(A/N) I did this in one sitting (sort of) because that's generally how these type of things go for me. I've been in a major Advanceshipping mood lately since I just rewatched movie 9, hence this.

Enjoy!

They had made a pact the eve of their separation to stay in touch; he was naturally optimistic about it, giving her his signature wide, toothy grin ("you'll do great there!") while she spoke with her motherly tone shining through the blinds of her saddened demeanor. She made him promise multiple times to not forget about her or to call every once in a while because she would be dying to hear all of the stories of the adventures and new Pokémon he would come across wherever he ended up. She also knew, thanks to the little voice singing in the back of her head, that regardless of what she goes through next, it'll never compare to the lifetime of experiences he had given her. But she also knew that she had to branch off, go on her own and discover herself, to fully evolve to her maximum potential. And as badly as she wanted to stay with him and continue learning with him and continue living with him, she had to leave. And he understood and supported her decision fully, which she completely expected.

She boarded the ferry, all of her Pokémon and younger brother in tow, and waved until her arm was ready to fall off and she couldn't see him or Brock in the distance anymore.

It's sad.

But it was time.

The first time they talked was when she landed in Olivine City. She called his home in Pallet Town, expecting to see the dark-haired boy on the receiving end, only to be mildly disappointed when his mother was instead the recipient of her excitement to be in a new place bubbling over the edge.

"Ash? Yes, he left a few days ago. You know him… comes and goes so quickly!" Mrs. Ketchum, despite having the most dazzling smile May has ever seen, couldn't conceal the slightest bit of heartache dancing in her dark eyes.

Ash has her eyes.

Mrs. Ketchum sighed, flashing her another smile. "He went off to the Sinnoh region! You might be able to catch him in Sandgem Town- that was the last I had heard from him."

So May did just that, and luckily was able to catch him before he had departed for the next destination in the foreign region.

She couldn't hold back the excitement anymore, so she gushed to him about how wonderful Olivine was and the new Pokémon she had never even seen before and he just grinned at her, telling her again and again how much she was going to love Johto.

Johto was where he really blossomed after all.

She eagerly awaited to hear the tales of what he had crossed thus far, and was disappointed when he dismissed the stories for another time, stating that he hadn't gotten much sleep and Team Rocket again and a lot of traveling in a short amount of time. And it was then that she was able to notice the dark bags under his eyes and those very eyes pleading to please not be upset but I am very, very tired. So she let him go, wishing him luck and asking to chat again soon.

"Wouldn't miss it for anything, May."

The second time they talked was with less positive emotions; a heavy raincloud had cast itself over her world, so when she was informed that he had seen what had occurred earlier that day, she prayed that he wouldn't dwell on it too much. Because the last thing she wanted to hear was how she would get them next time, and there's always going to be more contests.

And he had planned to do exactly that, prepared to cheer up his close friend to the best of his abilities after closely watching a contest gone wrong for the brunette. His plan was brought to a screeching halt when she answered, and he was reminded how not very good at hiding emotions she was. Pain floated at the surface and he bit his tongue, because everything she said sounded forced and fake and it hurt him.

"We don't have to talk about it if you don't want to."

Her eyes shot up to his sharply, and he recoiled slightly, her pupils digging into his skin, slicing it open gently. It burned, and despite how much he enjoyed talking to her, he almost wished he hadn't called at all.

"There isn't much to talk about anyway. I didn't make it though the appeals round." She heaved a fatigued sigh, her gloved hand running through her brown locks. It was her turn to look tired, though Ash suspected this was exhaustion from having cried, something he knew she was a creature of habit with.

"It's the first contest, May."

"It's the first time I've lost in the appeals round," she spat, venom dripping off her tongue. She flinched after the words left her mouth, the bad taste lingering. She avoided his eyes, worried that her bad mood would rub him the wrong way. But when she gathered the courage to meet his eyes, she saw no animosity in them. Just warmth paired with a sympathetic smile.

"It's the first contest. You had a rough start. It happens to everyone."

She knew he was right; beating herself up over the first loss of her contest season would do her no favors. But it didn't help being alone.

It was easier when you were here.

The next conversation had them both in high spirits; he was riding the high of winning his third gym badge against the fighting expert Maylene, and she had arrived in town, brimming with elation for her upcoming contest the following sunrise. Life had plateaued into repetition for May: wake up, eat, train, travel, miscellaneous activities, repeat. She wasn't surprised to hear already thrilling stories from the Kanto native. He told her of the nightmare-inducing Darkrai, the story sending chills down her spine. She then chastised herself for getting too comfortable with the laidback lifestyle she was now accustom to; danger and excitement was attracted the Ash Ketchum like a moth to a flame, and she was almost jealous for now missing out on everything that used to add color to her previously monochromatic life.

