Ash, realizing that the Ariados were likely going to use String Shot, stood up and jumped straight into the air. As he predicted, the Ariados used String Shot when he stood up. He jumped, dodging their attacks causing them to the other Ariados on the other side of Ash. Ash leaped over the tangled Ariados and ran over towards May and Torchic.

"Let's get out of here!" Ash yelled as he grabbed May and took of down the path leading towards the exit of the forest. They eventually stumbled out of the forest, exhausted from running so much.

"Well that's one way to start a day…" Said Ash, who had originally been hoping for a relaxing day.

"How did you even get here, and what happened?" Ash asked.

"Well, uh…" May started, not wanting to tell Ash cause she felt embarrassed.

"Actually, let's get back to Viridian City first. I don't wanna be this forest any longer." Ash interrupted. The two shared a laugh and returned to Viridian City, ultimately deciding to go to the city park.

They found an empty set of swings and were then finally able to relax.

"So what happened back there?" Asked Ash.

"Oh, well. I thought I'd give Pokémon battling a chance… But you can tell how that ended up." May told him, feeling completely embarrassed.

"Ah, well Virdian Forest isn't exactly the best place for new trainers to be battling, even I don't train there often." Ash replied, making May feel a little better.

" I just feel like I need something to do with Torchic, like you are with your Pokémon." May told him.

"You know May, this might sound odd coming from a Pokémon trainer, but people don't always need to do something with their Pokémon. Sure battling can help build trust and the bond between a Pokémon and its trainer, but you can do that through a variety of ways. Just being friends with Torchic can build that same kind of trust. I know someday you'll find what you really want to do together!" Ash said, trying to give May a little reassurance.

"Thanks Ash, that means a lot." May replied, realizing that she didn't have to rush her bonding with Torchic, but to let it grow naturally over time.

"That reminds me, Dawn wanted to hang out of for a bit today, wanna come along?" May asked him. Ash agreed and they left the park and headed towards Dawn's house. Ash had never seen Dawn's house, and neither had May surprisingly. May just knew the address, so they began looking for the right street. After twenty minutes of having no luck, they decided to just call Dawn so she could come find them.

Dawn told them that she'd drive over and pick them up, meeting them back at the park. Ash and May jumped when Dawn honked the horn of her car, startling them.

"Hi Dawn!" They said as they climbed into the car, before speeding off down the road.

They passed through a set of gates before driving down a long winding road, which led away from the city.

Ash and May's eyes lit up at what they saw. A large mansion and huge yard, surrounded by trees on all sides.

"Woah…" Ash said in amazement. He could only imagine ever living in house this big.

"Wait this is actually your house Dawn?" May asked, in the same state as Ash.

"Yup, home sweet home." Dawn replied nonchalantly.

"Why didn't you tell us you were, um, rich?" May asked, never thinking that Dawn would live in a place like this.

"I've learned that if you let people know that right of the bat they just will use you, but I know I can trust you guys not to say anything." Dawn explained as she parked the car into a garage beside the house.

Dawn led them through the front door of her house, causing a reaction of "oohs" and "ah's" as Ash and May took it all in.

"This place has to be worth a hundred times more than my house!" Ash said as they entered the living room. Dawn kicked off her shoes and jumped on the couch and laid down.

"It's not all that great, trust me it gets pretty boring after a while." Dawn said, causing a look of bewilderment on the others faces.

"Bored? There's so much stuff here I wouldn't be bored for the rest of my life!" Said Ash, who was scared to sit on the furniture since it looked so fancy and expensive.

"How in the world can your family afford this, it must cost a fortune?" May asked.

"Well my dad is pretty high up in a company that manufactures and sells pokeballs. It pays really well but he's always traveling, so I rarely see him. My mom has a pretty good job too." Dawn told them.

"I'm thinking of getting a job too, sitting in this house all my life has gotten really boring. You guys don't have jobs do you?"

"Well aside from Pokémon tournaments, which I've only done once, then no." Ash said.

What about you May?"

"I've never had a job, but my parents keep telling me I should get one soon." May told them.

"Why don't we all get jobs? Even better, lets all work together! Let's find someplace we can all work. Plus Ash is going to need the money if he's going to be traveling around Kanto all year." Dawn said, picturing it all in her head: The three of them working together, oh and maybe even Gary.

"That's actually not a half bad idea." May said, thinking it over.

"Sounds like fun! I say we do it!" Ash said, the other two agreeing with him.

"But we can worry about that later, I wanna see the rest of this house!" Ash said, making Dawn laugh.

1 Extensively Long House Tour Later

"And lastly here is my room." Dawn said as she pushed open the door to her room. The room was surprisingly small compared to the rest of the house, but had a nice view of the backyard, and a small balcony.

