at a reasonable distance from her gym: Brock had just been accepted for Pokémon Med school at Viridian University, which brought quite a few of their common friends to come and celebrate him including Gary and Goh. There was also a big Pokémon contest in Saffron where Dawn, May and Serena were participating… May even ended up being the runner up in such a close result against another coordinator. Cerulean was hosting the annual gym leader forum where Cilan, Clemont, even Iris as former gym leader and Misty herself were all attending; and Ash was just back in Pallet from another of his trips.

With everyone in Kanto, they all decided to have a big reunion at the Cerulean Gym after the forum.

She had just turned 15, and that was not an easy age for Misty she'd probably have to admit, it was a time that now her sister Daisy kind of fondly remembers as "Misty's oversized hoodie era".

Up to that point, for some reason Misty was often described as a tomboy, which always confused her; yes she was hot headed and short tempered, but she also loved all sort of girly things like accessories, and like most girls she'd often be daydreaming romantic fantasies, but at 15 a lot changed, most of her girl friends had blossomed into beautiful young girls, and a few had even started dating. Dawn was the first to get a boyfriend, although that whole Paul episode seemed like a rollercoaster of emotions for everyone around; nonetheless, every other girl seemed happy and confident with their new self, while Misty had been content being the "late bloomer", still carefree and enjoying the same things she did while pre-teen.

But that summer it all caught up with her, almost immediately after turning 15, she was changing way more than she was comfortable or happy with, all the changes her friends were so excited and proud of, she just loathed the whole thing, it just didn't feel like she was herself anymore, so the easiest thing to do, was pretending everything was still the same, and try to hide as best as she could under oversized hoodies.

Anyway, that day of the forum and later meeting she did no different from what she was doing the rest of that summer, got on sporty lose clothes, put on the comfy hoodie and went on with her day.

The one thing she missed though around that time was swimming, ever since she started to change; she couldn't bring herself to wear a swimsuit (nor was she even fitting in any of her old ones).

Misty attended the forum and then went back to the gym to meet all her friends. Daisy, who surprisingly had gotten quite close to her youngest sister by that point, had offered to arrange the gym and get the snacks and preparations for the party (well, in reality it was more like she got Tracey to help set up everything, there was this on-going situation, where the gym suddenly had things "mysteriously breaking or missing" which always ended in Daisy asking Misty to call Tracey for help… Misty could tell the real reason why her sister would always come ask her to call Tracey, but she decided not to tease her sister about it, in fact; if a few weeks passed without the boy visiting and she noticed her sister on a down mood, Misty would go and break something herself, just to give him a reason to come and be around Daisy.

Misty always saw Tracey as the big Brother she never had (sure, it was similar to the bond she had with Brock, but somehow Brock was more like Ash's brother, while Tracey was hers), so the idea of him potentially becoming her actual brother was something that se really wanted to happen, and call it intuition or whatever you like, but something always told her those two would make a perfect match and she would proudly tell everyone that she was the one who made it happen for them.

Even though her sisters would often get on her nerves, she still loved them very much, and if she had to pick a favourite, that for sure would be Daisy. The 4 sisters had gone through a lot losing their parents very young (out of the 4, Misty is the only one that does not remember directly the face of either of their parents or any interaction with them), Misty was only 3 when she and her sisters were all left in charge of their grandma who did a wonderful job while she was around, but sadly she got ill, and when Misty was 9, they lost her too.

During grandma's sickness though, as she was so worried of what would be of her beloved granddaughters all alone in the world, grandma arranged for Daisy (Who was only 15 at the time) to be emancipated and legally considered an adult, and then have the custody of the remaining sisters (whose ages were 14, 12 and 9) go to Daisy, so at least they could all stay together. In a weird way, Daisy was more often than not, the closest to a mother figure Misty had, and as Misty grew older, she found even more love and respect for her eldest sister, that despite her shallow exterior, made the enormous sacrifice to basically end her childhood early to become guardian of her youngest sisters when nobody else could.

Even the whole "Fabulous sisters show" which initially Misty thought of as a "silly hobby of her sisters", was how Daisy managed to secure an income to the household and keep social services from questioning not only her ability to be a self sufficient adult with a stable job, but also one responsible for three other minors, so Misty would always wish nothing less than the best for Daisy, and would secretly consider her as her favourite sister, and they had grown quite close to each other; Daisy was often the first one helping Misty at the gym, like on that day when she volunteered to get the party ready (when conveniently Lily and Violet mentioned having a photo shoot in Cinnabar Island… Truth be told, they just did not like to hang out around younger teens).

