Chapter 6


Saturday, September 10th

Dawn yawned audibly as she sat in her kitchen, quietly looking at dress designs on her phone. She was so glad that today was Saturday after having such a long night. It wasn't often that she slept in, but that was practically a requirement after the night she just had.

"Ah Miss Dawn, I'm glad to see that you've awakened." Darach greeted her as he entered the large kitchen.

"Good morning Darach." Dawn replied softly, giving him a small wave.

"It's almost eleven o'clock. Would you like anything for breakfast?" He offered her after glancing at the clock.

"Umm, I don't think so. I'm feeling fine right now. I might have an early lunch later on though." Dawn replied. Darach gave her a nod as he joined her at the table, taking a seat across from her. Dawn felt a chill run down her spine as she stole a glance at Darach, catching a glimpse of the stoic expression he wore as he observed her.

"Do you mind if I ask you a question, Miss Dawn?" Darach asked her, and this caused Dawn's heart rate to pick up. The way he was examining her, almost skeptically…it made her feel uneasy. Did Darach know anything about last night? Was he there?!

"Ah, sure." Dawn said, inviting him to proceed.

"Are you aware of the curfew your parents set for you?" Darach began, and Dawn already knew that her fate was sealed. Giving him a small nod, Darach then continued. "It's a generous time, so why would you choose to go out after your curfew?"

"How'd you know?" Dawn asked him first.

"I always check on all of you once you've gone to sleep, Miss Dawn. When I checked your room last night, I surprised to see that you weren't there. Where did you go?"

"I went to hang out with some friends. Believe me, that was a one-time thing." Dawn explained. She definitely didn't plan on seeing any more of Vermilion City's nightlife in the near future.

"And what about that young man you returned with this morning. Who is he?" Darach inquired as he leaned forward a bit. Dawn leaned back into her seat with a pout now since the entirety of her night out had been completely exposed by Darach. All of her careful planning had been spoiled on her very first attempt.

"His name is Ash Ketchum. We go to school together." Dawn said with a huff, causing Darach to perk up.

"Ketchum?" He repeated, getting a nod from Dawn.

"Mhmm, and he's pretty nice too." Dawn said before their doorbell chimed.

"Excuse for one moment," Darach said as he rose from his seat. He disappeared from the kitchen to answer the front door, leaving Dawn to drum her fingers on the table as she waited. Soon enough, Darach returned with another question for Dawn. "Miss Dawn, were you expecting company today?"

"I wasn't expecting anyone. Why, who is it?" Dawn asked in return as Darach beckoned for her to come with him.

"There's a young woman at the door requesting your presence." Darach explained as the two of them journeyed to the main entrance of the estate where Dawn found none other than Serena waiting there for her.

"Serena?" Dawn exclaimed at the sight of the familiar brunette who smiled upon seeing her.

"Good morning Dawn!" She said cheerily.

"I see, so this is another acquaintance from school?" Darach asked as he looked toward Dawn.

Dawn kept a neutral expression as she realized Darach must have associated Serena with Ash, assuming that Serena was also one of her peers. Dawn was ready to correct him but another thought occurred in her mind. Did she want to tell Darach that she had met Serena from the night before? She had already promised him that she wouldn't break curfew again, but mentioning that she was still associating with the people she had met last night probably wasn't the best idea. Dawn didn't need to have Darach being suspicious of her.

"Ye-up. Serena, this is Darach, my butler." Dawn said, introducing the man who bowed to Serena.

"It's a pleasure to meet you," Darach said as he straightened up. "Seeing as you have company, Miss Dawn, we'll drop the subject you and I were discussing and I'll give you some privacy."

"Thank you Darach." Dawn said as he left the two of them together at the front door.

Serena waited a few moments, watching Darach disappear into one of the corridors before she finally spoke again.

"Dang Dawn, Ash said your house was big, but this is huge!" She noted, looking around in awe. Dawn gave a sheepish chuckle in response. "What does your family do?"

"Oh, my dad is big on trade and commerce and stuff like that. Plus he owns the shipping yards downtown." Dawn explained, leaving Serena wide-eyed. No wonder they were so well off. "By the way, how'd you know where I live?"

"Ash texted me your address this morning. After what happened last night, he said you were a little shaky." Serena explained. "Miette and I were coming today, but she was called into work so I came by myself."

Dawn was touched that Ash's friends were willing to come all the way to her home to make sure she was alright. Serena barely even knew her yet she had gone through all of this trouble.

"Thank you so much." Dawn said sweetly. "Believe me, I'm totally fine now."

"I'm happy to hear that. Ash was beating himself up for not keeping track of you last night." Serena added. "Actually, that's also why I stopped by. I wanted to talk to you about Ash."

"Really?"


The Berlitz Estate was very large, much too big for the four occupants to use effectively. However, there was one room that was used exclusively by just one person - the head of the household Mr. Berlitz. It was a den in the far wing of the estate, and neither his wife nor his daughter had ever set foot in this room.

Standing alone in this den, Darach looked around the dimly lit room that was filled with priceless antique furniture and various shelves and cabinets lined up against the walls. This room was an information hub.

Darach understood that Mr. Berlitz was a powerful man, more powerful than his family knew. He had a monopoly on the shipping industry in Vermilion City, possessing full control of the shipping yards within the city. With this, Mr. Berlitz had a wealth of connections around the city to all sorts of important figures. These sorts of connections came with secrets though, all of which were contained within this den.

'Ash Ketchum.' Darach said as he approached one of the cabinets. Opening it up, he began to flip through the files contained within it.

Darach didn't venture into this den often, but when he did it came with a good reason. Dawn's mention of the surname 'Ketchum' sounded oddly familiar. He had heard it somewhere before, although he didn't think that it would be associated with a high schooler, one that Dawn of all people would know.