He told her about his Pokémon, about the Chimchar that he had obtained from his rival. She heard about Buizel which had previously been owned by Dawn, the new coordinator who accompanied him.

May wasn't sure why her blood slightly boiled every time he mentioned the new girl's name. Her skin crawled and her eyes felt glossy and her mouth went dry- maybe because her name sounded so fondly in his voice and May misses when that used to be her name he would call out?

She was brought back down to earth when he continued on his rant about the blunette, stating how she hadn't been doing well in her contests lately and that it was obvious her self-confidence was plummeting ("maybe you could give her some pointers?"),and May felt her previous jealously dissipate into sympathy for the newly established coordinator.

The following conversation followed the previous closely, and had May chilled to the bone with her arrival in the freezing Snowpoint City. Despite hating the frigid temperatures- because Hoenn was a tropical paradise and she wouldn't have it any other way- she couldn't ignore the natural, untouched beauty the quiet city possessed. It had cast a spell on her and she almost felt remorse for cutting her stay so short. But she had accomplished what she came for and was prepared to head to the real destination.

Their chat was brief; she informed him of her arrival at the Valor Lakefront the following morning and he beamed at her, saying how happy he was to be able to see her so soon and see her perform again, and it made her chest feel warm and she couldn't stop the smile from stretching across her face.

She eventually had to dismiss him because she wanted to get her sleep and she knew that tomorrow was going to be jam-packed because Ash Ketchum was about to come crashing into her life again and she needed to prepare herself for a potentially one-sided emotional reunion. He, naturally, was unable to pick up on the hidden message she was trying to convey and released her, earning an eye roll from the brunette.

She called him when she had returned to the Pokémon Center in Olivine City, and Ash was glad to hear that her trip was smooth. He noticed however, that no matter how many times she told him the same thing ("it was so great to see you! You and Pikachu look as strong as ever...") he could tell she was hiding something. And halfway through their conversation, he noticed that she seemed almost full of regret for some reason.

"May, are you okay?"

She paused, her lips forming a taut line, and it was at that moment he could tell that she regretted leaving him for the third time now. That the same routine the two of them did, dancing around one another, was beginning to wear on her emotionally and mentally.

"It was a long trip back."

He chose to let the conversation die there, because an uncomfortable and unusual feeling rose within him, almost like he too regretted letting her leave him like that. He felt words again and again get caught in his throat since he felt it would be right of him to say he missed her and was sad to see her go but he couldn't figure out how to get the thought out into the open, so he dropped it.

She smiled wistfully at him, recognizing the emotion he wore on his sleeve being the same one possessing every fiber of her being at that moment.

The talk only lasted a few minutes longer, May telling him how she needed to go to bed because she had an early morning to begin the long trek back to Goldenrod City. He merely nodded in response and wished her a good night, wondering what had come over him then.

He was surprised and almost offended when he discovered Dawn chatting with her a few weeks later. They had paused for a break in a Pokémon Center in the middle of the route on their way to Celestic Town. Training had made up the duration of his schedule for the day when Dawn insisted that they took a break for relaxation, so when he found the two girls jabbering away about contests, he tried to not take it personally.

He soon found the two bouncing ideas and combinations back and forth and he remembered when him and the brunette did that with one another; he remembered the pride he felt when she adopted the water and fire combination from one of his Battle Frontier matches and utilized it masterfully in the Grand Festival in one of the most important matches of her career.

His memories were cut short when the blunette waved him over with a grin, asking him to take her spot while she went off to train with Piplup.

"I have just got to try the combination May was just telling me about! I'll catch you around!"

The coordinators bid each other farewell, and then it was just him and her.

May offered him a knowing smirk before speaking. "Training the day away, huh?"

She knew him so well despite being hundreds of miles away and that very thought brought heat to his face that he would prefer to stay distant. He felt warm and fuzzy and very confused because every time they talked now, he found himself feeling stranger and stranger and he needed to focus on his goal.

But then he looked so forward to hearing from her.

He was proud to witness her breeze through her contest, securing her fifth ribbon and entry into the Grand Festival in Johto. She commanded the stage and his eyes never left hers for a second as she performed, her Beautifly twirling methodically around her center stage.

It was as if he was actually there.

She's gotten so good.

So amazing.