When Misty came back with Cilan, Iris and Clemont from the forum, Daisy and Tracey had gotten the gym ready, and all the other guests had already arrived. There were many snacks and soft drinks (Even for the Pokémon), they set the music system (and Max somehow ended volunteering to DJ for the day) , and everyone seemed to be having a good time. As Misty arrived, she thought she was about to have the best summer day, but unexpectedly ended up being the most painful, at least since she lost her grandma at 9 (As she could not remember a single detail from the day she and her sisters lost their parents, so grandma's death was the first heart-breaking event that she remembers).

The party had actually started quite well, they were all hearing about the contest where May nearly got the title, but in fairness Dawn and Serena also did very well. Everyone also kept cheering on Brock for his entrance exam, and at some point later in the evening Misty managed to get some time with Ash to hear about his latest journeys and the Pokémon he caught along the way, and he was precisely talking about the new Floatzel he caught, which he insisted was the fastest swimmer Pokémon he'd ever seen, so Misty decided to test it out and challenged him to a swimming race in the outside pool against her fastest Pokémon then which was her newly evolved Clawitzer, the same Clauncher she'd challenged Ash for years ago last time they had the chance to travel together.

What Misty did not see, was that while she went to the back of the gym to get Clawitzer's pokeball, Serena had followed Ash to the outside pool, and by the time Misty got near the pool with her pokeballs in the bag ready for the challenge she was left frozen with the scene she witnessed, she was still some distance away from the pool but she could clearly see Serena leaning towards Ash kissing him tenderly.

Misty couldn't bring herself to stay there, and had the urge to run away, as she couldn't help but starting to cry, that was probably the last scene she would ever hope seeing that day, and effectively became the second heartbreak in young Misty's life.

Besides all the heart-breaking feelings, something really weird was happening, she started hearing all sorts of sounds almost exploding in her head, mixed with what it seemed to be as if at least 10 bands were all loudly playing completely different songs and clashing with each other, it was causing her the most horrible of headaches, and she didn't know how to make it stop.

As if the heartbreak and the loud sounds weren't enough, on her mind all sorts of outcomes from what she just witnessed were showing up. Scenarios like "They have been together for a while and this is just their normal" or "She took the first step and is the start of something unbreakable", "she took the first step but is not mutual", "He was actually the one pursuing for her to do that"…. Misty couldn't tell how many possibilities she was contemplating, but it was certainly more than she would have ever been able to imagine if she was consciously trying to write a list of "What if I suddenly walk into Serena kissing Ash?".

She didn't notice she was not running away through the same path she came in, instead she ended up heading towards the Garden, where Daisy and Tracey were just behind some of the rose bushes. At the time she didn't notice it, but she kind of interrupted her sister's make out session, although both Daisy and Tracey just became really concerned for the younger girl rather than upset; Daisy rushed behind her sister, and as Tracey headed towards where Misty came from to understand the situation, he noticed the 2 people on the poolside, and immediately caught on what must have happened for Misty to have reacted that way.

"Oh no" was the only thing Tracey could say in a very sad and concerned tone, before rushing towards the direction Misty and Daisy went. He was the only person that knew Misty's secret, at least the only one to get an admission from the girl herself about it. It was something he always sensed since he met the duo at the Orange Islands, but the fact Misty had finally admitted it to him while he caught her watching one of Ash's battles in a tournament on the TV, must have meant that the load the young girl was carrying inside her was so big, she no longer could bear it alone.

He tried to encourage her since to tell Ash about her feelings, but she always brushed him off saying "he's not that type of guy, he only thinks of Pokémon, is not ready for that kind of conversation, and I'm not even sure he'll ever be". Tracey did agree that Misty's point made sense then, considering how clueless and immature Ash still was, but Tracey always hoped they'd get together eventually.

By the time Tracey caught up with Misty and Daisy, Misty had just gotten herself inside the small Garden shed where the sisters kept all the gardening tools, she couldn't manage to lock herself in though, as Daisy got to the door just in time, and they were both in a struggle for it, with Misty trying to close the door, while her sister was trying to open it. He quickly approached Daisy.