"Ah, here it is." Darach noted softly as he pulled out the file he was searching for that was labeled with the name Ketchum. Heading over to the nearby desk, Darach laid it down, opened it, and was instantly taken aback by its contents. The first document within it was a police investigation concerning the murder of Delia Ketchum.

Beginning to move through the contents of the file now, Darach was quite surprised by what he was learning. Briefly, it touched on each of the members of the Ketchum family, Aaron, Delia, and Ash. However, the bulk of its contents surrounded the business agreements between Mr. Berlitz and Aaron Ketchum, the husband, and father. The two of them had formed a partnership almost twenty years ago.

Mr. Berlitz had just finished constructing the last extension of his shipping yards, deeming his project complete. Many of his associates advised that he hire some sort of security to ensure that his yards didn't attract unwanted attention. Mr. Berlitz had hired two other security agencies, both of which failed to prevent Pokemon trainers from using his shipping yards as an area to host battles. So he turned to Aaron who was running a business off the books, using Pokemon trainers for security detail.

This worked like a charm, allowing his shipping yards to thrive with there being no threats to his business. However, tensions between Aaron and Mr. Berlitz began to spark over the course of a few years until the fuse was finally lit. Within a short period of time, the tensions between both parties went off like a bomb.

Delia was killed.

Aaron disappeared.

Little Ash was orphaned.

The whereabouts of Ash and Aaron were unknown since the information had been left unattended for years now.

'Hmm, this could be useful.' Darach noted.


Dawn was seated in the passenger seat of Serena's small car as they raced along the expressway that would take them to the north side of Vermilion City. Their conversation earlier had been very short as Serena simply grabbed her by the wrist and dragged her into her car so that she could take her across town. Fortunately, Dawn had been dressed decently so she didn't protest as Serena practically kidnapped her.

"So do you remember last night when Miette asked you if you like Ash?" Serena asked her.

"Yeah, why do you ask?" Dawn asked slowly, eyeing the brunette as she drove.

"Well, I just think that you should know that if you plan on getting close with Ash, there are a few things you might want to know." Serena explained with a very sobering tone. Dawn could tell that this subject was going to be heavy.

"I mean, I think I got the gist of it last night. I never would've guessed that Ash wanted to become a Pokemon trainer." Dawn commented. She was still in shock over this discovery, struggling to wrap her head around how Ash could be interested in Pokemon. It didn't make any sense to her at all. "He's such a good artist too. Why would he want to become a Pokemon trainer?"

"Ash has uh…a complicated life." Serena said with a sigh. "To him, becoming a trainer is sort of a quick fix for it."

"But you could get arrested for being a Pokemon trainer." Dawn stated, shaking her head a bit. She genuinely wanted to know why such a talented person like Ash would turn to such a dangerous lifestyle in search of stability. It didn't make any sense.

"He knows that. It's not enough to stop him though."

"That's just a waste of time then." Dawn proclaimed.

"Watch it, Dawn." Serena said sharply, her expression darkening momentarily.

Dawn was taken aback by Serena's change in tone. Realizing that she must have overstepped her boundaries, Dawn remained silent, waiting for Serena to continue speaking.

"Sorry. It's just that I know he has a lot on his plate right now, but he's always working hard. So please, don't say things like that." Serena said defensively.

Dawn remembered Ash's criticism of her, that she only took everything at face value. At this very moment, she was sitting in an opportunity to break free of this habit, all she had to do was pay closer attention to what Serena had just shared with her.

Dawn could discern from Serena's comment that she knew more about Ash than she let on.

"Don't get me wrong though Dawn, I hate what he's trying to do." Serena continued, slightly irritated now.

"You don't want him to become a trainer?" Dawn asked softly.

"None of us do-" Serena stated firmly. "-with the exception of Brock."

Dawn furrowed her brow at the thought of Brock encouraging Ash to become a Pokemon trainer.

"Why would Brock do that?" Dawn asked with a furrowed brow.

"The two of them knew each other before I even met Ash. So I probably don't know any better than you." Serena admitted.

"So then, what do you know about Ash?" Dawn asked curiously. It was clear Serena knew him better than she did.

"Ash is…this amazing person that's been stuck for…I don't know how long now." Serena responded.

"Stuck?"

"Yeah, like you've seen what he's capable of. He used to dance with our group, and I've seen some of those paintings in his house. He's incredible! But he can't build on any of it." Serena lowered her voice with her last statement, appearing to be disheartened by what she was saying. Dawn could tell that Serena wanted Ash to succeed, and his choices were bothering her.

"So what's the reason he wants to become a Pokemon trainer?" Dawn asked once again, returning to the root of this problem.

"It might be easier if I just show you."


Dawn now stood on the front porch steps for a two-story building with Serena at her side. The brunette had taken her into a dense neighborhood on the north end of Vermilion City. There were people everywhere enjoying their Saturday morning since there was no work or school. However, the two girls remained focused squarely on the house in front of them.

"So what are we doing here?" Dawn asked, causing Serena to sigh deeply.

"Sorry, it's been a while since I've been here." Serena replied as she raised her hand, beginning to knock on the door.

It was a few moments before the door opened up, revealing a young purple haired girl and an older woman with golden hair. The two of them gasped at the sight of Serena, their eyes wide.

"No way, Serena?!" They exclaimed together, causing her to laugh.

"It's good to see you guys too." She said, greeting Casey and Cassidy who invited them in.

"Macy, guess who's here?!" Casey shouted as she ran upstairs to retrieve her younger sister.

"And who might you be?" Cassidy asked after closing the door, placing her gaze on Dawn.

"This is a friend of Ash's. Her name is Dawn. Dawn this is Cassidy, Ash's…" Serena trailed off in search of a title that she could give to Cassidy.

"Caretaker." Cassidy interjected, getting a nod of thanks from Serena.

"So this is where Ash lives?" Dawn asked as she looked around their home.

"You got it." Cassidy said she motioned for them to come with her.

"Is Ash here right now?" Serena asked tentatively.

