Title: Mismatched

Summary: Delia's unorthodox method of matchmaking was exactly what two clueless people needed to finally admit their feelings. #Pokeshippingweek2022 prompt "Delia the matchmaker."


"Hey Mom, whatever happened to my old friend, Leaf?" Ash asked curiously from the doorway leading from the garden into the living room.

He and Gary had thrown out the idea of a spar given the slow nature of the afternoon when the conversation of their mutual childhood friend had come up. Gary's commentary had unsettled Ash to the point that he had to pause their pursuit of a match and go to his mom for answers.

Delia looked up from the book she was thumbing through in her reading chair and almost spoke before being cutoff by the professor who had been pouring over research paper submissions on the couch adjacent to the coffee table.

"Say Delia, isn't she one you scared off because she liked Ash?" Professor Oak thoughtfully goaded with a grin.

Delia shot Samuel a glare while Ash turned curiously to the matriarch.

"Gary said the same thing...So it's true?" Ash asked, disheartened.

"She wouldn't have been good for you," Delia hummed nervously, clasping her hands in her lap after setting the book aside, "I didn't see how it could work out so I thought I'd save you the trouble."

"That time and half a dozen others," Gary muttered, following Ash into the living room and comfortably flopping onto the couch. He'd given up on the prospects of a proper battle with this newfound mystery at the forefront of Ash's mind.

"Mom," Ash asked cautiously, "how many times have you done this?"

"Oh not many, just the once intentionally...After that I swore to let you handle your personal affairs yourself, but..." Delia shuffled, having a limited propensity for perpetuating lies.

Like Ash, she could omit information, but outright lying required a herculean struggle.

"Who?" Ash pointedly queried.

Delia squeaked and made a motion to escape to the sanctity of the kitchen while Gary chuckled and lifted his hand.

"Well, let's see, most recently Serena, though I do have to agree with you on that one Mrs. Ketchum," Gary laughed rubbing his chin; he hadn't been the biggest fan of the demure but pretty girl that overly encouraged the brash trainer. Ash's ego needed deflating more often than it required boosting.

"How do you know?" Ash asked dumbfounded as to how Gary had more intricate knowledge on his failed love life than the trainer himself.

"They," Gary motioned to the professor and Mrs. Ketchum, "talk nearly every day. Your love life, or lack thereof, comes up from time to time."

"So why didn't you like Serena, Mom?" Ash puzzled; even he knew Serena had liked him. Well maybe he hadn't until she kissed him, but he figured it out eventually, and Serena was a nice girl so his mom had no reason to try and chase her off.

"Her life is in Kalos," Delia avoidantly answered, "you were naturally going to keep traveling so I just told her to skip the heartache that would come from distance and see if things would work out in the future; if you ever settled in one spot that is."

"Who else did you chase off?" Ash sighed realizing, while he wasn't heartbroken over the blonde's absence, this likely wasn't his mom's first offense.

It was Gary who answered again with a Cheshire grin. The taunting came from a place of knowledge driven power and despite the muted rivalry the two now engaged in, having the upper hand always provided a sweet sense of satisfaction.

"Dawn, naturally, though Mrs. K's plan to set her up with Paul was pretty ingenious," Gary addressed Delia with a bit of awed glee.

"Dawn's dating my rival? Mom, are you crazy? He's like 10 years older than her," Ash grumbled irritably; come to think of it he had no idea what was going on in Dawn's life as both trainers were too busy to keep in touch most days with only the wayward phone call as a means of communication.

"Well, Dawn stopped by Pallet on her way to Johto and I happened to invite her over for dinner. Paul also happened to be passing through town and Dawn had some sort of run in with Team Rocket in the forest before dinner that Paul helped her out with, so naturally she brought Paul along to dinner. And he's 6 years older than her, not 10," Delia corrected, "I'm surprised you didn't know. They've been traveling together ever since."

"Anyone else?" Ash muttered dejectedly, fully expecting the answer to be yes.

"Well there was Norman's girl, right?" Professor Oak interjected, "May, right? That was another one you played matchmaker with."

"May?" Ash smacked his forehead, "who did you set her up with?"

"That nice green haired boy, Drew I think it was. By the time she stopped by for a tea time I could tell she was very much head over heels for him. From the story I got from her, he was formerly her biggest rival," Delia explained, "she didn't have any feelings for you, so don't blame me for that one."

"So what I'm hearing is you've literally messed with the love life of everyone I've ever traveled with..." Ash muttered in annoyance.

Gary's boisterous laugh from across the room made a sudden thought strike Ash and he turned to his mother in panic.

"Mom, please tell me you didn't try to scare off Misty...that's not why she left, is it?"

Ash's voice had turned to a horror-stricken whisper as he recounted the loss he felt at the redhead's traveling departure.

"Ash, honey," Delia sighed, moving towards the boy with open arms, "I, um..."