- "Misty let me in! What's happening to you? – Daisy shouted.

- "Leave me alone!" – Was the only thing Misty said.

- "Did you get to see what must have made her react this way?" Daisy said in a lower voice to Tracey.

- "The thing is… I only saw Ash and Serena talking by the poolside, but" (Tracey stopped himself there, he had promised Misty never to reveal her secret, and he always keeps his promises, although he couldn't help revealing the concern and sadness of his voice as he said that answer to Daisy.

- "What? Oh no this is bad! No wonder she's acting this way" - Daisy said in the same concerned and sad tone.

As Daisy said that phrase, it took her and Tracey a couple of seconds until both looked at each other in surprise and exclaimed loudly, "Wait…. DID YOU KNOW?".

Daisy was the first to reply (While still struggling with the door)– " Of course I know! I can always tell what happens to my baby sister…. Even if she doesn't tell me herself WHAT… IS … GOING… ON!", she said this last part slightly angry and shouting for her sister to hear while still pushing the door with each of her last words, and said it all very confidently, almost like a mom who always knew what her kid was thinking.

Tracey just shook his head, he had to admit, around that time he already thought everything Daisy did was amazing because he was so smitten, but seeing this other side of her that actually knew and fiercely cared for her little sister more than Misty would always think any of her sisters would, actually made him feel particularly lucky to have finally gotten the courage weeks ago to ask the eldest Waterflower sister out, but he recognised this was certainly not the time for those thoughts so he went for the door to help Daisy get in to the shed.

When Tracey and Daisy managed to overpower Misty's efforts for the door, and finally joined Misty inside the shed, Misty just let herself fall and sat in the floor in defeat crying and holding her head in what looked like an attempt to calm a horrible headache.

- "I SAID LEAVE ME ALONE!" - Misty shouted while getting her own hands away from her head in frustration towards them, but as she did that gesture with her hands, suddenly everything that was sitting on the shelves on both walls around Daisy and Tracey fell to the ground as it "tossed all at once".

- "How did you do that?" asked Tracey genuinely in shock

Misty, by now terrified, as she also did not understand what had just happened, was still sitting on the floor and just moved her hands back barely replying "I… I don't know" but all the noise in her head was still there, maybe even getting louder and louder.

Daisy tried to approach her, but as she did, Misty got nervous asking her not to and moving her hands towards her, but even though Misty's hands did not actually reach Daisy, the eldest sister still felt a force pushing her, not massively strong, but certainly enough for her to feel it, and as that happened, the tools and items in the floor all started to shake slightly.

- "OK you definitely did something there, How are you doing it?", asked the eldest sister, but as Daisy saw Misty's terrified look clearly showing that the young girl couldn't understand either, and possibly was thinking that she might have hurt Daisy on that last "push", Daisy tried to lift the mood by saying "I'm asking because I'm…. kind of impressed, but I'm OK…. Are you OK?".

Daisy's earnest efforts got to Misty and managed to calm her down a little bit. As this happened, there was a flash coming out of Misty's bag, and this time it was… Psyduck, the usually clumsy Pokémon just approached his trainer and sat himself on his master's lap while hugging her.

She was confused as of why, but the moment Psyduck hugged her, she could feel as if a wave was helping relieve just a little bit the headache that by now she felt was going to crack her head in two.

- "Is this how you feel most of the time with your headaches?" Misty asked her loyal Pokémon. Psyduck said "Psy, psy, psy… duck" gave her a sweet smile and his usual head tilt which his trainer understood to perfection the reply as "a little bit, but it'll all be OK".

Misty was always losing her patience with her Psyduck, and it was rare that she understood his language so well; so all things considered… at least that gave her a little happiness.

As that thought was going through her head, a second flash came out of her bag, although this time it was….. Starmie? This made no sense to Misty, Psyduck was the only "rebel" of her Pokémon who would come out uncalled, Starmie never did that, but in a similar manner to what Psyduck did, Starmie approached her and leaned against her, and as the Pokémon did that, Misty felt another wave of relief making the headache level at least bearable.