"No, he went out earlier this morning. He'll be back later if you wanted to see him." Cassidy said as they entered the living room, allowing Dawn to see one of the murals Ash had painted in the house.

"Oh my gosh!" Dawn exclaimed as she stared at the massive painting. "Who did this?!"

"Ash of course," Serena said, causing Dawn's jaw to drop. "I thought you would've figured that out yourself Dawn since you're always going on about how he's such a great artist."

"Well I mean I've only seen his sketches. I had no idea he could paint like this!" Dawn explained, motioning to the mural.

"Serena!" Dawn turned to see a small girl come running down the staircase beside them gleefully having spotted Serena. Reaching the bottom of the stairs, she turned and raced at Serena, latching onto her leg. Looking up, she noticed that Serena's hair was much shorter than the last time she had visited. "Aww, you cut your hair. I like it better long."

"Oh I'm sorry Macy. I just felt like it was time I did something different." Serena replied as she kneeled down to collect Macy from the floor.

"So what made you stop by today?" Cassidy asked as leaned over the banister of the staircase, listening to their conversation.

"Dawn has gotten to know a bit about Ash since she first met him," Serena explained, gesturing toward the bluenette. "I thought she might want to be well informed about a few things going in."

Cassidy now turned to Dawn, taking a few moments to quietly observe the girl. Then she nodded to Serena who left with Macy, heading toward the kitchen. Cassidy then looked up at Casey and motioned for her to get moving. She didn't want her listening in to their conversation. With a huff Casey went back upstairs, leaving Dawn and Cassidy to speak privately within the living room.

"Boy, it's been a long time since Serena came by," Cassidy noted with a smile. "It must still be tough for her to come here by herself."

"Why would it be tough? All of you seem to like her." Dawn pointed out, recalling how they had greeted her at the door.

"Well, she and Ash used to date." Cassidy revealed, surprising Dawn.

"Really?" She exclaimed, receiving a nod from Cassidy.

"They were good for each other too. Serena's older than him, so it was easier for her to get through Ash's thick skull." Cassidy commented with a chuckle.

"They used to date. So what happened, if you don't mind me asking?" Dawn inquired now, causing Cassidy to go take a seat on one of the sofas, inviting Dawn to join her. Once the two of them were seated and comfortable, Cassidy began to speak again.

"My big mouth is what happened. I revealed some things that were better left in the dark, and it broke them apart." Cassidy explained, and Dawn donned an expression of concern.

"So then, what are you going to tell me?" Dawn asked. If a conversation with Cassidy ruined the relationship between Ash and Serena, why would Serena bring her here to talk to Cassidy?

"Obviously I've learned my lesson, Dawn. I just didn't anticipate Ash reacting like how he did." Cassidy explained, motioning for Dawn to remain calm. "However, there are some things about Ash that you need to know."

"I already know he's trying to become a Pokemon trainer. I don't know why he wants to be a trainer, and Serena didn't really give me a straight answer about it either." Dawn said, and Cassidy began to nod to herself a bit.

"So Dawn, can you answer this for me? What do you feel toward Ash?" Cassidy asked her in a solemn tone. Cassidy wasn't beating around the bush; she got straight to the point.

Dawn had been asked a similar question last night. Serena had also asked her a similar question on the ride here. Did she like Ash? Dawn still didn't have a definite answer.

She had seen two sides of Ash Ketchum since meeting him. One that was reserved, quiet and observant…the version of him that she had spent a week with at school. Then there was the person that she had met last night. The person that smiled vibrantly around his friends, who danced like a goofball, that passionately stood beside anyone that he cared about. The person that had come to her rescue once again last night. Dawn was certain that this was the person that she…'liked.'

"Yes. I do like him." Dawn stated, her voice possessing clarity. Cassidy furrowed her brow, giving Dawn a look of uncertainty. Peering into Dawn's blue eyes, she searched for any doubt within them, but Dawn's eyes were unwavering.

"Dawn…I don't mean to sound rude when I ask you this, but are you sure you're prepared for this?" Cassidy asked her.

"I don't know what it is you're going to tell me, but it won't change my opinion of Ash," Dawn stated firmly. "I've seen enough of him myself to know that he's a good person."

Cassidy's expression brightened a bit at Dawn's response. It was similar to what Serena had said when she and Cassidy had this discussion some time ago.

"So can you tell me what's so complicated about Ash?"

Cassidy leaned back into the sofa for a moment, admiring the stance Dawn had taken for Ash. Dawn hadn't known Ash for long, but it was clear that he had left a lasting impression on her already. Perhaps she might be able to trust Dawn.

"He's caught between two worlds right now." Cassidy revealed.

"What worlds?" Dawn asked as she leaned toward Cassidy a little.

"You've seen how talented he is," Cassidy said, looking back at the mural beside them. "There's so much he could do with himself, but he wants to be a Pokemon trainer. He's a senior in high school right now. He should be enjoying himself, spending time with his friends, and getting ready to take his next step in life."

Cassidy sighed deeply though, taking a few moments before she continued.

"Instead of doing things like that, he goes to work after school. And if he's not working, then he's out there somewhere practicing to become a trainer." Cassidy revealed causing Dawn to frown slightly, a look of apprehension forming on her face.

"But why though? Why is he trying to become a trainer?" She asked, making eye contact with Cassidy once again. The older woman was a bit surprised by the honest concern Dawn had for Ash. Clearly, Ash had carved a little place in Dawn's heart.

"There are a lot of reasons…but I feel like the biggest reason is to help me. If it weren't for Ash, we probably wouldn't be living here." Cassidy admitted, shaking her head a bit. "Originally my husband had bought this place, but one thing led to another and now I'm the owner. Unfortunately, I don't have any income. We get a bit of support that covers our necessities, but Ash handles everything else."

"I don't understand. You said you're his caretaker, why aren't his parents doing anything?" Dawn asked, causing Cassidy to suck in her lower lip for a moment.

