A/n: This is my first Pokemon fic! Anyways, this is a Contestship and Pokeship fic!

Summary: Ash and company have noticed something between May and Drew. Heck, even Harley and May's mother have seen it! So now, Ash has called an "expert" on love to come and help them get May and Drew together! Contestshipping and AAML.

I don't know where the real Kanto Pokemon Contests are, since the episdodes didn't air in the US yet. But I know that the contest in Saffron City is an accurate contest.

Disclaimer: I do not own Pokemon, or anything that has to do with it.

Hope you like it!

Story: Playing Matchmaker

Chapter 1: Let's Call the Expert

A group of two kids and two teens were staying in a room at the Pokemon Center. A boy with black hair was lying down on his bed, waiting with a small boy and an older boy for the bathroom door to open. Inside, the small boy's sister was taking one of her usual long showers that got the boy with the black hair, named Ash, impatient. His yellow mouse pokemon, Pikachu, continued to sleep on the bed next to him.

"Why does she take so long to use the bathroom?" Ash grunted. They had already taken showers and were dressed up, but Ash needed to use the bathroom again.

"That's what May usually does at home too." May's little brother, Max, replied.

"I guess all girls do that." The older boy, Brock, said.

May's ribbon case was on the desk in between the two bunk beds. Inside were beautiful ribbons that she won in Pokemon Contests. May, a very good coordinator, participated in the Grande Festival months ago, before Ash participated in the Hoenn League. Max looked at the case and remembered about Drew, May's rival. Drew was also at the Pokemon Center, to rest up before he gets back on his journey. This gave Max an idea.

"Hey guys, what do you think of May and Drew?" Max asked mischievously. This gained Brock and Ash's attention.

"Uh...they're rivals?" Ash asked. Max and Brock fell anime style.

"No. I mean...do you think that they could be more than friends?" Max asked again.

Brock smiled. "Well, we always see May coming to us with a rose in her hand and we always see Drew in the distance, so we know the roses always come from him."

"And he always shows off in front of May too." Ash said.

"If Drew and May were together, they could not only be more than friends, but help each other in contests!" Max said. "And, they could be one of the best coordinator couples in the world!"

"Not to mention Drew would stop showing off in front of us." Ash said. The three of them smiled.

"You thinking what I'm thinking?" Max asked and they nodded.

"Yeah." Brock replied. "But how're we going to get them together in the first place?"

A light bulb lit up in Ash's head. "We should get an expert to help us!"

Brock smiled and raised his hand. "That's me!"

Max then put Brock's hand down. "Yeah right. We need someone else. Someone we know. Someone...who has done this before and succeeded..."

"I have an idea of who." Ash said and got up from the bed, causing Pikachu to wake up.

"Pika?" Pikachu asked in confusion.

"Oh, good morning Pikachu." Ash greeted. "We're just going to call an old friend of ours before May gets out of the bathroom, which would probably be in 30 more minutes."

"Pi." Pikachu said and jumped onto Ash's shoulder. The four of them left their room and went to the main lobby where Nurse Joy was. She was sitting at her desk and using the computer. She looked up to see the four of them walk out of the rooms and look around the room for something.

"Good morning everyone!" Nurse Joy greeted. "What are you looking for?"

Ash sighed. "Nurse Joy, do you know where your phones are?"

Nurse Joy smiled and pointed at the line of phones. "There they are."

The four of them thanked her and went to one of the phones. Ash sat down on one of the seats in front of the phones and dialed a number. Brock, Pikachu and Max didn't know who he was calling, but waited for a response from the person Ash called. The screen lit up and a girl with orange hair appeared.

"Wow! Hey you guys! Long time no see!" The girl greeted.

"Hey Misty." Ash greeted back. "I was calling to ask if you can help us play matchmaker."

Misty raised an eyebrow. "Matchmaker? Who are we going to get together?"

"May and Drew." Max replied. Misty looked at them in confusion.

"Who's Drew?" Misty asked.

"Drew is a coordinator like May. They're rivals, but we know there's something between them. He always gives her roses but he always shows off in front of us, and especially May." Max explained.

