Pre-notes:

I like the setting of Sun and Moon, and the fact that there are so few stories set in it made me very sad. Hence, this story was created.

Essentially it will be a story about Ash maturing and actually finding something greater than the two-dimensional characteristics the anime gives him. And surprise, everybody ages. In this case, the three main characters will be:

Ash ~ 16

Lillie ~ 15

Mallow ~ 16

Everybody else will be aged up relatively to them, so Brock would probably be in the 20s, Misty 17, etc.

As the tag suggests, this will be a romance and adventure fic. There will be battles, but since my goal is actually fleshing Ash out as a character, character interaction will take priority. What he will be doing on Alola will be revealed next chapter in writing, but he will be teaching at the Trainer School that Samson Oak is the principal of. In contrast to the anime, the trial captains are not students but volunteer teachers/tutors instead. For the next few months, they gather together at the school to improve themselves and help others as the trial season is temporarily over. We'll see tons of interaction here for Ash, some comedic, some dramatic, but I hope all meaningful in some way. In terms of plot, I will be combining elements of the game and the anime as I see fit, this is also true concerning the personality of some of the characters (I'm obviously already taking liberties by actually aging them). Pokémon wise, Ash will be catching a few new ones, but will primarily be concentrating on strengthening the bonds and power of his current team (Kalos and before), including actually evolving Gibble into Garchomp.

Ash has been asked some questions that shake some of his foundations and it acts as a catalyst to his growth. The reasoning may be slightly wonky because I didn't want to turn it into a betrayal fic or anything of the sort, but I hope it is sufficient (BASICALLY, ITS NOT A BETRAYAL FIC).

NOTE: For Oak's argument, if the Pokémon does not appear in battle on any episode, I say they didn't do battle.

Hope you enjoy.

Line break implies a time skip

0o0o0o0

Implies a scene change

Disclaimer: All I own is this story. Pokémon and its associated products belong to their respective owners.

_Prologue_

There had always been a special something in the night air around Pallet town. It was distinct, vaguely comforting for the raven-haired male who sat on the hill overlooking it.

Kanto.

Johto.

Hoenn.

Sinnoh.

Unova.

Kalos.

Six whole regions and everything in-between he had travelled through over the span of six years, yet somehow the smell would always come back to him. He had to admit that he found the feeling surprisingly comforting. After all, he loved to travel and was never able to stay still for long, but it nevertheless felt... nice to be home again.

…

The contrast was rather maddening.

He chuckled at the oddity of such a conclusion, and chuckled even harder at the fact that he was even partaking in the act of self-reflection.

He paused suddenly before collapsing onto the grass, releasing a tired sigh at the thought. As he looked to the stars above, his mind once more began to wander. Most people, if not all, would agree that he was far from the sharpest tool in the shed, and unfortunately, he also begrudgingly agreed with them. He was brash, impulsive, lacking in tact…

…

Perhaps if he had self-reflected more regularly, this wouldn't have been such an issue. And maybe then, he wouldn't be lounging alone on a nondescript hill in an attempt to escape his problems.

4 hours earlier…

"Ash?"

When he found himself before a certain section of his simple home, his eyes began to trail over the pieces that decorated it. A numerous number of trophies, badges, symbols and photos stood before him, returning his stare silently.

"ASH?"

As he steadily lost himself to the memories, a hotchpotch of conflicting emotions stirred within him, pride, joy, excitement, nostalgia, fear, and disappointment, all waging conflict within him.

"ASH KETCHUM! Can you please come down?"

Nearly tripping over the sudden intrusion to his thoughts, he found himself slipping. Deftly regaining his balance from a near fall, he shook his head once more to regain his senses.

The voice of one Delia Ketchum, his mother, had awoken him from a sudden stupor. Curious concerning the intent behind her actions, he quickly descended the stairs to find her. Yet, what he found was far from what he had expected.

Rather than a single brunette, he found himself surrounded by an amalgamation of familiar faces. All of whom sported an assortment of colors, both appearance-wise and personality-wise.

"SURPRISE!"

He could scarcely hide the smile that grew on his face at the sight. After all, good friends weren't always easy to come by.

"What are you all-"

Barely beginning his question, he felt the wind knocked out of him as a blue blur slammed into him. Feeling arms wrap tightly around him, he reflexively returned the gesture with a heartened grin.

"Dawn! I missed you too, but was that really necessary?"

She merely chuckled sheepishly in turn, "Whoops. Sorry, but it's so difficult to get a hold of you sometimes."

