a/n: Writing angst and some edge. Buyer beware. This isn't a betrayal or anything fwi, Ash does something totally awful, and he deserves the backlash.

This story is gonna get super intense super quickly. Do not stay if you are expecting something sweet.

Apologies in advance to everyone who I offend.

-Cow/Blackfish

Oh! Ages!

OS took two years- Ash = 12

AG was two, Ash =14

1 for DP, Ash = 15

1 for BW, Ash = 16

1 for XY, Ash =17

1 for SM, Ash = 18

JN is six months in; Ash is 18 and a half

Chapter 1:

Few things are as special as a good friendship between two people. It's part of human nature to form bonds and connections with those around us, and in one trainer's case, he was an expert in the subject matter.

Ash Ketchum had a wide variety of friends, from coordinators to performers and inventors, and gym leaders. He befriended a wide variety of people. Nearly everyone that he met influenced him in some way.

Be it the strategies he schemed up with Dawn or the experience and wisdom he gained from Brock, and Ash received help from many of his friends.

Ash also helped some of his friends along the way, be it helping Serena and May to find their footing in the world of pokemon, encouraging Goh to open up and befriend more people, or simply sharing his positive attitude with others. Ash was a beloved friend to many.

However, there is a saying. "It takes years to build trust and relationships and one moment to destroy them."

This is a story where that saying will apply.

—-

The wind was freezing. Not like Ash expected a place called the "Crown Tundra" to be warm or whatever, but it was still absurdly cold. He had visited Snowbelle City and Snowpoint City in the past. However, this was a level above. The air was thin from the elevation, the wind was moving fast, and the snow was blowing into his eyes.

Despite all of that, Ash was in an incredible mood.

Not only was he recently promoted to the Master 8 tournament, but he also reunited with his old friend Lillie. She had finally reached her goal of reuniting with her dad, and after an emotional few hours, the newly reunited family left and decided to head home to Alola.

Ash, being the Alola region champion, decided to tag along. Goh and Chloe also joined in, wanting to see Alola again and for the first time, respectively.

It was a decently long walk back to the boat, but Ash was enjoying catching up with Lillie.

"So, Lillie, where exactly have you guys visited on your search?" Ash asked

"Oh, not as crazy as you'd have expected, just some islands around Unova called the Declore Islands, and then some islands around the Kanto region called the Orange and Sevii islands, and then we went to some islands around Hoenn called mirage isles,"

"I've been to the Declore and Orange Islands but haven't heard about any supposed mirage isles."

"Well, we lost our boat once, but that was because Gladion forgot to lay an anchor," Lilie laughed, remembering how angry her mother was

Ash smiled; it was great to see Lillie this happy.

She was always one of the people who Ash had fond memories of helping. She had such amazing growth as a trainer while he was in Alola; she went from being utterly afraid of touching pokemon to giving her brother a somewhat decent battle in the league.

Ash was proud of her, and while he wouldn't admit this to anyone, he was somewhat sad he didn't get to see her while he was in Alola earlier this year.

She always was the girl to who he felt like he had the best time talking to.

While his other companions could always make him happy, when he talked with Lillie, he always felt like he was smiling.

And sometimes, for whatever reason, he could feel the tinges of his cheeks warming up whenever she laughed.

"So Ash, I hear you're in the Master's Eight now!" Lillie said excitedly

Ash's face lit up, happy his friend was keeping up with his progress towards his current goal.

"Yeah!" Ash exclaimed, proud of his progress

"Wait a second, how did you find out? I never mentioned that to you or Gladion," Ash said, curious how she discovered this info.

Lillie laughed, "Ash, you're famous. Your battles are always on TV; Gladion and I watched you battle Drasna from Kalos! I will say, something must be messed up with that broadcast because the camera quality of the battle was abhorrent,"

Ash shrugged, "Can't say I watched it on TV, so I'll take your word for it,"

"Did you see my battle against Raihan?" Ash asked

Lillie nodded, "Yeah! I was on the edge of my seat the entire time! You really battled as a champion would!"