"His father disappeared…and his mother passed away a long time ago." Cassidy responded, and the mood in the room became somber.

"Oh…" Dawn looked down now. "So then, he's all alone."

"No, I wouldn't say that," Cassidy said immediately. "He has us."

Cassidy motioned to herself, and then to the corridor where they had previously been standing as a reference to the two younger girls.

"They may not be his sisters, and I may not be his mother, but you wouldn't know that based on the way he treats us." Cassidy declared. "He would work himself to death to keep us all together."

"So then…" Dawn paused for a moment, wondering if she should press further with her next question, or if it might have been too rude. Cassidy was a blonde, yet Casey had purple hair, and Macy was a brunette. They bore no resemblance to Cassidy, at least far as Dawn could see, so that left her to wonder… "Are those girls orphans as well?"

Cassidy nodded.

"They were orphaned when they were young," Cassidy replied with a sorrowful smile. "I took them into my care because…I guess you could say I'm trying to atone for some of my past mistakes."

"You're amazing," Dawn said suddenly, surprising Cassidy. "To just take them into your home and sacrifice everything for them. That's incredible."

Cassidy's cheeks reddened at the compliment. It wasn't often she was praised for the choices that she had made, but she was grateful that Dawn understood.

"So Ash is trying to become a Pokemon trainer for…the money? Is that what he's after?" Dawn inquired now. She wasn't aware of how trainers made their money, but from what she had seen in the news, these gangs or 'kingdoms' as Brock put it, do have some sort of income to provide for so many trainers.

"More or less, that's what he wants."

"He's an amazing artist though. Hasn't he tried to sell his art?" Dawn asked incredulously. Cassidy opened her mouth but hesitated to speak for a few moments as she worded her answer.

"He has tried. I remember he had approached a few directors about getting some of his work into a gallery. They turned him down." Cassidy stated, and Dawn's expression softened. "They were looking for artists with a…a body of work. Ash is unknown, and he told me that at his age, it'll take him years before anyone will acknowledge him."

Dawn leaned back into her seat. She understood what Ash was talking about. It wasn't easy to become a recognized artist during your youth, especially in Vermilion City which was known as a hub for the arts.

"What if I helped you all out?" Dawn asked and her expression brightened with this offer. "My dad makes a lot of money. What if he gave you some to help out around here, to make things easier?"

"We're not some charity case Dawn," Cassidy stated, and Dawn sunk into her seat at that. Cassidy pursed her lips, realizing she could have worded that a bit better. "I mean, believe me, Dawn, I'm incredibly touched that you would be willing to do such a thing for us. But I couldn't accept, we couldn't accept. Ash wouldn't be happy about it. He's so hard-headed and stubborn. He doesn't know how to ask for help, even when he needs it."

Dawn crossed her arms in front of her chest with a huff. For everything that she had learned about Ash Ketchum since she had met him, Dawn never would've imagined that he was stubborn or hard headed. However, she did find this thought cute and amusing.

"You know Dawn, I'm glad you respect Ash's ability as an artist. You're an artist too, right?" Cassidy asked, causing Dawn to perk up. The bluenette gave her an energetic nod. "Ash lost his confidence when that gallery rejected him, and since then he's been more focused on becoming a trainer. I'm not much of an artist, so my opinion doesn't matter much to him, but I feel like if other artists reminded him of how good he is, he might stop pursuing Pokemon training so much."

Dawn nodded slowly at this, realizing why Serena had brought her here.

"…I've seen some of those paintings in his house. He's incredible! But he can't build on any of it."

Serena understood everything that Ash was capable of. She could see that he was wasting his talents trying to become a Pokemon trainer. Dawn felt a sense of admiration for what Ash was trying to do, but she found herself agreeing with both Serena and Cassidy. Ash didn't need to become a Pokemon trainer in an attempt to solidify his life. He could do almost anything he wanted, and he was bound to find success! Cassidy knew that. Serena knew that.

Speaking of Serena…

"So what exactly made Ash and Serena break up then?" Dawn asked curiously, recalling that Cassidy had mentioned this to her earlier.

"There are other reasons Ash is trying to become a Pokemon trainer, and I shared them with Serena. She only has Ash's best interests at heart, but he didn't appreciate her trying to change his goals. This strained their relationship, and eventually, they broke it off." Cassidy explained. "I don't want the same thing to happen to someone else."

Dawn was taken aback when Cassidy suddenly took hold of both her hands as if to plead with her.

"That's why I'm making a different request for you Dawn. I want you to remind Ash of his true talents." Cassidy continued. "Becoming a Pokemon trainer is going to take him down a dark path, and if he commits to it, he won't turn back. So please, help him to see that there are other things that he can do with himself."


Monday, September 12th

"Hey, Dawn!" May called out to her friend as she pursued her through one of the corridors of the school. Dawn glanced back, containing her urge to giggle at May's willingness to shout over the chatter of the other students, who had all turned to look at her now. Dawn stepped off to the side, allowing the people being her to proceed as she waiting for May.

"What's going on, May?" Dawn asked once her friend was walking alongside her.

"The real question is what's going on with you? I was texting you all day Saturday and you didn't respond to any of them." May pointed out as she gave Dawn a suspect glance.

"Oh gosh, I was really busy May." Dawn explained as she pulled out her phone to check her message history. She hadn't looked at her phone at all over the weekend, and just as May had said there was a one-sided conversation from May that was completely unanswered. "I'm so sorry May!"

"I was beginning to think you didn't want to hang out with me anymore since you've been spending all of your time with Ash lately." May pointed out with a smirk, causing Dawn's cheeks to flush red.

"I have not!" Dawn protested.

"Oh really, so do you want a ride home with me after seventh period?" May asked with a twinkle in her eyes. She knew Dawn had spent every day last week with Ash in Ms. Fantina's room during eighth and ninth period.