"Urghh… don't even get me started on that."

"I have to agree with her, Ash. It would be nice of you to call more often."

"Yup, if his idol called more often maybe Max wouldn't let everything get to his head so often. Drew's been somewhat of a bad influence on him lately."

He turned to face his accusers with a mock indignation, "Misty! Brock! May! It's good to see all of you. But c'mon, cut me some slack, please? I send letters don't I?"

"We have phones, Ash! PHONES! INSTANTENOUS COMMUNICATION."

"Misty please, not the mallet!"

He could hear his friends chuckling around him at his antics as he evaded the water-Pokémon lover. It was good to be around them again, always exciting but familiar at the same time.

0o0o0o0

"So, none of you ever answered my question. What are you guys doing here?"

It was Brock who answered him with a grin, "What? We can't congratulate a close friend for being a runner-up at the Lumiose Conference?" A round of ridiculous congratulations followed immediately after the man's statement, bringing a rather amused smile to his face.

"Although, your mom also called us in for something extra-"

"MISTY!" A yell interrupted her, silencing the room immediately with its intensity. He turned to locate its source, easily finding a brunette sporting a deep frown marring her expression.

"May?" He raised an eyebrow at her actions. They were odd, unnatural for the Hoenn-native coordinator. Yes, she had a temper, and Arceus knew how many times he had incited it, but rather than angry, she almost seemed pained.

"Sorry," she sighed, "but we'll explain soon." He merely nodded in reply, intrigued.

His attention, however, was immediately distracted as a yellow ball of fur deftly jumped onto his shoulder. Bringing a short round of chuckles among them as Pikachu also greeted his long-time friends with avid enthusiasm. It didn't take long for the mood to recover, as the others also released their smaller Pokémon, allowing them to interact freely among themselves. The trainers themselves steadily returned to their familiar show of friendly banter and good-natured ribbing. Stories were exchanged, smiles were shared, and high-fives were freely exchanged between them all, interrupted occasionally by the antics of some of their Pokémon. All in all, he had found it an excellent start to the evening.

In the midst of another story concerning Brock's quest for love, however, his mother returned through the door with another trio of familiar faces. All of whom, he had already seen just his morning.

"Gary? Professor Oak? Tracey?"

"Sup, Ashy-boy? Me, gramps and Tracey here got invited to your little shindig. Hope you don't mind some extra company," Gary asserted with his typical smirk.

Throwing a light glare at his grandson, the professor merely sighed exasperatedly, "Good evening, Ash. I hope you don't mind our little intrusion."

"Not at all, professor! The more the merrier, right?" He could hear some his mom chuckling knowingly at his response behind them. After all, she had raised him and probably knew him better than he did. However, the abruptness of her stopping immediately garnered his attention.

For one reason or another, his gut began to twist and turn,

"Alright everyone, before we begin… we all have something to talk about, Ash." His mom smiled kindly at him, and he naturally returned it. Yet, it was obviously tainted with something. The question was, why?

"Mom?" He asked hesitantly, "Is everything alright?"

Silence commanded the room for a moment, as only eyes moved hesitantly between them. He could feel the twisting in gut growing tighter as the silence lingered. His instincts screamed, but for the life of him, he could not say why.

His mom sought to begin, but faltered. She hesitated once more, turning instead to face the professor. The older man sighed tiredly and began, "Ash, what is your dream?"

He stared incredulously at the man, blinking owlishly in surprise, "Professor, you know what it is."

"Refresh my memory. Please."

"To become a Pokémon Master," he affirmed confidently, smiling as Pikachu nodded alongside him from his shoulder.

"And how have you been going about achieving this?"

"C'mon, you kno-"

"Ash," his mother interrupted him, "answer the question, please. For me?"

He paused and smiled hesitantly at her, "I've been travelling the regions and competing in the various leagues. That's how I've met the people around me and all of my Pokémon."

"Right," the professor sighed once more. "You've been doing well, Ash. Incredibly so, and the experiences you've lived through are numerous and extraordinary. If anything, I believe you've encountered more living legends in six years than most people ever will. But, what I'm trying to say is-"

"We think you should stop."

The mood soured quickly. Ash could feel his heart drop to his stomach at the words, his jaw clenching as an assortment of emotions rushed through him. Confusion came first as he sought to confirm what he had just heard, then sheer shock seemed to stop time for him, before finally anger began bubbling within him.