Lillie's praise made Ash beam, and he had been flooded with compliments after beating Raihan (and several death threats from his fans)

But for some reason, her praise meant more to him.

Ash smiled, "Well, I try my best. It's thanks to my friends like you that I have made it this far,"

Lillie laughed, "Do you even know that Alola practically shuts down when you battle? Shops close, and schools cancel lessons to watch it. People flood stadiums and town squares, cheering your name. They've seen what you've done for Alola on a world stage! You have caused the region to boom with tourists and new trainers taking on the island challenge,"

Ash stood dumbfounded; while he adopted Alola as his second home, he never assumed Alola would give him that incredible treatment.

Ash laughed, "Well, I'm happy to hear that. Oh, wait, Lillie, look! I see a boat! Is that the one you've been traveling on these past few months?"

Lillie nodded, "Yeah!"

"Think it can fit us?"

Lillie started laughing, "Oh, Ash, of course, it can. This ship is a converted Kantonian Naval Destroyer, able to comfortably house three hundred men. It's being operated by two psychic-type pokemon and an old sea hand. There's plenty of room, and frankly, I'd appreciate the company; it does sometimes get a bit lonely,"

Lillie's Vulpix complained.

"Nothing wrong with you snowy, but some new humans around is nice also,"

Snowy found that answer acceptable and continued trotting alongside Lillie.

Lillie laughed, "She's such a sweetheart,"

Ash, appreciating the interaction between pokemon and trainer, spoke up, "You know, Lillie, you've really come a long way as a trainer. I'm proud of you,"

Lillie's cheeks flushed red, but Ash couldn't tell if that was from the powerful gust of wind or perhaps something else.

"Well…. where'd that come from?" Lillie asked, just before the ship honked its loud and powerful horn, startling both Ash and Lillie.

The ship's gangplank immediately rolled down, and a door opened on the port side of the ship.

"Looks like we're being invited onboard! Let's hurry before it gets too cold below decks," Lillie said

The two trainers ran aboard, with the others following suit close behind.

After a few moments, when everyone boarded, the door closed firmly behind them.

The first thing Ash noticed was how warm it was below decks.

It was like a nice furnace compared to the bone-chilling cold outside.

Lusamine looked around before giving a demand, "Set a course straight for Alola! We're going home!"

Everyone cheered, and the ship immediately began moving. Supposedly, whoever was piloting the ship had very good hearing.

Lusamine and Mohn excused themselves, leaving the kids alone.

"I'm gonna go look for some warm tea. Does anyone want to join me? Chloe? Ash?"

"I'm good," Ash said, not liking tea very much.

"Same here," Lillie said

"Sure, count me in," Chloe stated

Gladion shrugged, "Here, let me show you the kitchen,"

Ash smiled and looked at Lillie. But, her eyes were gazed at the wall, her attention seemingly elsewhere.

Lillie was thinking about her last goodbye with Ash; she was…..she was so tantalizingly close to saying it. But she didn't, she couldn't. She hesitated one moment too soon, and Gladion had interrupted her. She was going to confess to him, but she was a coward, and right when she hesitated, the moment was gone forever.

She sighed and snapped back to reality. Ash was right in front of her, and despite trying to tell herself otherwise, she never really lost those feelings that she had for him. Even after six months of no contact, her crush never went away.

Ash looked at her puzzled, "Hey Lillie, everything alright?"

Lillie tried to snap back to attention, "Hmmm, oh yeah. Just a big day, reuniting with my dad and all,"

Ash sighed, "You know, seeing you reunite with your dad makes me happy. Makes me wonder that maybe one day I'll meet my own dad,"

Lillie smiled at Ash, "Well, who knows. Maybe you're closer than you think,"

Ash shrugged, "I mean, considering what you said earlier about me being famous, you'd have thought he'd have revealed himself by now,"

Lillie sighed, "Well, maybe he lives under a rock. Doesn't really care about pokemon battles,"

Ash looked hurt by the possibility that his dad didn't care at all for battles.