Misty thought a bit and smiled. "Well, you're just in luck! They just built a few Pokemon Contests near Cerulean City, Viridian City, Cinnabar Island, Saffron City and Pallet Town. And guess what! The contest in Cerulean City is for partners only! Hmm...is Drew with you?" Brock nodded. "Then it's settled then. Once you need to do what you need to do, get May and Drew to come with you back to Pallet Town. Then we can go to the contest there, and get May and Drew to pair up for the contest in Cerulean City. I'll come along, since my sisters are back in the gym again."

"Alright! Thanks Misty!" Ash exclaimed and Misty smiled as they hung up. As soon as Ash got up from his seat, the four of them began cheering and jumping. Pikachu needed to hop down from Ash's shoulder so he wouldn't get dizzy. May had finished taking a shower and walked into the lobby to see them cheering.

"Uh, guys?" May started, startling them. "What're you guys doing?"

"We have good news!" Ash replied. "There are Pokemon Contests back at home!"

May began to smile. "Wow! Really?"

"Yeah!" Brock replied. "We should all go to Pallet Town and meet up with everyone and you can participate in some of the contests!"

Max thought of something and became as happy as Ash and Brock were. "Yeah! We should get Drew to come along!"

As soon as May heard that, she froze and widened her eyes. This was the reaction that Max was waiting for. Many thoughts appeared in May's head. Should they let him come along? He might win everything, but he'll be there with her. If he didn't come, then not only will May be able to win most of the contests, but be without Drew's presence. Ash and Brock noticed that she was thinking hard and was slightly blushing. May blinked and looked up at them.

"I guess we should invite him to come huh?" May replied and noticed Drew come out of his room and walk into the lobby. He went up to Nurse Joy and saw her get up and go to the back to get his pokemon.

"Why don't you go ask him?" Ash asked May. May froze again, but slightly nodded nervously. She walked over to Drew, who didn't notice her walking up to him. As soon as he felt a presence come towards him, he turned around to see May.

"H-hey Drew." May greeted.

"Hey May. I see you've brought your friends along too." Drew greeted.

"Oh, yeah. Well, my friends just told us that there are Pokemon Contests in Ash and Brock's home region and we're wondering if you'd want to come along." May asked, clearly.

There was silence between them. Drew was deep in thoughts and looked up at May. "Okay. Sure. When are we going?"

Ash, Brock, Max and Pikachu walked towards Drew. "Tomorrow at 12. There's a plane leaving nearby for Pallet Town, which is my hometown and where a Pokemon Contest is. We can all sleep over at my house."

Drew smiled and flipped his hair. "Okay. Hope I don't get as many fans over there than here. I had someone stalk me on the way here."

May became a bit angry at the fact that Drew was showing off again. "We'll meet back in the lobby tomorrow morning at 11:30."

"Alright. See you later." Drew said as he received his pokemon from Nurse Joy. "I'll be training for the pokemon contests for now. Bye May. Hope you don't lose as much as you did in Hoenn."

Drew left the Pokemon Center and went to a certain spot outside. He released his Masquerain and Roselia to train.

May was growling but slightly blushing. "Grr...can you believe the nerve of that guy? For once I just want him to shut up! I hate him!"

Nurse Joy heard all that she said. "May, are you sure that you hate him? Like they say, the one you hate is the one you love."

May began to blush more than she already did. "No! I don't love him!" This caused Ash, Brock, Pikachu and Max to laugh. "Stop laughing at me!"

Nurse Joy then handed everyone their pokemon. "Well, you should practice for the contests now too. You never know how hard it'll be to win a ribbon in Kanto."

"Yeah I guess I should." May replied and went back to the room to get her belongings. She went outside and noticed Drew working really hard.

"Razor Leaf Roselia!" Drew exclaimed. "And use Quick Attack to dodge them Masquerain!"

Roselia put its two roses together and sharp leaves shot out of them, elegantly shooting themselves with a little sparkle at Masquerain's direction. Masquerain dodged all of the sharp leaves using its Quick Attack. Roselia stopped its Razor Leaf and Roselia and Masquerain smiled.

"Good job you two!" Drew exclaimed. May just continued to watch from afar and sighed.

"When am I ever going to tell you?" May asked in a small voice that only she could hear.

A/n: There goes the first chapter! Will Ash and the others succeed at getting Drew and May together? Or will Drew continue to be just a rival to May? Next in Chapter 2!

Chapter 2: Plane Ride to Kanto

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