Daisy and Tracey, who were very confused to say the least by that point managed to get closer to the girl and sat in the floor next to her and her Pokémon. Daisy was the first one to reach for one of Misty's hands, and as she did, again something really weird was happening on Misty's head; that loud music from seemingly over 10 bands clashing with each other started to quiet down a little, she could still hear them but it was getting quieter, and instead of that sound, she started to hear as if coming from Daisy a different melody, it was sweet and calming, almost like… a lullaby? It was for sure weird, but somehow Daisy's "lullaby" was much better to hear than all the previous "Clash of the bands" that was in her head.

Feeling as if all strength had left her body, Misty just stood there, as the tears went running down her face. Daisy took the chance and held her sister on a hug from the opposite side where Psyduck and Starmie were hugging her, until Tracey broke the silence.

- "It was quite impressive what you just did… almost as if you were moving everything around here without touching it. Has that happened to you before?" Tracey asked.

- "Not really" Misty replied, still crying and emotionally hurt, but a little bit more in control of her emotions as the lullaby from Daisy was still overpowering all the other disturbing sounds in her head. Daisy was not letting go of her sister, it was unusual to see the girl in such a protective stand of her youngest sibling, but Misty was grateful for her sister's presence at that moment.

- "It looked like Psyduck and Starmie knew what to do though, they must sense something we can't" – Tracey remarked trying to convey a calm and supportive tone while also complimenting the obvious empathy from the two loyal Pokémon. He was after all, very knowledgeable in Pokémon abilities even before joining Professor Oak at his Lab, and he's only gained more knowledge since working there.

- "This is the first time Starmie comes out uncalled" Misty said in surprise and genuinely confused.

- "Were Psyduck and Starmie the only Pokémon you had with you in the bag?" Tracey asked.

- "No, I have 6 pokeballs with me…. Gyarados, Clawitzer, Luvdisk and Corsola are here too" Misty replied trying to make sense of that just happened.

- "It certainly is an unusual duo to team up by themselves" Daisy said looking at the two Pokémon, now a bit more at ease seeing that at least her sister was engaging in conversation.

- "That's true, I do wonder why were precisely those 2 that came up, there must be a connection" Tracey said as if trying to solve a riddle.

Now, if there is something Misty was always very… very good at, was solving riddles. Ash and Brock knew this well when they all visited Cinnabar Island and it was Misty that solved all the riddles Blaine put their way until revealing his identity to the group. It was something that came to her naturally, maybe was partly due to her stubborn and fiery nature to not let anything get in her way to come with the answer for problems she wanted solved, maybe her brain was just wired differently, but whatever the reason was, she'd always focus all her efforts in getting the riddle sorted, no matter what, and she'd aim to do it before anyone else. The girl does after all, have a very competitive nature.

- "They can both use psychic type attacks" – Misty was quick to say despite still being crying, hurt and in shock. When both Pokémon approached her moments ago, the "Wave of relief" she felt somehow reminded her of the psychic type attacks both those Pokémon were proficient at, and it was the most obvious link she could think of.

- "That is true, it could be that those tools moved due to some sort of Telekinesis, although everything moved before the Pokémon came out" Tracey agreed curiously

Despite Psyduck not officially being recognised by Pokémon researchers as a Psychic Pokémon (Something Tracey did not particularly agree), the creature does display incredible abilities when his headache levels are high enough, and Tracey always had the feeling that Misty's Psyduck was a bit of a special case, he'd take much higher levels of headache to bring up his powers, but when he did, it certainly looked more powerful than other regular Psyducks he'd seen in action. Starmie on the other hand is indeed a dual Water-Psychic Pokémon, and in the past 5 years of training with Misty, the Pokémon had learned quite a few psychic attacks, which had helped Misty level up amongst the Gym rankings in Kanto. She had trained all her Pokémon really hard and they were all getting stronger, but Starmie in particular was one of her most reliable ones; however when everything in the shed moved, the Pokémon had not come out yet.

- "You mean telekinesis like those people on TV who move things with their mind?" Daisy asked, she'd seen stories on TV but never really met someone human, not a Pokémon, with such abilities in person.

- "I actually knew someone years ago who does that… well… much better than those posers on TV for sure, she moved things without touching them, teleported and even turned us into miniature rag dolls"

Misty said this as she was reminiscing her first visit to Saffron, but looking at the slightly terrified look on Daisy's eyes after the whole "turned us into rag dolls" bit she added – "She's cool now though, quite a good trainer, she's the leader in Saffron, I keep hearing she always holds one of the top 3 positions for Gyms in the region, I see her sometimes in gym conventions, although we never get a chance to talk much, always seem to be put in different tables".