Lillie noticed this and instantly went to go and comfort Ash, "Oh, oh no, I'm so sorry, Ash, I didn't mean it like that, your dad will certainly support you no matter what, and even if he doesn't, you always have us. Your friends will always support you,"

Ash nodded, "Thanks Lillie, I really appreciate it. It's….kinda a tough subject for me if you can't tell,"

Lillie sighed, "I mean, up until a few hours ago, I could really relate. It hasn't been an easy journey for sure. I won't lie to you; there were several days that this whole adventure felt pointless, like we were searching for either a dead man or a man who had no interest in being found,"

Ash nodded, "Yeah….sometimes I wonder if that's the case for my dad, all my mom ever told me was that he was a good trainer,"

Lillie smiled, "Well, if he's anything remotely like you, Ash, I'm sure he's wonderful,"

Ash nervously scratched his hair, "Thanks, Lillie,"

Ash's stomach rumbled, and he shrugged, "Well, I mean, it has been a while since I've had anything,"

Lillie laughed, "Come on, let me show you where the kitchen is,"

Later that night, after a few games of cards and a celebratory dinner that included a bottle of champagne that Lusamine was saving (Goh and Gladion had way too much to drink)

It was time for bed, and Ash was shown what used to be an officer's quarters on the ship. A nice and relatively spacious yet spartan room.

Ash closed his eyes, trying to fall asleep. They'd be in Alola tomorrow afternoon, so he had a large day ahead.

Yet, no matter how hard he tried, he couldn't find sleep; his mind kept drifting back to Lillie and their reunion. He was no stranger to reuniting with old friends, from Misty in Hoenn to Dawn in Unova; he always appreciated seeing them again.

And as recently as two weeks ago, running into Serena in Hoenn was something else, he could tell that she wanted to spend more time with him, and he had a good idea as to why. He hadn't talked to her for over thirty seconds ever since "the airport incident" back when he was 17.

Ash sighed; why did girls have to be so complicated?"

He looked around his quarters. Pikachu was sleeping peacefully, curled up alongside the rest of his team. Even Dracovish was calm for once.

It was dark outside, but Ash figured the temperature would be significantly warmer, considering they were close to Alola.

Ash opened the door to his quarters carefully, making sure not to wake any of his pokemon.

Ash tiptoed around the lower decks and kept walking quietly towards a staircase so steep it could be considered a ladder. Ash climbed up it and unsealed the hatch, opening him up to the outside world.

The air was cool and refreshing, yet just moderate enough to not be considered cold. In other words, it was perfect weather.

Ash walked towards the bow of the ship and leaned over the railing.

It was peaceful, and maybe the fresh air would make him drowsy enough to the point where he'd be able to finally fall asleep unless he kept thinking of Lillie and stayed awake.

Suddenly, Ash heard some steps behind him.

Ash whipped his head around, expecting pirates or some pokemon, but was instead greeted by the person who he was thinking about.

"Hey," Lillie said with a whisper, trying not to wake anyone up.

"Hey," Ash replied, his heart speeding up for some reason.

"Why are you here? It's late out; you should be asleep," Lillie said

"I could say the same for you," Ash replied to her.

"Fair, but still. When you hear loud footsteps and the hatch opening, you can't help but wonder what exactly is going on. So I followed you," Lillie explained.

Ash snorted, "Sorry, I was going out of my way to be quiet; I guess that didn't work out all too well, huh?"

Lillie shrugged, "Eh, I mean, it's no big deal; I was awake anyway. Big day yesterday, and another big day tomorrow,"

Ash nodded, "Yeah, I get that, kinda the same thing here,"

"Then why come outside?"