"Mom...Please...not her too," Ash muttered fretfully.

"It's not why she left," Delia defended in a flat monotone dropping her arms back to her sides.

"What did you do?" Ash exasperated.

He could deal with his mom interfering in the lives of the others, if anything she'd done a fair amount of damage control to allow him to keep pursuing his dreams, but Misty was different. He didn't realize it until several more people had come and gone into his life and as he'd never had such an extreme reaction to losing a traveling companion before or after her, he figured it had to mean something. The more he observed and reflected on his own feelings the more confident he became that he actually harbored some long standing, deep emotions for the feisty redhead.

Gary and Professor Oak made a motion for the doorway as they knew the answer that followed this plea would come with a long overdue explanation and heartfelt apology that made them want to leave the family to their own devices.

"Well, I did say something to her," Delia sighed, dropping her hands at her side and watching the anger that flushed across Ash's face, "but, um, she didn't listen to me."

Ash looked at his mom dumbfounded. He shouldn't have been surprised, really. No one could make Misty's mind up for her.

"What?" Ash exasperated, struggling with the concept that his mom, despite knowing how he felt about the redhead, may have deliberately tried to sabotage his chances at a relationship.

"It was after you left for Hoenn; she called me one day during a long weekend off at the gym to let me know she would miss our usual tea time because of some commotion in Cerulean with the baseball game. Additionally this boy, Georgio, had asked her out on a date and she wanted advice on how to turn him down," Delia admitted nervously.

"So someone asked her out, big deal, she turns people down all the time," Ash grumbled, though his undertone had a bristled barb to it.

"I may have encouraged her to go out with him," Delia sighed watching Ash's crestfallen face, "she disagreed; she thought he was presumptuous and rude for assuming he could win a date with her and disregard her own feelings on the matter."

"He was," Ash griped sourly, "if Brock's taught me anything, it's when a girl says no, you respect that."

"That's what she insisted," Delia smiled faintly, "she also said if you tried anything like that, she would beat you with a mallet, which I knew she was joking about, but I understood her point."

"Right," Ash added dryly, rolling his eyes, 'joking', he inwardly smirked having faced her wrath on more than one occasion.

"She still turned the other boy down," Delia dismissed with a small shrug hoping to change the topic.

"So that's it? You encouraged her to go out with someone else and she still turned them down?" Ash asked skeptically.

It seemed to benign a response for the initial panic he saw in his mom's eyes when he mentioned Misty.

"Well, maybe there was a little bit more…" the matriarch mumbled with downcast eyes, "I asked why she brought you up when mentioning this boy who asked her out and she admitted to having a small crush on you. I just politely reminded her that you weren't going to stop traveling and she was stuck at the gym so she may want to consider other options."

"Mom," Ash whined, "I liked her too."

"I know, but I liked her and I didn't want her to stop coming over for tea because you did something dumb and ended up breaking her heart," Delia defended quietly.

"Why do you think I'd be so bad at things?" Ash muttered, "I'm not entirely clueless."

Delia chuckled lightly, "she said the same thing about you, though I couldn't tell if she was being serious or not."

"Do you think I still stand a chance?" Ash asked cautiously, from what he knew Misty still regularly had tea with his mom so if anyone were to know, it would be her.

"I'd say so," the elder Ketchum encouraged, "but know if you mess things up, I will still be seeing Misty for tea once a month."

"I'm not going to mess this up…" Ash insisted with a sigh, "at least not intentionally."

"Good," Mrs. Ketchum grinned, "now do you have a plan for how you're going to talk to her?"

"Mooom," Ash whined, "I'm not talking to you about this. It's Misty; we've been best friends since I was ten years old. I'm sure I can figure this out myself."


Two days later he was still scratching his head on how to even start to approach the vivacious redhead. He'd called her and let her know he'd be visiting Cerulean City in a couple of days, but didn't say why.

And Misty, knowing Ash's irregular and spontaneous schedule, hadn't even questioned it.

Still Ash was going in with no plan, which wasn't unusual for him, but the pressure was building as he and Pikachu took the two day scenic trainer route through Viridian forest to Cerulean City.

As he walked through the last stretches of dark forest, he bounced ideas off his loyal, yellow rodent since Pikachu was a trustworthy confidant and knew the water pokemon master in training just as well as Ash did.

"Do you think I should get her flowers or chocolate...girls like that stuff, don't they?" Ash reasoned hesitantly.

"Ka chaaaa," Pikachu shook his head adamently, "Pika pi pi chu."

"Yeah, you're right, that's too generic," Ash agreed with a slight nod, "how many guys gave her flowers when we traveled together and it didn't work out for any of them."

Pikachu nodded in agreement from his perch on Ash's shoulder.

"Pika Pikachu Pikachupi," Pikachu reasoned knowing Ash would understand the sentiment.

