AN: Okay, if anyone can find (or can draw) a May in Alola fanart, that would be absolutely wonderful! It makes me sad that there are barely any! These chapters will be a little shorter compared to my usual work, however, hopefully that will mean I can dish them out quicker! It will start off a little slow, but things will pick up as soon as I get the beginning out of the way. Enjoy!

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2. Vacation. 934
17 March 2017

Ash grinned, taking another big bite of his malasada. He watched May's face light up as she devoured her food too. He looked down under the table and smiled when he saw Pikachu, Rowlet, Rockruff, and May's glaceon, eating their pokemon food. Ash chuckled at Rotom continuing to add more information on glaceon.

"You were right, this is great! I love it! Especially after a fun swim! I am definitely getting seconds!" May exclaimed, the soft dough practically melting in her mouth as she savored the flavor. Ash nodded, knowing exactly what she meant.

They had spent the whole weekend relaxing and enjoying their time together. May merely came for a much needed vacation after everything she heard from Ash about Alola on video calls.

Ash looked at her curiously.

"So, are you still bummed out about the Grand Festival?" Ash asked, hoping it was alright to bring it up. He knew losing was a sore spot, especially for May. Pikachu looked up, his ears perked and listening in. Ash watched her intently. May sighed, her eyes looking poignant, yet still a bit hopeful.

"I think I'm always going to be a little sad about it. It was the closest I've ever gotten to winning, after all. But I guess the only thing I can do now is just keep going – well, take a nice break, first," she corrected, taking another big bite of the malasada. Ash grinned, nodding.

"I know what you mean. I needed a break too."

"I can see that – very long break, I take it. Beautiful place to take it too," May said, looking out of the malassada café to watch the ocean.

"Hey, I'm still learning a lot and catching new pokemon!" Ash reasoned. May merely nodded, however, giving him an unsure smile.

Still, he seemed happy. Her smile brightened, digging through her bag before taking her piece of the terracotta ribbon out and presenting it to Ash. The look on her face seemed to ask if he still had his half of the ribbon. Ash's eyes showed awe for a moment at the shiny ribbon. Ash's grin grew wider, seeming to answer with a wholehearted yes. His eyes brightened at the sight of their old trinket that meant so much to them.

"Hey, but let's not make that break too long though, yeah?" May asked, giving him wink. Ash nodded, reaching into his pocket before taking his half of the ribbon out.

"Definitely not. I still want to be a pokemon master, after all!" Ash reassured, moving his piece of the ribbon closer to hers, it finally becoming whole once more.

May nodded, happy to hear that. She was even happier that Ash kept his ribbon so close to him, however. This fact caused butterflies to flutter in her stomach and her heart to race at the very idea.

She kept her ribbon so close to her heart, because it eased her uncertainty and her anxiety before every contest.

She loved it, because it brought her hope and reassurance before every battle, before every performance, through every night alone.

Just thinking back to the days May spent training or the stories Ash told her of his hard work through Kalos continued to exhaust her.

Yeah, they both definitely needed a break.

However, May found it odd that the reason Ash stayed in Alola was for school of all things.

"Ash, I never expected you to stay in Alola for school," May pointed out. Because really, it wasn't like Ash. He would rather be going around a region and traveling and discovering new pokemon as he moved forward. That was the key word, he would always move forward.

Staying stagnant, not planning to join a league in a new region, was something that was unheard of for Ash.

"Hey, it's a pokemon school! It's actually really great. I'm learning a lot about all kinds of new pokemon. Plus, there are so many new ones; Alolan versions of the Kato pokemon here, too," Ash retorted, grinning stupidly. May smiled, knowing this was the same ole' Ash, at the very least. Same ole' Ash who loved pokemon more than anything, who would fight tooth and nail to help them out. "Hey, you know, you should check it out tomorrow! You should stop by the school!"

"Oh, so you're not going to ditch school to extend this little vacation time?" May teased.

"It'd be fun to hangout more, but I don't want to be absent from class either," Ash tried to say. May giggled.

"Look at you, Mr. Goody Two Shoes," May continued to tease. Ash began to childishly pout without even realizing it. He continued to do so until his face light up, a bright idea surfacing to the forefront of his mind.

"Hey, you know what? Why don't you just come to school with me tomorrow? You gotta meet all my new friends!" Ash explained, excited with his idea. Pikachu instantly jumped up, excited with this as well. May giggled, nodding in agreement, although mentioning how she was never the best when it came to school. "You'll see! You'll have loads of fun!" Ash reassured.

May thought for a moment, wondering if she should.

"Yeah, I'm definitely going to school with you tomorrow!" May smiled, beaming at the boy. Ash and Pikachu cheered, happy that she would meet all his new friends. He got so excited, he began to talk all about all of them – Mallow, Kiawe, Lillie, Sophocles, and Lana.

May nodded, not sure what to expect tomorrow, but none the less, she liked the idea of this new development.

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Important! Okay, so I love it when you guys give your input, so I will ask some questions and would love to see what you all think! And I was mostly writing this because I wanted to read a May in Alola fic, but it looks like many wanted to see one. This one, I wanted it to be based off the anime, however, many of you came up with really great ideas already (and it will also have a lot of game elements to it that aren't in the anime). If there is anything else in particular you would like to see in this story, please let me know!

1. What pokemon do you think May caught in Johto (for Johto I'm thinking pokemon other pokegirls haven't caught yet – I already decided on two pokemon, but would love to know what you guys think)? How about what she should catch in Alola?

2. Do you think I should include something that is not in the games (like contest) for May, or no?

3. I'm using the 100themechallenge themes to write these. So the most chapters this can have is 100, but honestly, that might be too excessive. I may pick 30 or 50 to use for this story, depending on what you guys think.

Your input means a lot! Till next time!