"Reminds me of when I used to camp outside every day with my friends when I was traveling, back when I was a kid, sleeping in the woods every day without a care in the world, just chasing some gym badges and being excited about meeting new people and pokemon,"

"Oh, did you not sleep well in Alola?" Lillie asked

"Nah, I spent all day outside, so I didn't really notice it when I slept at Kukui's place. I guess spending all day below decks today kinda messed me up," Ash said with a shrug.

"Hmmm, well. I guess I'll stay out here until you're ready. I'd feel pretty bad if a Gyarados sprang up and ate you," Lillie said

"Yeah, I didn't wake up Pikachu, so I guess the company is nice," Ash said, joking around.

"Am I not as nice as Pikachu?" Lillie replied

"Sorry," Ash said with a shrug.

Lillie laughed and shoved Ash gently.

Ash looked up, noticing how the sky was full of stars.

"Woah! look up," Ash said, his voice full of awe.

Lillie looked up at the sky and immediately began pointing out constellations, which Ash appreciated.

"That right there is the Lucario, and that one is the Braviary, and that one is the Charizard," Lillie said, pointing to various groups of stars.

"What about that one?" Ash asked, pointing straight behind him.

Lillie turned around and paused for a moment. "Well, that's the Dragonite,"

"Huh, I wonder if there's a Pikachu one," Ash said curiously.

"Yeah, there is one, but only in the southern hemisphere," Lillie said

"Huh, well…..what regions are in the southern hemisphere?" Ash asked

"Just Hoenn and some region that people only call Pokespain," Lillie said

"That's a weird name," Ash said

"Well, maybe they'll change their name in a few months," Lillie replied with a shrug.

"Wonder if there's any new pokemon there?" Ash wondered

"There always is; you know how it is when a new region opens up contact with the outside world, it seems to happen every few years at this rate," Lillie said

Ash just nodded

The two sat in comfortable silence for a few moments before Lillie finally found the courage to ask Ash a hard question. A question she's been seeking an answer to for a long time. And this was as good of a time as any.

"Hey Ash," Lillie asked.

"Hmm," Ash hummed back.

"Have you ever….liked someone?" Lillie asked nervously

Ash's heart practically exploded, and he could feel his palms getting sweaty.

"Well, I guess I gotta be honest….. There's been two,"

"Oh,"

"You remember Misty, right? When I first traveled with her when I was younger, I guess you could say that I had something for her; she was my best friend at the time, and…. She was just there. It wasn't the same after she left, though, and when she visited a few months ago, I didn't feel anything like that," Ash explained.

Lillie nodded, "Makes sense,"

"As for the other, well…. I guess I'm still figuring that one out," Ash said. He didn't want to lie to her, but…. It was hard to tell the flat truth that he had real feelings for her.

"She's special, and it's been a joy to watch her grow as a person and as a trainer, and I only hope that she sees me the same way how I see her, as a good friend and someone who maybe would want to be something else one day," Ash said, voice full of some unknown emotion.

"Well, whoever she is, she is one lucky girl; a guy like you is a catch," Lillie said, trying to hide the sadness in her voice, assuming he was talking about one of his other friends.

He had traveled with so many other amazing girls; she didn't stand a chance, did she? After all, a member of the Master Eight could have nearly anyone they chose.

Ash took a deep breath in, and this was his chance. He was going to pull a Serena and pull off an unexpected action that got his feelings across.

"Yeah, she's really lucky; in fact, she's right in front of me," Ash said

Lillie's face practically exploded, and Ash leaned in, setting his lips on hers.

Ash pulled away after a minute, and Lillie was blushing as red as a cherry.

Lillie pulled Ash into a hug.

"Lillie, I….." Ash wasn't sure what to say

"I like you, Ash," Lillie confessed

"So….what now?" Ash asked

A strong gust of wind roared across the deck, causing both to shiver.

"Let's head belowdecks," Lillie said

Ash nodded and opened up the hatch for her.

After they were both securely below deck, Lillie grabbed Ash's hand and led him into her room.

They closed the door, and Lillie made sure to lock it.