"Uh well, I can't." Dawn said weakly, causing May to put a hand to ear as she leaned closer to Dawn.

"And why's that Dawn?" The brunette pressed.

"Cause I'll be…" Dawn trailed off before a thought crossed her mind that would allow her to change the subject for at least a few moments. "Wait for a second, I thought your parents took your car from you."

May quickly pulled her keys out of the side pocket of her backpack, flashing Dawn a grin of pride as her keys jingled.

"I'm the best daughter ever, so they gave it back to me," May responded before dropping her smile. She wasn't going to let Dawn get away. "But that's beside the point Dawn. Don't you want to accompany me for a little ride after seventh period?"

Unable to think of anything else to deter May's curiosity, Dawn gave in an admitted that she had been spending that extra time with Ash and riding him with him on the bus.

"I see, so you're dumping me for him huh?" May asked her playfully.

"May! You know I wouldn't do that." Dawn proclaimed.

"But I've been so lonely Dawn. I was away for the whole summer, and now that I'm back we haven't spent any time together outside of school." May pointed out as clasped her hands together, placing them over her chest. "I don't know how much more of this my heart can take."

Dawn rolled her eyes at May's antics, but she could understand her dear friend's point of view. They were only talking to each other at school.

"Okay, okay. I'll make it up to you then. This weekend we'll go out, girls only." Dawn suggested, earning a wide smile from May.

"I'm going to hold you to it," May said before giving Dawn a sly glance. "So now let's get down to business."

Dawn furrowed her brow as she looked at May.

"What did you do with Ash this weekend?"

Dawn's face became red at May's question.

"How did you know I went out with Ash?" Dawn exclaimed.

"Actually, I didn't. But you just confirmed it for me." May said, sticking out her tongue at Dawn. She pursed her lips, averting her gaze from May.

"You're the worst." Dawn commented, and May snickered in response.

"I love you too Dawn," May replied, giving Dawn a few moments to settle down. "So what did you guys do?"

"He took me to this little party that's all." Dawn replied, causing May to lean over toward her with a look of suspicion. Dawn continued to avoid eye contact with May, knowing full well what she had said wouldn't satisfy May's curiosity.

"That's it?" May asked, wrinkling her nose. Dawn nodded. "I don't know~, it sounds like your leaving out the juicy stuff."

"Nope, that's the whole story." Dawn stated as she looked at May once again. May frowned after studying Dawn's expression. She couldn't find any hints that Dawn was hiding something. May couldn't accept this though. She knew Dawn barely went out, mainly because of the curfew her parents had set, and there was no way Dawn could be this calm about her first party.

"Okay then…did you have a good time with Ash?" May asked her, and Dawn seemed to think about the answer for a few moments.

"Yeah…I did." Dawn said, nodding softly.

"So um, are you serious about him?" May inquired, and she raised her eyebrows at Dawn's quick reply.

"Yup. I really want to get to know him better." She said sternly, and May smiled at her.

"So you can get home on your own today?" May asked her, changing the subject suddenly.

"Uh yeah. I'm taking the bus."

"With Ash?"

"Not today, he has to get to work early." Dawn explained, noticing a twinkle in May's eyes before she darted off. Dawn tilted her head with a sigh as she watched May go, waving to her before she disappeared into the traffic of the halls.


May was seated behind the steering wheel of her sporty bright blue car that she had received from her parents. Resting on her nose was a pair of wide aviators as she drummed on the wheel to the beat of the song she was listening to. She was parked beside the field behind the school which was across the street from the school itself. Rather than having students struggle to cross the bustling streets of Vermilion City to get to this field, they built a bridge over the roadway to avoid any accidents.

This field was also the location of the bus stop that Ash and Dawn used to catch a ride over to the part of town Dawn lived in. Dawn had told her that she and Ash would be taking different buses today, so May's intention was to meet with Ash on her own.

May still didn't quite understand what it was Dawn saw in Ash. The only thing noteworthy, to her at least, was how well he could draw. Outside of that, he didn't really stand out. He wasn't a smiley person, he wasn't talkative or outgoing, or even that interesting. Yet Dawn was absolutely obsessed with him, going as far as to reject an afternoon at their favorite café together. There had to be something else about him, something that May would have to find on her own.

Leaning forward in her seat, May peeked over her sunglasses as she spotted Ash and Dawn exiting the small stairwell that connected to the bridge. They were chatting as they approached the pair of benches beside the bus stop. May couldn't help but notice how animated Dawn was as she spoke to Ash, and to May's surprise, Ash was almost matching it. They sat down on a bench, and May leaned back into her seat now as she watched them converse. It would be a few minutes before the first bus arrived, and May felt her heart jump into her throat as she realized she didn't know which of the two of them would be leaving first. All of this waiting would have been for nothing if Ash got on this bus.

Fortunately, May could breathe a sigh of relief as Dawn got onto this bus, leaving Ash alone at the bus stop. Knowing that she couldn't waste a moment now, May threw her car into gear and backed out of her spot. Swinging out of the parking lot, she turned onto the road and then pulled up onto the shoulder alongside the bus stop. Ash looked up curiously at her now, his brow furrowed and his confusion only seemed to intensify as May rolled down the window on the passenger side for him to see her.

"Hey." May called out to him after lowering the music, motioning for him to approach her car.

"Hey?" Ash replied slowly as he stood up and came over. He couldn't think of a reason for May to approach him like this, nor did he know much about the brunette. The two of them had only spoken on a few occasions and exchanged just a few words. Dawn had always been present, so this was the first time that he had ever spoken to May without Dawn with her.

"I heard you need a ride." May began as she unlocked the doors, motioning for him to get in. Ash looked at her funny and then opened his mouth to respond, but May immediately interjected with a - "Dawn told me."

Ash lowered his shoulders and tilted his head.

"Are you sure?" He asked.

"Yeah, don't think anything of it." May said happily as he opened up the door and slid into the passenger seat.