"You know Dawn, millions of people can only dream of living like you do, your so lucky!" May said.

"Your right May, but that's why I want to get a job, and eventually get my own house when I'm older, I don't want to be the lazy privileged girl my whole life. You get what I'm saying?" Dawn asked, trying not to feel like a lazy privileged girl.

"Oh ya I know what you mean, and since you brought it up how about we go out and find ourselves a job, its not like we've got anything else to do." May suggested.

"Ok lets go!" Dawn said.

The Next Week

Ash, Dawn, and May sprinted towards their lockers after the final bell rang. Tonight was their first day on the job, and afterwards was Gary's playoff soccer game. They had found a job at a local restaurant in Viridian City. Today would just be a short two or three hour orientation, just to introduce them to everything and figure out what they'd actually be doing there.

"You guys ready?" Dawn asked, who was excited for her first day.

"I don't know, I guess so." May asked, feeling nervous about never having had a job before.

"C'mon May it'll be fun! Not lets hurry before we're late!" Dawn said as they sprinted out to Dawn's car.

They arrived just in time, and met the person they'd be shadowing for the day basically. The restaurant was huge, but it also wasn't small, and there were a lot of things that had to learn and be shown. After nearly a half hour of being shown around, it was time for them to give their actual jobs a shot.

"Ok, I think I'll have all of you try being waiters first. Think you can handle it?"

The three of them nodded nervously, not sure what they were getting themselves into. First they had to change into clothes that were given to them. The girls laughed when Ash walked out, thinking that he looked funny in a suit and tie.

After nearly an hour of doing their best at being a waiter, they were finally pulled aside, done with that job for the day. They hadn't done that bad actually. Dawn was a natural, although it wasn't exactly her dream job, she didn't mind it. May hated it, unfortunately having to deal with some picky customers, and Ash did ok. He forgot a few things here and there, but didn't do half bad. It was clear that it wasn't his favorite position as he was kind of an awkward waiter.

"Ok Ash, lets have you try washing some dishes. Dawn, you can keep on with what your doing, and May, you can come with me." Their boss told them.

Another hour went by. Ash seemed to like this job, he didn't have to worry about anyone else, it was just him and the dishes. Soon enough Ash was given his schedule for the next week and was allowed to leave, shortly followed by Dawn and May. The three of them met outside by Dawn's car, before heading back to Kanto High.

"That wasn't as bad as I was expecting!" Ash said, who surprisingly enjoyed the work.

"I know right, it was actually pretty fun!" Dawn agreed. Meanwhile May sat silently in the passenger seat, who obviously had a rough first day.

"We better hurry if we want to make it before the soccer game starts!" Ash said, so they took of back towards the school.

They arrived just as the game begun, a rematch between the Dragons and the Cerulean City Seadra's, who'd beaten the Dragons just a week ago. Kanto High hadn't played several of its starters that game, so they were sure to be better in today's game.

The Dragons put a lot of pressure on the Seadra's defense right off the bat, missing a couple of good shots at a goal. It wasn't until Gary ended up with the ball that they finally succeeded.

"Gary Oak with the incredible assist to Drew for the first goal of the match! Dragons up by one!"

The crowd was extra loud tonight, cheering the team on the entire game. The first half ended with the Kanto High still up 1-0. If it weren't for them just being unlucky with some shots it would have been a blowout already.

The Dragons came out in the second half ready to fix those mistakes, and Drew scored a second goal, with another goal by Gary shortly after. The Dragons, turning the game into a blowout, dominated the rest of the game.

"That's all folks, The Kanto High Dragons have won the first round match in the playoffs! They defeat the Cerulean City Seadra's by a score of 4-0. Next Tuesday they'll match up against the #4 ranked team, the Pewter City Gravelers!" The announcer said as Kanto High advanced to just its 2nd ever semifinal match.

Typically the three of them and sometimes Gary would hang out after each game, but they were all beat from the day's work, so they all agreed that they hang out over the weekend instead.

Ash woke up early the next morning, and took Delia's car to work. Work wasn't Ash's favorite place to be on a Saturday morning, but he really was starting to enjoy it.

He spotted Dawn as he walked in, who gave him a wave as she was on her way back to her tables. Ash didn't see May anywhere, assuming that she just wasn't working today. Ash went straight to work, being so quick at his job that he often found him self day dreaming, mostly about things like owning a house like Dawn had, which boosted his motivation whenever more dishes appeared before him. Although he wasn't going to get rich by washing dishes his whole life, he started wondering about real jobs that would suit him well. Ash's plan had always been to become a professional Pokémon trainer, however that was really tough to do. As the only major payouts came from the yearly tournament in Kanto, and the top four trainers made a significant amount, enough to make a living until the next year at least. Ash had been getting lazy with his Pokémon training, not being able to fit it in with work, school, and hanging out with friends. In fact it'd been over two days since he'd seen or talked to Pikachu, who was finally starting to recover from his injury.

