Matchmaker

I guess you all liked the first part well enough, so here is the next installment. Hope you enjoy.

DISCLAIMER: I don't own Pokemon.

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 1 - Put Into Practice

Ash's plan was ridiculous. Gary knew it was ridiculous. But he didn't have a better plan so he thought, 'what the hey? Let's see if it works'. If it did, it did. And if it didn't, then it wasn't like he'd really lost anything. He'd simply be right where he started – no better or worse – only this time he could blame it all on Ash. That, he considered, was a win-win situation.

And so, with Ash's plan only vaguely outlined in his head – after all, he couldn't give Ash the necessary details for cementing the plan without giving himself away – he made his way to Cerulean City to make a fresh appeal for the current love of his life. He was met at the front door by Misty's eldest sister, who – as always – greeted him with a flirtatious smile that he knew better than to give serious thought to. He knew far too many guys who had been burnt by Daisy Waterflower to believe that a flirtatious grin from her meant anything more than extreme friendliness.

Of course, that didn't stop him from flirting a little back. "And how are you today, Miss Daisy?" he asked dapperly. "You look lovely, but that's not all that unusual for someone as naturally lovely as you."

"Charming as always, Gary," Daisy grinned back, a gay laugh lilting the air. "I suppose you're like here for your bi-weekly rejection?" she asked him with amusement lighting her blue-green eyes.

"What can I say?" Gary shrugged, a lazy grin on his lips. "I'm determined to succeed."

Daisy scoffed in a surprisingly adorable way. "I'd say you're a masochist, Gary Oak," she told him. "I think you almost enjoy it," she added with a seductive wink before turning suddenly teasing. "Unless you're like really here to see me and this business of asking out my baby sister is just like a cover."

She chortled at the thought, turning away from him momentarily to make a loud cry out towards the back reaches of the gym. "Misty, you've got like a gentleman caller!"

"Yeah, I noticed," Misty replied dryly. She entered the room immediately after Daisy's cry, tying up her hair on the top of her head as she walked.

"Does this mean you've started to anticipate my visits, Red?" Gary asked with a smile as he drifted away from Daisy and towards the current object of his affections. He turned his charm up to its highest level, knowing anything short of maximum charm would be completely ineffective on Misty.

Misty sneered at him, the nickname alone making her practically gnash her teeth. "It means I've come to associate the sudden cloud of smog and the waft of cheap cologne as indicators of your presence," she told him snarkily and crossed her arms tightly over her chest. "Don't think for a second I'm happy to see you."

Gary looked unaffected by her harsh words. "You say that now . . ."

"And I'll keep saying it until you get the hint," she finished for him, scowling to prove her point. "Can we just get this over and done with so I can go back to my training? I think I've almost made a breakthrough with Psyduck's swimming lessons and Gyarados is in desperate – deserving – need of my attention."

"I guess," Gary conceded reluctantly, Misty's impatience somewhat disheartening. "I actually came today to offer you my services," he said, doing his best impression of shyness.

"Well that's a new one," Misty muttered sarcastically, rolling her eyes. "In case it wasn't obvious the million times before now, I have no need, desire, or interest in any services you have to offer," she told him pointedly, a sharp gesture of her hand emphasising each word and her lip curling in disdain as she spoke.

"You didn't even hear what they are," Gary protested weakly.

"Oh c'mon, Misty. Just give him a chance," Daisy encouraged. "Go on, Gary," she suggested before Misty could interject and disparage him further.

"Right," Gary began awkwardly. He had forgotten that Daisy was still there as he tried to convince Misty of his good intentions with all the subtlety of an antelope at a hunting convention. "I wanted to . . . uh, help you . . . with Ash."

"What about Ash?" Misty replied with a glare. Her voice dropped dangerously low and her jaw clenched. She was clearly still in the denial phase.

Gary rolled his eyes. "Let's just pretend for a second that you liking Ash isn't the worst kept secret in all of Kanto," he replied sarcastically. "Ash and I are friends, and I've known him longer than you and Brock combined, so I'm in the prime position for helping you win Ash's heart."

"I'm not . . . he isn't . . . and a-and I . . ." she spluttered adamantly, her flushing cheeks defeating any argument she was trying to make. "I have no interest in Ash's heart," she said snootily as soon as she found the words, the threatening look in her eyes just daring him to say otherwise.

"Except you totally do," Daisy answered unhelpfully on Gary's behalf. "And Gary is being totally helpful so like stop being such a bitch, baby sister, and just accept help when it's offered to you."

Misty gaped at her sister, unable to believe that Daisy was being so forthright and taking Gary's side. "Fine, whatever," she muttered with a wave of her hand. "Do what you want."

Gary beamed, phase one of his plan (well . . . Ash's plan) a complete success (relatively). "You won't regret this, Misty," he assured.

"I will," Misty muttered darkly in reply. "I can almost guarantee it."

Gary tensed. He felt a strange need to back away slowly when that tone reared in Misty's voice, and he could tell that Daisy was having similar thoughts as she made desperate glances towards the three exits in the room. She almost jumped out of her own skin as a figure appeared suddenly in one of the exits, carrying two fishing rods (one full sized and one miniature) over his shoulder.

"Hey, Myst! Do you wanna go fishin'?" asked a loud and naturally boisterous Ash as he walked into the room with his prized Pokémon, having made his way into the gym without any of the polite pretence Gary had used to gain admittance. He grinned at his best friend, waving the fishing rods at her invitingly and remaining completely oblivious to the tension in the room . . . or the way it seemed to spike with his sudden presence.