"Did she give you a reason?" Ash pressed as he glanced at May who had been watching him closely. She lowered her aviators, revealing how intently she had been following his movements, examining everything about him.

"No, she didn't." May replied, refusing to break her gaze on Ash. This left him unsettled as he shifted in his seat. Pulling his seatbelt across his torso, Ash waited for her to start driving now, but May continued to stare at him. Then she leaned closer, causing him to straighten up uncomfortably, unable to figure out exactly what may was trying to do.

May was a little confused now. It was like Ash had gone back into a shell or something. Just a few minutes ago he had been holding a conversation where he was so bright. Now his reserved demeanor had set back as his expression remained neutral.

"Uh, is there something you want May?" Ash asked her tentatively, causing her to sigh exasperatedly before she returned her focus to the road.

"You know what Ash, I'm just going to be upfront with you. I want to get to know you better." May stated, leaving Ash dumbfounded.

"Um, why?"

"Does a girl need a reason?" She asked with a huff, looking at him expectantly.

"No…I was just curious is all." Ash replied immediately.

"So you don't mind then?"

"Well, I don't really think I'm in a position to refuse." Ash noted with a small chuckle, scratching the back of his neck. He was in her car, after all, accepting a free ride to his job.

"Okay, so I've known Dawn for a long time and she's an artist like you. She's got this whole, 'creative process.' I call it, being weird. Anyway, since you're obviously a good artist, I just wanted to know what you were like…like if you're similar to Dawn." May explained to him, and Ash put on another funny expression.

"So you want to know if I'm…weird?" Ash asked her. May opened her mouth to speak but froze upon realizing that she had talked herself into a corner. She didn't intend to lump him together with Dawn as 'being weird' as she put it, but Ash didn't seem to take any offense from her comment.

"Uh, yeah. Let's go with that." May said sheepishly, trying to laugh it off.

For a faint moment, May saw the corner of his lips curve upward as he snorted.

"Okay, so what do you want to know about me?" He asked as May took her foot off the brake and joined the traffic.

"Let's start with something easy. Where do you work?" May asked him.

"At Wallace's Craft store. It's this artsy little store uptown." Ash replied and May blew a raspberry.

"Figures you'd be working at an art store," May commented before a light bulb went off in her head. "So then, who taught you how to draw?"

Ash's expression darkened momentarily, although this went unnoticed by May's whose eyes were locked on the road.

"My mom taught me when I was little." He stated.

"Oh, so she was an artist or painter or something?"

"Um, not really. She just told me that her family had always been on the creative side. She says I inherited that from her." Ash explained, earning a nod from May.

"Cool." She said, moving on to her next question. "So~, what about nicknames? Do you have any?"

"Nothing serious really. I mean, there's a little someone I know that calls me Ashy, but no one has ever really given me a nickname." Ash responded.

"Lame," May stated, sticking her tongue out a bit. "Next question. Who knows you the best?"

"What do you mean?"

"Come on Ash, you're not some kind of hermit are you?" May said with a giggle. "It has to be your mom or dad, or maybe a sibling right?"

Ash chewed on his lower lip for a moment, gazing out the window.

"Actually, there is a lady who's raised me since I was young. Her name's Cassidy and I think it's fair to say she knows me pretty well." Ash explained.

"Oh, so she's like your nanny?"

"Yeah, if you want to call her that." He said with a nod.

"Alright then, do you have any siblings?" May went on, building on the subject of family since they had touched it.

"…Yeah." Ash said. His sisters may not have been related to him by blood, but he had known Casey since she was four, and had known Macy from the tender age of just nine months. The bond he shared with them was more than close enough for him to consider them his siblings.

"How many?" May went on.

"Two. Sisters actually."

"Do you have a favorite?" May asked with a small grin. Ash stopped to think about each of the girls.

He had known Casey for much longer, almost eight years. She had always been a handful throughout her childhood, and as she entered her teenage years Ash could only imagine how things would go from there. She was always very spirited and lively, always eager to act on her own at the drop of a hat. Ash admired how independent she wanted to be while she was so young.

Macy, on the other hand, was still so young and impressionable. She was only four after all. Sweet and innocent. She was like a ray of sunshine, forcing everyone around her to relax and smile no matter what was on her mind. Ash shook his head with a smile.

"I don't have a favorite." He stated.

"Oh please. I'm sure one of them must get on your nerves from time to time." May pointed out, recalling how often her younger brother would annoy her.

"Nope, they're both wonderful."

"Then I bet your parents have a favorite. They always spoil the youngest one after all." May said, speaking from experience. "If there are three of you I bet your youngest sister must be spoiled rotten."

Ash clenched his right hand into a tight fist, keeping a deep frown hidden from May.

-X-X-

Ash stood beside Cassidy within the moderately sized kitchen of their home, leaning on the counter as he watched Casey and Macy at the table, devouring their breakfast. Ash couldn't help but snort at the sight of Macy with syrup all over her mouth as she attacked what remained of her pancake.

"Here is your breakfast, Ash." Cassidy said as she lifted her small pan, sliding the pancake onto the empty plate beside him. "We're going to be eating light this week."

Ash shrugged his shoulders in reply. This was nothing new for them. There were good weeks and bad weeks. Although the latter meant that they would be stretching out their meals.

"Can I have some more?" Macy asked as she looked over at Cassidy. The blonde woman raised her eyebrows for a moment before she turned her back to Macy, beginning to scan the counter for something that she could use to subdue Macy's appetite.

"I don't know sweetie." Cassidy mumbled.

Ash spent a moment watching Cassidy search for something she could give to Macy, and then he picked up his plate and approached the table where the two girls were seated. Tilting his plate, Ash plopped his pancake onto Macy's plate causing her eyes to brighten considerably as she looked up at him.

"Thanks, Ashy!" She exclaimed, watching as he took her knife and fork.

