Matchmaker

Because the one thing you need from me right now is a NEW story. But this one'll be short and sweet and completed (in fact, it pretty much already is). I promise. It was originally intended to be one of my FF vs. RL drabbles, but I liked the idea too much not to make it a proper-ish story.

DISCLAIMER: I don't own Pokemon, but given my inconsistent writing habits, aren't you glad I don't.

Summary: If there was one thing Ash Ketchum knew about . . . well it certainly wasn't matchmaking. And as well as the tried and tested clichés tended to work in movies, in real life, things tended to get a little . . . well . . . complicated. Pokeshipping w/ egoshipping on the side.

Matchmaker: A Cautionary Tale

Step 0 - The Plan

"So are you going to tell me who you like?" Ash asked as he placed a basic energy card alongside one of his Pokémon cards. Gary looked at it disdainfully, scoffing at Ash's choice of attack.

"What makes you think I'm going to tell you?" Gary asked in reply, placing his own card dramatically down on the floor in front of him. The two sixteen year olds were sat on the floor playing a fiercely competitive game of Pokémon trading cards, and as usual, Ash was losing badly. The Sinnoh Champion, either in defiance or despite his exalted position, seemed to be incredibly bad at the game - a game that was intended to mirror an actual Pokémon battle strategy as closely as possible.

"Isn't that why we're playing this game?" Ash asked, playing another poorly chosen card against his active Pokémon.

Gary rolled his eyes. "How do you even know I like someone?" he asked suspiciously, narrowing his eyes at his friend. "Who told you?"

"How do you know I didn't work it out for myself?" Ash replied defensively. "The way you've been mooning around this last week, it was obvious to everyone." Gary gave him a sceptical look. "Okay, it was Daisy," he conceded.

"That loose-lipped cow," Gary muttered to himself and thought of all the ways he would be able to get back at his older sister.

"Dude, you can't talk about girls like that," Ash reprimanded. "Especially ones that are related to you. Even I know that.

"And even if Daisy hadn't mentioned it, I would have worked it out for myself eventually," he continued in defence of Gary's loudmouthed older sister. "I'm actually really observant when it comes to relationships and stuff."

Gary only meant to scoff very loudly at the comment, but he couldn't resist the loud and obnoxious laughter that followed Ash's declaration. Who wouldn't? This was the boy who still didn't realize that each and every one of his female (and one male) travelling companions had been hopelessly in love with him and didn't realize that most of the females (and some males) that had offered him aid or shelter had simply been trying to get into his pants. At least, that was how Gary viewed matters. That point was that Ash wasn't 'really observant' about anything, particularly 'relationships and stuff'.

"I am," Ash protested once Gary had finally stopped laughing. "I was the first one to notice that Tracy liked Misty," he said, hoping Gary wouldn't notice the way his features suddenly darkened with jealousy.

"Tracy liked Misty?" Gary asked, the sour note in Ash's voice going unnoticed as he tried to hide a similar tone in his own.

"Yeah," Ash confirmed. "While we were in the Orange Islands. He was always talking to her, and they'd have these sort of secret conversations, and he was interested in all the same stuff she was interested in, and he was always making weird comments about her looks like 'I wish I had your figure' and stuff. I'm surprised nobody else saw it."

"Me too," Gary replied drolly, seeing the truth in Ash's uncanny observations. "Who's he seeing now anyway?" he added in the hope of maybe making Ash see the light.

"Um . . . Danny form Navel I think," Ash replied. "You know, now that I think about it, he had a thing for Misty too – that pedo letch. What kind of guy scams on a thirteen year old girl?"

Gary just nodded, smiling tightly. 'I mean, who am I to set things straight – so to speak – for Ashy?' Gary justified to himself. 'Rock boy should have explained this stuff to him years ago.'

"So, who do you like, Gary?" Ash asked, returning the conversation back to the topic that had begun it all.

"It doesn't matter," Gary waved off vaguely. "She likes someone else so it's not like I even have a chance with her."

"So you're giving up?" Ash questioned in surprise. "That doesn't sound like the Gary I know. Are you really gonna let yourself by bested by some chump loser?" he asked inspiringly.

"Not when it comes to Pokémon trading cards," Gary muttered under his breath as he finished the chump loser with a single card. "It's not like I haven't tried already," he said aloud. "You wouldn't believe the number of times I asked her out and she's seriously not interested."

"Well you're probably just going about it wrong," Ash assured him. "You can't just ask her out while she's hooked on this other guy. You've got to make her like you more than him."

Gary looked at him curiously, slamming his palm into his head a moment later for actually taking Ash's romantic advice seriously. "I can't believe I'm taking romantic advice from Ash Ketchum," he bemoaned loudly. "Remind me again what your credentials are, Ketchum? Who was your last girlfriend?"

"Well nobody," Ash replied sheepishly, blushing madly for no reason Gary could comprehend or cared to enquire after, "but I've got lots of girl friends," he added, emphasizing the disjunction between the two words. "I know loads about girls. I mean, I know Misty, and you don't really get more complicated than her when it comes to girls."

Gary nodded thoughtfully. Ash did make a good point about girls, and his close friendship with Misty put him in the prime position to offer advice. "Alright, Ketchum," Gary conceded. "What do you suggest?"

"Well . . ." Ash began thoughtfully, taking a moment to consider what was best. "I think what you should do is offer to help her get with this other guy . . ."

"What?" Gary exclaimed. "Are you serious? Why on earth would I help the girl I like get with another guy? It's ridiculous!"

"No, hear me out," Ash protested. "It works all the time in books and movies and stuff. See, the two of you will spend time together while you're scheming and because of that she'll develop feelings for you instead of the other chump. It's a guaranteed success. Misty's made me see a million movies like it with her and they all work out the same. The girl always ends up with the guy that tries to help her get the other guy. It's inevitable."

"Big word, Ketchum," Gary antagonized. "Do you even know what it means?"

"It means it's going to happen," Ash said surely.

"You so better be right, Ketchum," Gary warned. "Cos if it doesn't . . ."

"It's gonna work," Ash promised. "I guarantee it."

~ to be continued ~

Interesting start, right? I think there are two people you can take romantic advice from in Pokemon and just know it's going to end in disaster - one is Brock and Ash is the other. This story is short and sweet and almost complete in my writing of it, so it'll be weekly updates for this one. Let me know what you think.