"What?" His voice was quiet, scarcely above a whisper. Nonetheless, it carried an edge.

"Damn it, Gary!" He could hear Misty yell out exasperatedly.

"Ash, let us explain," it was Brock who broke through to him, gently placing hands onto his shoulders. He could feel himself calming under the man's comforting grip, stilling the subconscious shaking that he had begun.

"Ash, we don't mean permanently," his mother's small voice penetrated through the small crowd. "Just give us a chance?"

He merely sighed in response, "Alright."

"Why do you do things the way you do them?"

He raised his eyebrow at the professor, rather baffled at his question. "What do you mean?"

"Let's start with a different question then… Why do you insist on going to almost every region with none of your older Pokémon?"

He paused for a moment before answering, "Because, I want to meet and train new ones?"

"A fair answer; but, why don't you bring them along and switch them gradually at the PCs? It's not as if centers are a rare sight in any region."

"They deserve a rest," he muttered. It was the best answer he could think of at the top of his head.

"For years?"

Ash could feel his fists clenching slightly as he spoke, "What do you mean?"

"When was the last time you battled with Bayleef? Or Totodile? Or Gible?"

He remained silent in response. In truth, he didn't really know. He saw them often enough at ranch attached to Oak's lab, brought them up sometimes at leagues just in case, but actually battled with them? It had been a while.

Taking Ash's silence as a cue to continue, Professor Oak spoke, "At least 3 years, most of them in Sinnoh. Are you giving up on them?"

Immediately, his anger returned in spades at the question. He would've never entertained such thought, let alone actually put it into practice. "NEVER! They're basica- no, they are family; and I would be willing to die for any them. You of all people should know me better than that."

"And they all adore you for that, most would probably return the favour and would also be willing to die for you; some would even be willing to kill themselves if you asked them to," the fact that Pikachu nodded affirmatively at the professor's statement was indeed comforting, but it did little to sooth Ash's nerves for the moment. "Nevertheless, tell me why?"

"I don't know…" He spoke through gritted teeth, nails digging into his palm as his fists tightened.

The professor released another sigh, pausing for a moment before frowning. "Why are you limiting yourself, Ash?"

"What. Are. You. Asking?"

"You've travelled through six different regions, gaining more experience than almost any other trainer your age. You are a good trainer, Ash. Nobody can deny that.

The champions of every region know of you. You've gained the respect of Lance, champion and G-man. Even Champion Cynthia could see something within you. You've gained entry into every league, passing the preliminaries of each one on your first try. You're a pseudo-champion after conquering the Orange League. You've bested the Hoenn Battle Frontier, a feat few can claim, and even fewer can claim that they were offered a place among them. You're the champion of countless number of tournaments across the regions. You've even been saviour of this planet, multiple times I might add.

So tell me, why is winning any of these leagues so difficult for you? It's obviously not your Pokémon, you absolutely adore them and they return the sentiment. So the question remains, why are you limiting yourself?"

A part of him wanted to lash out in response, to accuse all of them betraying his friendship. Yet, he found himself unable to do so as his fists slowly unclenched in exasperation. He could feel his hardier emotions gradually leaving his system, his anger dissipating first while the rest following closely.

He felt hollow.

"Ash," Professor Oak spoke softly, bridging the gap between as he placed his hand on Ash's shoulder. "You have the potential to not only be a good trainer, but an amazing one. The dream of Pokémon Master is not unreachable. It's just…" The professor sighed tiredly, rubbing the bridge of his nose as his frown deepened, "You have that special connection to your team, the experience, the instincts, the natural talent, the knowledge, and even the creativity to further distinguish yourself. After all, how many trainers can claim that they've even considered using contest moves to overcome an opponent in a straight-on battle? But nonetheless, you just don't have the wisdom to put them all together, at least not yet. I know you are aware of 'type-advantages', 'special abilities', 'hidden abilities', 'mega-evolutions', among other things, but you just aren't considering them enough. League matches come down to the wire, and you will need every advantage to succeed."

Ash remained silent in reply. Even if a large part of him wanted to deny the man's words, he was found himself begrudgingly agreeing with them. The professor was right on almost every count. Losing to Ritchie, Harrison, and Tyson in his first three years was acceptable; after all, he didn't have the experience he had now. Even losing to Tobias was forgivable, legendary Pokémon were dubbed thus for a reason. But losing to Cameron, losing to Alain, it couldn't be blamed on anything but his shortcomings.

He then turned to face the others and asked, "Do you all agree?"