"Don't forget to share with your sister." Ash stated as he cut it in half. He cut Macy's portion up for her, and took the remaining half and placed it on Casey's plate. She looked up at him, a bit of uncertainty in her eyes. Ash merely winked at her in response.

Stepping back from the two, Ash felt his lips curve upward as they continued to eat. Out of the corner of his eyes though, he caught sight of Cassidy who was looking at him with a frown.

"Ash." She said in a low voice, motioning for him to come over to her with a small nod. "What are you going to eat?"

"I'll figure something out," Ash replied as he glanced back at the two girls. Macy ate without a care in the world, which was more than enough to put Ash at ease. "Don't worry, I'll be fine."

-X-X-

Macy and Casey had endured so much already, some of it unknowingly. There was a lot about their lives that they were unaware of and probably wouldn't understand. So Ash wanted nothing more than to spoil both of them rotten if he was given the chance.

"Ash?" May asked, snapping him out of his thoughts. "Is something wrong?"

Ash blinked a few times, realizing that they had stopped at a red light. Looking at May, he could see that she had taken off her sunglasses to look at him directly. Ash licked his lips, noticing that they had become dry. How long had he gone silent for?

"I'm sorry, was I being insensitive?" May asked, but Ash shook his head. After posing her last question to Ash, May had assumed he was thinking deeply about his answer. She left him in his thoughts for a bit, but the silence had left her a little unnerved until she decided to check on him. "Did I say something to upset you?"

"No, you didn't." Ash said quickly, assuring her that he was alright.

"Okay then…why don't we change our focus? Ask me a few questions." May insisted, and after a few moments, Ash agreed. After taking some time to think of a few questions for the brunette beside him, Ash asked his first question.

"Alright May, what do you like to do with your free time?"

It was a simple question, and May gave a…not so simple answer. For all of the time he had spent around May and Dawn, he never would've guessed that May could turn into a total chatterbox. She shared everything with him, rambling endlessly. Walks on the beach. Tennis matches. Karaoke. Watching movies. The whole nine yards. Ash could plan an itinerary for a vacation just using May's hobbies.

"And I tried water skiing just once but that was a disaster so I don't really recommend it to people." May stopped to take a breath, and out of fear of her continuing Ash interrupted her.

"Okay May." He interjected. "How about we move on to the next question?"

"I still had a little more to say for the last one, but I guess we can move on," May replied, smiling a bit. Ash lowered his shoulders, sighing inwardly with relief. "Ask away Ash."

"Where do you see yourself in…five years?" Ash asked her, and this one kept May quiet for a little while.

"You know," She began after a long pause. "I've never really given this much thought. I just always figured that things would just fall into place around me."

Ash wrinkled his forehead, confused with her answer.

"So…you don't see yourself doing anything in the future?" Ash reworded his question for her.

"No I mean, I just stopped thinking about the future since uh…" May stopped briefly, frowning a bit. "Anyway, I really haven't bothered trying to plan something out. I just see myself having fun."

"There's more to life than just having fun ya know." Ash pointed out.

May remained silent now as gathered her thoughts. For the past couple of years, she had only been looking to have a good time. She never gave anything else much thought.

"Isn't there something that you really want?" Ash continued as he waited for her answer.

Her parents were well off, so she got anything she wanted. She could do anything she wanted. There was no work required. She had a car on her sixteenth birthday and she didn't even ask for it, not that she would turn down this gift from her parents. May never really had to work for anything.

A certain green-haired young man flashed in her mind for a moment. The only thing she wanted and didn't have. Drew. She had been trying to win his attention for the longest time now, but as she thought about it now, she had barely put in any real effort. It had been dumb luck that she got to spend some time with him during their summer vacation.

"Yeah, there is something I'd like to get," May noted softly. "There's a guy I've been interested in for a while now, but I've never really done anything on my own to get his attention."

"What, are you waiting for him to make the first move?" Ash inquired curiously. He understood that normally guys would make the first move, but in this case, he couldn't see why May was hesitating.

"Er, well we kind of sorta went on a date over summer vacation. He hasn't talked to me since though, so I just kind of thought he'd come and talk to me eventually." May replied nervously, and Ash was dumbfounded for a moment.

"Sometimes May…you have to take the initiative and be the gutsy person who makes the first move. At the very least you won't regret letting him slip away while you did nothing." Ash said to her, and those words seem to resonate within May.

Living without regrets….

But wouldn't it be better to save herself the heartache of rejection, or the disappointment of a failed relationship?

"I…don't want to get hurt." May admitted after a little while. Ash shrugged his shoulders as he looked at May solemnly.

"None of us want to May. It's just that, there's no way to avoid it really. At some point, all of us are going to fall and get hurt, but the only option you have is to pick yourself back up and keep moving. It's as simple as that." Ash said, causing May to glance at him for just a moment. Time seemed to slow down for her as she took this glance at Ash. He was smiling, not a big smile by any means, but it was like he was sparkling. This was the first time the two of them had really spoken to each other, and yet she could feel the warmth and reassurance within Ash's expression. She knew for sure that he wanted her to find success.

It was then that May understood what Dawn must have been seeing in Ash. Even if it was for but a brief moment, she finally found the person that had so effortlessly captured Dawn's attention. It was a young man who was capable of pushing you to better yourself. Of course, someone as ambitious as Dawn would be attracted to him.

Setting her sights on the road again, May felt a smile creeping up on her face and a fire in her heart.

"Thanks, Ash. There's something I have to do once I drop you off." May stated, earning a smile from Ash as he gave her a nod. "And if you ever want to talk, I'm always here."

"Oh, that's awfully nice of you May. I really appreciate that." He said kindly to her.


Feeling the bus come to a halt, Dawn blinked several times as she looked out the window to check her surroundings. She breathed a sigh of relief that she was still about ten minutes from her stop. Looking back down at her lap, she saw that her sketchbook was resting there and the page was still blank despite how much time she had spent on the bus already.