"Oh hey, Gary. What are you doing here?" he asked as he noticed he other occupants in the room. He offered Daisy a polite wave, but for the most part ignored her without the slightest guilt.

"Just running an errand for gramps," Gary lied.

Ash nodded without giving it any further thought. If he had, he'd wonder what sort of errands Professor Oak could possibly have in Cerulean two days running, as Tracy had been sent on some business just yesterday morning. Instead he turned his attention back to his best friend, thinking of no one but her and her answer to his question. "So what do you say, Myst? I think I know a rock with your name on it."

Misty laughed happily at his goofball reply and untied her hair in a way that she hoped looked completely casual. She moved closer to Ash, her posture seeming to relax with his presence and a smile spreading across her previously grim features. "Like I need any more encouragement than that," she teased affably. Her whole mood seemed to do a complete turn around from dark and irritated with Gary to bright and happy with Ash.

"But, Misty, what about ps – " Gary began, trying to remind her of her duties to her Pokémon training that she had cited earlier in order to get rid of him. He was, however, stopped from doing so by a subtle kick to the shin from Misty.

"I'll just go get my stuff," Misty said. "Are we going to the usual spot? Or were you trying to catch something in particular?"

"Not really," Ash shrugged and followed her as she made her way out of the room. "Can't a guy just want to spend some quality time with his best friend?" he asked, nudging his shoulder into hers. "Well, best human friend," he added with a gesture towards Pikachu, who lagged slightly behind the pair in his proper fishing attire.

"Maybe, but I still suspect a motive," she replied with a laugh.

Gary's eyes widened in near panic as he watched Ash Ketchum flirt with HIS current love interest. He had to work to keep his expression neutral on seeing this, his only consolation being that Ash wasn't particularly good at flirting (a rock with her name on it – puh-leez) and that Misty was wilfully blind to the meaning behind Ash's actions and words. But no matter how bad Ash was with regards to the opposite sex, Gary was quite certain of what he was seeing and he knew he had to put a stop to it before it went too far.

"Hey, guys, do you mind if I come with you?" he asked suddenly, halting them in their path. They turned simultaneously, both giving him meaningful looks that seemed to say the exact same thing: TAKE IT BACK!

Ash's gaze shifted suspiciously as he desperately searched their surroundings for some kind of out. "I . . . uh . . . I don't have another fishing rod," Ash tried awkwardly, knowing immediately that it was a terrible excuse. They were, after all, in a Water Pokémon gym and the Waterflower sisters (Misty in particular) owned almost as many fishing rods as there were water-type Pokemon. "I guess Misty could lend you one," he added lamely, "so I guess if it's alright with her . . ." he said, hoping it wouldn't be.

"Well, if it's alright with you . . ." Misty responded with equal awkwardness, her words conveying to anyone just slightly less dense than Ash that it was not alright with her in the slightest. She glared at Gary, trying to mouth instructions to him of exactly what his response should be – something along the lines of 'you know what, I think I have another engagement so maybe another time' – while Ash wasn't looking.

"Cool," Gary said, ignoring both Misty's silent instructions and the various non-verbal cues from the two of them that said his presence was not wanted.

"I'll just get you a fishing rod," Misty replied tightly, her words seeming to imply a desire to impale him with said rod. She turned on her heel, taking Ash with her as she want to get what was needed. As before, they made subtle, intimate touches along the way – Gary, for the most part, already forgotten.

"Gary," Daisy started once she was sure they were far enough away, "you like better be serious about helping Misty, 'cos like if this is just some ploy to get her, it's not going to work. You're like not going to win. Not against Ash."

"Seriously, Dais'?" Gary replied casually with a half-laughing smirk on his face. "What do you think this is? Do you think I got romantic advice from Ash Ketchum telling me I should pretend to help her get with the guy she likes so that she'll fall in love with me in the process? That I'd go and base my whole premise for wooing her on a clichéd romantic-comedy plot that just barely works in movies? That's ridiculous, Dais'."

"You're right, that sounds totally ridiculous," Daisy giggled. "Like, what was I thinking? I think I've seen like too of those movies for my own good.

"I guess if you're with them now, you can like help them see that their feelings are totally mutual," she said, convincing herself of the plan even as Gary came up with his own, more devious version of how things would progress.

"Totally mutual," Gary muttered in agreement. He wondered how he'd managed to miss the fact that Misty's unrequited loved for Ash Ketchum wasn't quite so unrequited, especially given that even Daisy could see the truth. It was kinda obvious now that he realized it, because even though Ash never seemed to show any interest in his female travelling companions, he'd always had a special place for Misty Waterflower that seemed to go well beyond the realms of friendship.

Not that such a thing would stop Gary from trying his darndest to steal Misty right from under Ash's nose. As far as Gary was concerned, Ash had had his chance – he'd had six years of chances – and now it was Gary's turn.

And nothing was going to stop him from getting what he wanted.

~ to be continued ~

Uggh, I didn't want to write an evil Gary, but this story just went and took its own course. It was supposed to be slapstick humour, but somehow managed to gain a dramatic tone that I hadn't intended from the first chapter. And Gary's not entirely evil, just a little self-absorbed and not a particularly good friend, so he's only mildly OOC (at least with post-Johto Gary who was kinda OOC of the original series Gary - I can actually see the old Gary doing exactly this sort of thing).

So now that Ash's got some serious competition to contend with, will he finally step up to the plate and make a play for Misty's heart? Will Gary somehow prevent Ash from throwing his hat in the ring? Or will Misty's succumb to Gary's ingenious plan to distract her from her feelings for Ash?

Find out in the next stage of Matchmaker: A Cautionary Tale and in the meantime, review!