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The Increasingly Unlikely Adventures of Ash Ketchum

Summary:

Or, 5 times Ash meet old friends from his past journeys, and 1 time where he didn’t

Notes:

(See the end of the work for notes.)

Chapter 1: The Champion of Sinnoh

Summary:

After Serena’s first contest loss, will this mysterious woman help lift her spirits?

Notes:

Inspired by various fics about Cynthia and Ash encountering each other in Alola. Enjoy!

(See the end of the chapter for more notes.)

Chapter Text

Serena was stuck. Her first contest hadn’t gone… exactly as she had planned. This wasn’t the end, far from it…. But it still hurt.

She didn’t know how long she’d been sitting at the Coumarine city park, but she thought it would be a good idea to sit a little longer. Her Pokédex buzzed. A message from Ash.

She wanted to read it, she really did, but she needed to be alone, at least for now.

”Pokebuck for your thoughts?” Someone next to her asked, jolting Serena from her depressive haze.

“H..huh?” Serena looked beside her, spotting a blonde woman, wearing a black fur coat. Her appearance was regal, showcasing that only the brave and the foolish were to trifle with her.

Serena felt like she knew the woman’s name, but it escaped her still.

The woman continued, “You’re much too young to be down in the dumps on such a nice day. Pokebuck for your thoughts?”

 

Serena sighed. Better to vent to someone who didn’t know her. Someone with an unbiased view of her. “I…I feel lost.”

The woman nodded, gesturing for Serena to continue.

So, she did, “I lost my first Pokémon showcase. My Fennekin tripped, and I made a fool of myself.”

The woman blinked, “That’s… that’s a tough break. I’m sorry to hear that.”

Serena nodded, “I wanted to… I don’t know, I wanted to show my friends that I could do it. That I could… succeed, I guess. On my own terms, you know?”

The woman nodded, “All too well. If I may, will your friends think lesser of you after this?”

”No!” Serena shouted in offense, “They would never… he would never…”

“He?” The woman looked on, curious.

Serena sputtered, cheeks turning a shade of crimson she was all too accustomed to, “…I wanted to impress him. Show him that I’m not the crybaby in the straw hat anymore. Maybe if I did that, he’ll….”

”Reciprocate your feelings?” The woman chuckled as Serena’s words grounded to a halt, “It’s ok, I’m not judging. If what you say is true, then I don’t think he sees you as a crybaby.”

”I know he doesn’t, but….”

”You still worry he does. I get it.” The woman nods.

Serena and the woman sit in silence for a moment, watching the breeze flutter through a nearby tree as fletchling rest on its branches.

”I want to start over,” Serena finally declared, “Wipe the slate clean and return as a new me, you know?”

The woman nods and smiles, “Then a new slate we shall make. Come on, I know a brilliant hair place around here.”

”Oh, I don’t mean to impose.” Serena stutters.

The woman laughs, “Nonsense, I’m invested now. It’s been forever since I’ve had a makeover with a friend.”

Serena smiled, standing up, “Lead the way.”


2 Days Later


“Alright Clemont, are you even trying? It’s obviously the one about your occult obsession.” Serena snorted. Currently, she sat surrounded by her best friends around a bonfire, absent about 3 pounds of hair. She felt lighter, both in body and in spirit, the makeover with the woman doing wonders for Serena’s confidence. The almost imperceptible blush in Ash’s face after Serena returned with her new look was just the cherry on top.

Currently, the 4 sat around a bonfire, playing 2 truths and a Lie. Apparently it was an Unovan game that Ash would play on his travels there. 

”Actually….” Bonnie grimaced.

Clemont smiled sheepishly, “That was a long time ago, but I could still find the books if I wanted to… probably.”

”Wait s you’re serious?!” Ash gasped.

”As Pikachu’s thunderbolt. No, the lie was about enjoying ‘Riolu Kid 2’. I’ve never actually seen any of those movies.” Clemont admitted, to which Ash further gasped.

”How  dare you. I’ll have you know Riolu Kid is possibly the greatest movie to ever exist.”

Serena giggled at her crush’s antics. “Sure Ash. Why don’t you go next then.”

”Fine. Let’s see….” Ash thought for a minute, before snapping his fingers, “Got it. I have died about 3 times during my journeys, I have champion Cynthia’s contact information, and I once caught 30 tauros in a single day.”

The three others just stared at Ash, unsure of what to even say. Surely he had to be cheating, but it wouldn’t make sense to lie about all of those things, right?