Normally she had no trouble spending the entire bus ride sketching, but today she was distracted with many, many thoughts concerning none other than Ash Ketchum.

Everything that Cassidy had shared with her on Saturday was fresh on her mind. Prior to meeting that woman, she had no idea that Ash was an orphan or what his living situation was like. Biting down on her lower lip a bit, Dawn couldn't help but feel a touch of guilt in her chest for all of the times she had asked Ash to accompany her to her luxurious home. Might he have thought that she was flaunting her lifestyle at him?

Dawn shook her head a bit, tossing that thought out of her mind. Ash didn't seem like the type of person to get irritated over something like that. However, Dawn felt terrible for bothering him so much since they had first met. All that time he had spent showing her the bus route, the money he spent on round trips around the city. On the other hand, she never would've seen the real Ash Ketchum had she not gone out of her way to get to know him.

After talking to Cassidy though, Dawn felt as though she was caught between a rock and a hard place. She liked Ash, but with everything she had learned, there were so many questions on her mind about supporting him. He wanted to become a Pokemon trainer of all things, and his friends and family didn't want him to have any part in that.

"Don't get me wrong though Dawn, I hate what he's trying to do."

"Becoming a Pokemon trainer is going to take him down a dark path, and if he commits to it, he won't turn back. So please, help him to see that there are other things that he can do with himself."

So what was the right choice here? It was dangerous, not to mention illegal, to train and use Pokemon so she could understand the sentiments of everyone who didn't approve of Ash's goal. Dawn wouldn't dare call his dream stupid or illogical, but Ash wasn't doing himself any favors aiming to be a Pokemon trainer. There was just so much to consider!

Dawn exhaled loudly, and then her eyes widen as she realized there were other people seated around her, most of which had taken a glance at her now. Blushing a bit, she tried to laugh it off before hitting herself mentally.

"Next stop, Diglett's Boulevard." The driver called out, and Dawn began to gather her belongings.

She would figure out what to do…hopefully.


Tuesday, September 13th

"Good mor~ning Dawn!" May said cheerfully, greeting her friend as she took her usual seat beside Dawn in their first period art class. Dawn wasn't surprised by May's energy despite how early it was in the morning, but the tremendous grin on May's face left Dawn wondering what had the brunette in such a good mood.

"Well, aren't you cheery today. Did something good happen?" Dawn asked her.

"You got that right." She said before glancing over her shoulder to take a look at the raven haired boy in the back of the class. As always he was focused on another one of his sketches, paying no mind to anyone around him. "And you could say it was thanks to Ash."

Now May had Dawn's full attention.

"Huh?" She almost exclaimed. "What do you mean?"

"Whoa chill Dawn, I wasn't trying to make a move on your man or anything." May said with a wink, causing Dawn's cheeks to flush red.

"May, stop saying stuff like that." Dawn whispered to her harshly as she looked around, hoping no one had heard that comment.

"Oh, so you don't want to know how I scored a date with Drew this weekend." May concluded, feigning pain as she placed a hand over her heart.

"Wait, what?" Dawn exclaimed. "How'd you do that?"

"So yesterday I decided to give Ash a lift to his job. And we just sort of talked on the way there." May explained with a small smile. "He's really down to earth and kind of insightful too."

"So how did this help you ask Drew out?" Dawn inquired, trying to put the pieces together.

"Well talking with Ash helped me put some things in perspective. He helped me to take the initiative with Drew." May went on. "I went straight to Drew's house after I dropped Ash off, and I just asked him."

"Just like that?" Dawn exclaimed, and May nodded with enthusiasm.

"Ye-up. I never would've thought it'd be that easy."

"Wow, you go May!" Dawn said, raising her hand for a high five. May only chuckled nervously though, looking away from her friend. Dawn narrowed her stare at May, her gaze becoming filled with suspicion. Whenever May laughed like that meant that there were strings attached to something. "So what exactly did you ask Drew, if you don't mind me asking?"

May pursed her lips for a moment, then she looked at Dawn and smiled.

"Well~, I sort of told him that a friend of mine was going on a date this Saturday, but she was nervous going out by herself, so I suggested we go on a double date to take some pressure off of her." May explained, and Dawn quickly realized where this was going.

"And who is this friend?" Dawn asked, crossing her arms in front of her chest.

"You." May admitted, and Dawn wasn't surprised.

"Alright May, word for word. What did you tell Drew?" Dawn demanded to know.

"I told him that my friend Dawn is interested in the new guy at school, Ash Ketchum, so she asked him out this Saturday. But she's a little nervous, so she asked me to come along. Naturally, I don't want to be a third wheel so I wanted to bring a date of my own." May said, retelling what she had said on Drew's front porch yesterday. Dawn clicked her tongue.

"You know May, you're a real piece of work."

"And that's why-you-love-me~." She said in a sing-song voice, placing her index fingers on each of her cheeks.

"You're really lucky that I do May," Dawn said, rolling her eyes. "I just want to rip out my hair now."

"What for?"

"Don't get me wrong, I really want you to go on your date with Drew, but to do that I have to ask Ash to go on a date with me." Dawn explained. "I've never asked anyone out on a date before."

"Well, you were going to ask him out eventually, weren't you? Think of this as a little nudge in the right direction." May reasoned with her, and Dawn gave the brunette a sharp glance.

"This is way more than a little nudge." Dawn muttered as she glanced back at Ash. How would she pull this off?


A/N

So this was a loaded, but a pretty laid back chapter. Hope you enjoyed it and a big thanks to all the people that have been following this story so far! We're working hard on this so the continued support is appreciated.

I think this chapter just about wraps all of the set up I had been talking about during the first five chapters. From here the pace will pick up a bit so I hope you're ready for this!

As always I have to thank my beta-reader MjrGenMatt for his amazing help! It's a blast working with him.

I won't bother saying anything else this time since it's the holiday season. See you all again in 2018!