It was now November, and the chilly wind hit Ash and Dawn as they exited the restaurant and both drove over to Dawn's house. The two rushed inside happy to be out of the cold, and even made some hot chocolate to warm themselves up.

"You didn't see May at work did you?" Ash asked, since he didn't see much from his dishwashing station.

"No, she was off today, but she told she hates it there, not sure why though, I think its fine." Dawn told him.

"Hates it? That's odd. I think its fun, and I'm the one washing dishes all day haha!" Ash joked. The rest of the afternoon was spent with Ash trying out every piece of furniture in Dawn's house and deciding which ones was his favorite. Just as Ash was leaving Gary pulled into the driveway, who was going to the rest of the night with Dawn.

Ash drove back home, who, again being super tired went straight to bed. Ash had the next day off, so he was able to spend some time with Pikachu, and work on some homework. Ash was spending the day relaxing until his phone started vibrating. Ash looked to see a text from May.

After reading the text Ash got up and headed over to May's house, kind of sad that his relaxation session had been interrupted, but he was sure he would have fun at May's house. Turns out it wasn't May who wanted to hang out with him, but Max. May left for work shortly after Ash had arrived, and it was clear to see that she was not looking forward to going back to work. Ash and Max talked for hours about Pokémon and battling. It wasn't till nearly 8 p.m that Ash got a call from his mother wondering where he was. Ash figured he should probably go home and get some sleep.

The Next Day

It was an odd day at Kanto High; May was being unusually quite and almost seemed to be avoiding everyone. Even at lunchtime May was nowhere to be found. She was still at school, so Ash and Dawn were pretty confused as to what was going on. The two met up after school and both had the same idea in their head, they had to figure out why May was acting so strange. Unfortunately they'd have to put that off for another day, as right now they had to go work again.

Ash walked out of work several hours later only to be stopped by Dawn, who happened to be done at the same time.

"Ash!" She said as she pulled him aside.

"So I asked our boss if May was working today. Turns out she doesn't even work here anymore, she quit after the first day!" Dawn told him.

"So that's why we haven't seen her here lately haha. But that doesn't really explain how she was acting today does it?" Ash replied.

"Unless she was scared to tell us for some reason, which I don't think is something that she would do." Dawn suggested.

"But she didn't tell us that she quit, maybe that is like her. Let's ask her about it tomorrow." Ash said.

"Hmm, but the soccer game is tomorrow, why not ask her tonight?" Dawn suggested, deciding that if May was scared or mad at her that it would be better to get this over with tonight.

"Let's drive over to May house then, we can take my car." Ash offered. Dawn hopped into the car and they drove to Pewter City, curious as to what May was up too. They parked down the road and walked together towards the house. It wasn't until they neared the house that things got suspicious, as a car pulled into the driveway of the house.

"Wonder who that is?" Ash asked not paying much attention to it.

"Who knows, lets just get this over with." Dawn said.

A moment later May opened the door and walked out to meet the car, and got in the passenger seat. The car drove backwards off the driveway, and down the road. Ash and Dawn were only able to make out the silhouette of a boy who was driving the car.

"Any guesses who that could be?" Dawn asked.

"No idea. We'll looks like we just missed her, I guess we'll try again tomorrow." Ash said, before Dawn cut him off.

"Not so fast, quick get in the car, we're going to follow them!" Dawn said as she pulled Ash back to the car.

"Dawn, isn't that like really stalkerish? And why are you so concerned about where she's going?" Ash asked.

"I'm not sure. Something just seems fishy." Dawn told him as they started the car.

By now the car had been long gone, so they ended up driving around Pewter City blindly looking for it. After nearly a half hour of looking around they eventually gave up and headed back to Viridian City.

"There it is!" Dawn yelled, causing Ash to flinch and slam on the brakes.

"There's what?" And are you trying to get us killed?"

"The car, its right over there!" Dawn pointed out to Ash. They parked the car and walked over towards the other vehicle, which happened to be next to a restaurant. Neither of them could spot May through the window, so they went back to Ash's car and waited it out. About a half hour later May finally emerged from the restaurant.

"Oh my god!" Dawn said, realizing that May had finally come out.

"Is that Drew with her? There's no way!" Dawn said.

"Why would she be with Drew?" Ash asked questioningly.

"I don't know. But the only reason they'd be out eating together would be if they are on a… on a…. date."

"A date? But they just broke up awhile ago." Ash said.

"Think about it Ash, what else would they be doing here?"