“Well… the Tauros seems to be the least far-fetched.” Clemont coughed, “Dying 3 times seems unlikely though… that just leaves having THE Cynthia’s phone number, which I doubt you have.”

Serena nodded, trying not to think of how Ash could have died, “I… don’t know on this one. I’m going with Cynthia’s contact info.”

Bonnie nodded in agreement, “Yeah, how would you know Cynthia anyways? Isn’t she a big-shot trainer?”

Ash smiled mischievously as he took out an old X-transceiver from his Unova days, clicking a few buttons, “One of the biggest.”

The X-transceiver ringed for a few moments, until the person on the other end picked up. It was a woman’s voice, young-ish, and very much still asleep. “Ash? It’s 2 in the morning, what do you want?”

Ash smiled sheepishly, “Oh, sorry Cynthia. Just needed to prove a point to some friends.”

”New friends already Ash? You must… yawn … be in a new region, right?”

”Yeah, Kalos. It’s a lovely place.”

Cynthia yawned again, “Ash, I’m in Kalos right now too. Why are you still up at 2 am?” 

“Wait, you’re in Kalos?! Man, we should meet up some time! You’d really like my friends…”

”I’m sure I will Ash…. But will you please let me sleep? We’ll meet in Coumarine City tomorrow, how about that?” Cynthia yawned.

Ash nodded, “Sounds good. Night Cynthia.”

The X-transceiver shut off, as Ash’s companions were flabbergasted.

”You…you actually know champion Cynthia…” Clemon stammered in shock.

”Personally, yes.”

”And we’re going to meet her tomorrow?” Serena asked, still not quite sure what just happened.

“Also yes.”

Serena, Clemont, and Bonnie just stared at him. How the hell was Ash this calm.

”Whelp, I should get to bed.” Ash suddenly stood up, Pikachu jumping into his shoulder, “Got a big day tomorrow. Good night!”

As Ash returned to his tent, none of his companions having enough coherent thoughts to respond.


The next morning Ash was almost literally jumping in anticipation. They had agreed to meet somewhere at a popular cafe in the city earlier that morning, to which Serena was more than pleased to hear.

She felt herself smile. Ash’s positivity and excitement were contagious, even without her massive crush. The fact that she was going to meet one of the most famous trainers in the world might also have something to do with it.

“Alright, this is the place!” Ash suddenly declared, as the four of them found themselves standing in front of a combined coffee shop and bakery.

”Sweet,” Bonnie said, “Where’s Cynthia? I wanna meet her.”

Ash looked around, just before a somewhat familiar voice startled them from behind.

”Right behind you.”

Bonnie yelped, quickly jumping to her brother’s side.

Behind the group was a tall blonde woman wearing a black coat. Serena did a double take.

”YOU?! YOU’RE CHAMPION CYNTHIA?!?” Serena couldn’t believe it.

Cynthia just took one look between Serena and Ash, before smiling to herself, “Ooooh, I get it now.”

”S..stop that!” Serena converted her increasingly red face with her hands.

Ash didn’t seem to notice, instead introducing Cynthia to Bonnie and Clemont.

”It’s an honor to meet you Ms. Cynthia. I’ve seen a few of your battles.” Clemont said as he shook Cynthia’s hand.

”You’re a gym leader, right Clemont?” She responded, “I’d be honored to see your facilities.”

”I’d be delighted, but I’m currently on break.” Clemont smiled nervously.

Cynthia nodded, “I understand. Journeying with this one,” she points a thumb at Ash, “is a once in-a-lifetime experience.”

Clemont laughed, “I’ve noticed. Just last night we were playing 2 truths and a lie. Ash’s we’re always so difficult because of all the places he’s been.”

Cynthia turned to Ash, “Is that why you called me at 2 am last night?”

Ash smiled, “Yup! Having your contact info was one of the truths.”

”Wait,” Bonnie asked, “What was the lie then?”

Ash shrugged, “I haven’t died 3 times.”

All but Cynthia sighed in relief. She braved herself for what was surely to come next.

“It was more like 5.”

Notes:

For those of you keeping track, the 5 times are….

- Got his soul ripped out by a Gengar in the Indigo League

- Got turned to stone after intercepting an attack from Mew and Mewtwo in Mewtwo Strikes Back

- Got devoured by an amoeba in Lucario and the Mystery of Mee

- Drowned in the sea temple during the Manaphy movie

- Froze in space during the Victini movie

Damn this kid’s been through a lot