"You're right; I should do something with her instead of getting her something," Ash affirmed scrunching his brow as he thought, "but what?"

"Chu?" Pikachu offered up as a suggestion.

"Water?" Ash asked in reply, "what about water?"

Pikachu smacked his forehead before miming some suggestions involving water, of the few Ash understood seemed to be fishing, surfing, and swimming.

"OK, OK, I get it. She's happiest on the water, so I should aim for some activity involving water," Ash relented mulling over his options.

While he hadn't decided entirely, at least it gave him a place to start.


"Ash, what're we doing?" Misty curiously asked as that morning the trainer had showed up at her door with a determined look on his face and insisted that she close the gym for the day while he dragged her out toward the Cerulean beaches.

Stranger still, Pikachu had insisted on staying at the gym and catching up with her pokemon, though she wasn't sure if Pikachu was setting something up or if the little mouse just missed his old friends.

Ash had thought about insisting that Misty wear a swimsuit, but he confidently reasoned that she was always in some sort of swimsuit given she swam nearly every day so he figured it hardly mattered.

"You'll see," Ash grinned, pulling her along by the clasped hand towards a nearby cove.

Misty could definitively say that the only guarantee about going along with Ash was that it was bound to be an adventure, and the excitable way in which he'd grabbed her hand as he dragged her along the path out to the coast was reminiscent of their early days traveling together when he was so overwhelmingly excited about something that he couldn't help but pull her into it.

And in this case, as long as it wasn't a freshly caught bug pokemon that he was showing off, she was more than willing to let him lead.

If he somehow got them lost, she would definitely call him on it, after all.

"Here we are," Ash boasted with a certain grin as they stopped at a small shed on the side of the cove.

"Okay…?" Misty queried, still uncertain of the day's plan as the shed was a relatively new installment in Cerulean City. She was aware that the city had funded the project and these small sheds had been put up on the more popular pokemon catching beaches around the city as they were equipped with items free to rent for helping trainers have ease of access to the water, but up until this point she hadn't had the chance to personally check them out given her bustling gym leader life.

"I figured we might try looking for some pokemon while paddle-boarding," Ash grinned pulling out the two flat boards and a couple of double sided paddles.

He was grinning like a little kid so much so that Misty hadn't the heart to tell him this cove was pretty much just full of goldeen and seaking, with the occasional baby water pokemon, but she suspected that didn't matter.

She couldn't help but giggle as they set out on their paddle-boards and the dark-haired trainer clearly hadn't improved his balance over the years as he struggled to stand up and follow along with the redhead who gracefully paddled away from the shoreline.

"Try to keep up," She cheekily grinned tossing a glance behind her as she led the way to a series of nearby sea caves, knowing the challenge alone was enough to get Ash to focus and try harder.

She beat him by a good margarine, which he expected, but following her into the well lit cave system he found her sitting at the top of a red rock platform with her paddle-board pulled ashore at the bottom of the small rock scramble. Pulling his board alongside hers he clambered up to join her.

"Guess I should have known picking an activity on the water would mean that you would best me," Ash chuckled settling down into a seated position next to the smiling girl.

"Mhmm," Misty happily murmured staring out from the perch toward the entry to the cave system. She could see a small school of staryu's gems sparkling from the light filtering into the shallow entryway waters, "so why'd you really bring me out here today?"

"What do you mean?" Ash replied trying to act as clueless as possible, given his nerve was wavering.

"Your mom finally told you, huh?" Misty grinned nudging Ash's shoulder with her own.

Ash looked at her in surprise, "how could you tell?"

"You know how you suck at something until I make it a challenge?" Misty grinned, motioning to the paddle-boards sitting on the rocks below.

Ash stuck his tongue out in response, nudging her back.

"Maybe I laid out a challenge a long time ago, knowing eventually you'd rise to it," Misty teased, boldly facing the trainer she'd called her best friend for the better portion of six years.

"Is that so?" Ash replied, masking his nerves with false confidence.

"I'd also bet you're too scared to kiss me," Misty smirked, slightly moving her face closer to his. He could feel her sweet breath on his skin and without thinking he closed the small gap and captured her lips with his own in a chaste, but electric kiss.

When they broke apart after the brief dalliance, Misty grinned at Ash, "You sure you're up for the challenge of dating me?"

"Never met a challenge I wasn't up for," Ash confidently boasted, "but I have to ask...were you being serious when you told my mom you thought I'd be entirely clueless at all this?"

"Guess we'll have to see," Misty taunted moving back in for a longer kiss.


Hope you enjoyed!

Up next I'll have "Overprotective Misty" as the theme. I'm running behind on posting, but I'll post that one tomorrow evening once I get a chance to do concluding edits. I know Pokeshipping week technically ends today, but I'm still going to try and get the rest of my themes concluded and posted over the next week.

Favs and reviews are always appreciated!

-FWFT