Naturally, he immediately sat at the phone and called her, pleased and focusing all his energy on not letting the rose-color settle on his cheeks when she answered, eyes shining and absolutely beaming because she did it again and she has another chance for greatness.

He already thought she was great as she was.

He let her control the conversation, going on about the competition and how great it was to compete in a contest sans rivals for the first time in forever it felt like. She mentioned Drew and his newly obtained Houndoom, and how Harley has finally surrendered any shenanigans but proved himself more and more with each encounter to be a formidable opponent. She went on to talk about her team and all the hard training they were doing ("I almost feel like a mini Ash Ketchum!") and how she was dedicated to finishing what she started with the team who's been there with her since the beginning.

And he couldn't help but be glad for her and so proud of how much she's grown.

But remorse tickled him in the back of his mind because part of him felt that maybe she was only able to grow this much because she moved on without him.

She called because she had a cold, and luckily the grand festival wasn't due for another two and a half weeks because she was finally ahead of the game for once.

He gave her a smile of pity when she sneezed, her nose a bright red and her voice hoarse and dry and distant sounding. It made him wonder if he ever saw her ill when they traveled together; he felt as though she was picture perfect health and he never quite understood how but he didn't question it. So seeing her undone, all barriers down, made him feel slightly honored that she was okay with letting him see her like this.

She asked about the gym challenge, to which he happily reported that he had just obtained his final badge, not to mention along with a strong new asset to the team in the form of Torterra.

May beamed in return, congratulating him before getting thrown into a coughing fit, and he couldn't stop the small snicker from escaping him.

She merely glared in return, any energy she had left not being enough to throw jabs at the dark-haired boy.

"Time for another league?"

His eyes glimmered in response, making up for the lack of words.

She knew that nervousness was not a part of Ash Ketchum. And while the normal outsider would assume so from the silence, she welcomed the quiet with open arms. She knew the experienced trainer was containing all the excitement in the world for another chance at being the very best. And she then remembered that it would soon be her time too.

He immediately called, no hesitation included, in spite of being unsure of which direction to drive the talk they were about to have. If they would have it; he was fully aware that she was not always in the talking mood following these events, and he couldn't decide if he should be congratulating her for being the runner-up in the Johto Grand Festival, or if he should console her for being so close.

She answered, her eyes overcast, and he braced himself for what was to come. Ash opted for leaving Dawn and Brock in the dark about him calling her, figuring that it would be best to ride this solo. They all witnessed the close match between her and long-time rival Drew, who was able to narrowly escape defeat and take home the ribbon cup with him as result.

"What do you think?"

She was caught off by the simplicity of the statement, her eyes wide. "What?"

He offered her the same sad smile she always saw whenever these kind of things happened. "Are you happy you made it this far, or are you sad because you were so close?"

A moment of stillness passed between the trainers, and eventually an agitated sigh past her lips.

"Both?" She seemed confused, and he could understand why; he would be feeling the same way if put into the same position. "It's a very messy mix right now."

He said nothing, and she suddenly felt the lack of talking weigh down on her shoulders, heavy and relentless.

"I'm sorry I couldn't be there."

May blinked, unsure of what she just heard.

"Ash…"

The raven-haired boy huffed uncomfortably. "I wish I could've been there to support you."

The statement pressed down onto her body, and she felt herself growing closer to the ground below her. She didn't know what else to make of the statement asides from what it held at face value.

"I miss you."

There it is.

All air had been sucked right out of her as soon as those words left his mouth. She searched his face for the friendly look that was so common with Ash when it came to anyone that could be a friend; she expected the boyish grin and oblivious stare, but it was all missing. Replacing it was a look of pure affection, dusted with pain and thoughtfulness.

Do you?

"Do you mean that?" May whispered, unable to raise the volume of her voice any higher that what it was set at.

He nodded, saying nothing more.

Me too.

Olivine City was beautiful early in the morning before the sun commands the sky. The sunrise peeking over the horizon line of the ocean made May feel ready for anything. It was a gorgeous day for traveling, no matter how far. And she was going far, and nothing would be able to stop her. Her chapter in Johto had closed, the ending not being written exactly how she would have liked, but with an appropriate cliff-hanger to lead her into the next part.

Her decision was spontaneous, lacking structured plans. But perhaps that was what made it all the more tempting to her to follow though with. No one knew what she was doing, and she planned to keep it that way until she reached her destination.

She approached the ticket gate, ID ready in hand, smile present on her glowing face.

"One ticket to Sinnoh please."