They exchanged nervous glances between themselves, obviously unsure over what they were supposed to do, let alone say. Even Gary was being uncharacteristically sombre for a change. The sight would've brought out a chuckle out of Ash in any other situation. Unfortunately, it wouldn't tonight. Ultimately though, they agreed with the sentiment and replied with small nods.

"You've done so much for all of us, Ash. We know you can do this, and we all want you to succeed from the bottom of our hearts. But lately, whenever we see you, there's just something lacking… We don't know what it may be, but it's obvious that every Conference weighs on you," Brock spoke softly with a chagrined expression.

"Ash," his mom began meekly. He cringed inwardly at the sight, saddened at the thought that she could make such an expression on his behalf.

"Mom."

"Please understand. We're not betraying you or anything stupid like that. We all care for you, we all have the utmost faith in you, and all of us know you can achieve anything when you put your mind to it, but…" She paused, momentarily twiddling her thumbs in thought, "I've seen you get increasingly lost in your memories whenever you pass your accomplishments, and it worries me. Your eyes turn empty, you don't even notice when Pikachu leaves your shoulder to get me, and you've begun to stiffen slightly whenever a league is mentioned. Initially, I didn't think too much of it whenever you came home, but it's been getting worse every year. Arceus knows you would never blame any of your Pokémon for your shortcomings, so that leaves us with the world, the people around you, and yourself to blame. And I know you are much too kind to blame the former two."

He felt her arms slowly wrap around him as she finished, and his chest tightened as a feeling of dampness started to cling to his shoulder when she leaned on it. "Disappointment accumulates, and I just don't want to see you break, Ash."

He had returned his mom's hug and whispered out an apology to her, before apologising to the rest of them and excusing himself. They had begun to protest, but he left Pikachu with them as a sign that he would return, it just felt like he needed the time alone.

Ash released another sigh. They were right, on all points, and it worried him greatly that he was unable to see any of it. He'd been so eager in the pursuit of his dreams that he'd failed to take notice of the fact that he'd been narrowing his sights. Every region, he'd done essentially the same thing over and over again, almost never altering his methods, improving them, refining them, so obviously he would fail each time. He felt like a fool.

So now what? What exactly was he supposed to do? Should he travel with one of his friends again? He chuckled at the various possibilities that came to him, of him doing contests again with May or Dawn, of being buried under a pile of notes as Brock studied to become a Pokémon Doctor, or as Misty's whipping boy at the Cerulean Gym. He shuddered at the idea of the last one.

Yet, none of them really felt right. He had always travelled with someone, having people to rely on and be relied upon. Perhaps, he'd been using them as a crutch this whole time? He cringed, he sincerely hoped otherwise, but it seemed increasingly likely as he continued to ponder.

…

Should he find a remote mountain top and silently brood as he trained his Pokémon? That sounded absolutely ridiculous. Visit a region again? No, he would probably end up returning to his old habits again. For the first time in years, he felt that he had completely lost his way.

…

Perhaps the one who had answers was the one who started it all. Picking himself up, he began the trek home with a solemn smile.

0o0o0o0

Walking through the front door of his home once again, he sighed inwardly at the impending discussion before him. He had expected his mom alone to have remained awaiting his return, but life continued to surprise him as he found the professor drinking tea cross from her.

"Everyone's gone home?"

His voice immediately caught the attention of the two adults, and his mom was the first to move. Once more, she quickly bridged the gap between them and pulled him into a tight hug, mumbling apologies into his shoulder as she did so.

"I'm sorry, Ash. We hoped that with your friends here- I just-"

"No," he interrupted softly, returning the hug. "You were right." He paused to look at both of his primary authority figures. Both incredible people that he respected with all of his heart, and felt assured would work tirelessly for his good if needed. "What should I do?"

Heh. Perhaps he had matured somewhat if he was able to even understand that.

She separated herself from him, wiping small traces of tears from her eyes before turning to share a look with the professor. He nodded in reply and spoke, "I have a cousin, Samson…"

Shielding himself from the sun with the brim of his cap, he readjusted the duffel bag on his shoulder and exited the plane. The air was warm and humid, its effects lessened slightly by the occasional light breeze. Palm trees could be seen on the outskirts of the terminal and the beautiful blue ocean with it.

It was a tropical paradise by every sense of the word.

"Well, we're here Pikachu. Hello Alola."

Post-note: I'm busy, so updates will be sporadic. Leave reviews when possible please.