Misty was still suffering inside, but the whole psychic connection and trying to solve the riddle of what happened was at least giving her brain something to focus on instead.

- " OK, we'll arrange a visit to Saffron then, maybe she can tell us if there's something happening with your Pokémon… or with you" Daisy added, a bit afraid to say the last part, but the force she felt pushing her seemed to have come from Misty rather than from any Pokémon.

- "Yes, that could be a good idea, I heard she trains a few students, she's supposed to be a prodigy on telekinetic abilities, we'll give her a call and see if we can visit her soon" Tracey added

- "But more importantly" – Tracey continued, "How are you feeling? Do you want to talk about what happened by the pool?" – He asked in his usual tone that always gave her the feeling she was talking to her older brother.

- "Yes, How can we help?" Added Daisy, now losing the hug with her sister and looking her in the eyes, desperately trying to convey to her sister that she knew her secret, but that she also like Tracey, was on her side.

Misty gave up on that moment all efforts to hide that secret anymore. It was now obvious to her that her sister knew enough, and Tracey did know as well, so she just finally let go and with even more tears coming from her eyes, while trying to cover her face with her hands she finally said what took her to that state.

- "I saw Serena and Ash kissing by the pool, I'm such an idiot. How did I not see that coming?" - Misty said in a defeated manner, something that was very unusual for the girl, she had always been the most competitive out of the 4 sisters, out of most groups of people her friends would even say teasing her, she always had a very strong fighting spirit with her, so seeing her like that was breaking both Daisy's and Tracey's hearts.

- "When I saw them they were only talking" Tracey was quick to add.

- "Do you think they saw me?" Misty asked in panic.

- "I really don't think so" The boy replied.

- " I cant go back and face them or anyone else today" The young redhead said, the last thing she wanted was for Ash or Serena to see how their "affair" was affecting her.

- "I'll go check on everyone and say you suddenly got a headache and fell injuring your knee, don't worry, you don't need to see anyone if you don't want to" – Daisy said, to which Misty replied with a very heartfelt "thank you", while still a little shocked that her sister was being so protective and intuitive.

- "I'll stay with her don't worry" Tracey said to the blond girl, while helping Misty up from the floor.

Daisy also was getting up herself and heading towards the party, but just before leaving the shed she turned back to face her sister and again looked her straight in the eyes while also grabbing Misty by the shoulders.

- "She's got NOTHING on you… you hear me? You are a Waterflower, and as such YOU… ARE … SENSATIONAL, don't you forget that!" - Daisy said loudly, with more conviction and fire Misty had ever seen in her sister's eyes, but before Misty replied anything, Daisy was already heading towards the party quite fiercely. It seems the hot temper is not something only the youngest sister inherited in the family.

- "She figured it out on her own, I swear" - Tracey was quick to add.

- "I didn't think she cared about me at all" - Misty said recognising now her obvious error. She could tell it was indeed Daisy figuring it out on her own, and Misty knew Tracey well enough to know he would never reveal her secret.

- "There is more to her than you give her credit for" - Tracey replied.

OK there it goes the first episode of the prologue. Initially I wanted to jump quicker to age 20 for Misty, but I then got really into writing more and more of the details on how I imagine her getting to that point.

As you probably noticed, Misty will be the main character here. I could never forgive the Pokémon Anime writers for focusing more on the goals of every single other "poke-girl" but Misty, when she was clearly the more interesting character, and in my opinion the one with more potential, so I wanted to show her becoming a badass on her own right first before the shipping actually materialises.

One thing I wanted to focus on was exploring the relationship with her sisters, these are basically 4 girls that were left on their own from a young age, it would be really sad to always have the relationship between Misty and the sisters be as bitter as it was in most of the show, so I wanted to give more depth to each of the sisters. Daisy being the favourite obviously, but you'll get to see from the other 2 as well.

Oh I almost forget, the title is inspired on the Taylor Swift song. I can totally see Misty becoming a badass despite having a broken heart, so it was a natural fit.

I'd love to hear opinions, there's gotta be more Pokeshippers out there J.