Brock took a large swig of Jack Daniels as he laid upon his bed, his mind heavy with defeat. The homecoming dance had come and gone, and once again, Brock failed to take any girl home. Ash sat on the floor next to him, watching his friend grimace at the taste of the alcohol.

"Here," said Brock as he handed the bottle over to Ash. "This will numb the pain."

"Thanks," Ash replied, taking a small sip of the adult beverage, wincing as it burned his throat. He did not care for alcohol.

"Nurse Joy…" Brock whimpered as he grabbed the bottle back from Ash, taking another long swig.

"Take it easy," said Ash, trying to console his friend.

"You and me, man. Another year going home empty-handed…" lamented Brock as he clutched the bottle to his chest. The disappointment was palpable in his voice.

"Yeah, you and me, man," Ash replied with a strained smile. In truth, Lillie had invited him back to her house after the dance. But a sharp glare from her bodyguard, Paul, instantly ended that idea. The night of fantastical romance and dancing had ended, and Ash was now binge-drinking with his friend.

Brock choked down the remainder of the bottle. "Damn, out again. I should have bought more."

"You've had enough anyway," chided Ash. "Basketball season starts soon."

Brock stood up from his bed, wobbling ever so slightly. "About that," his usual spiked up hair seemed dead as it laid flat on his head. "We need five players to qualify for the regional tournament. We only have four."

"What?" Ash looked confused at Brock. "I thought we had those freshmen joining."

Brock swung the empty bottle through the air, as if it were a club. "I caught up with them at the dance. They said they're joining the tennis club instead," he explained.

"They seemed so excited to join during the pickup game," Ash replied, watching his friend continue to swing the bottle around. "What happened?"

"Well, rumor has it that a girl named Serena is joining the tennis team, and a bunch of guys are picking up tennis just to have a shot with her," Brock explained to Ash.

Ash's eyes lit up with curiosity. "Serena?"

"Yeah, she's pretty popular alright," Brock said, stifling a yawn. "Anyways, unless we find a new members in time, we'll be out of luck."

"Damn," cursed Ash, unsure if he was mad at Serena's popularity among guys or the freshmen who bailed on the team. "I guess I'll start asking around."

Brock fell back onto his bed, laying silent for a moment before speaking. "Maybe I should join the tennis team, too."

"Dude, you can't do that. We promised Damian we would make it to regionals this year." shouted Ash.

"Ah, what's the point? We can't go far." Brock rolled over, turning away from Ash. "Besides, maybe the freshman are right. Seeing Serena in a tennis uniform everyday doesn't seem so bad." Brock began to giggle as he trailed off into fantasy.

Ash sighed. "Get it together, Brock." Although he also couldn't help but imagine Serena in a tennis uniform. The image of her delicate blue eyes looking up at him, the same eyes from all those years ago. Their conversation from earlier in the night replayed over and over in his head.

"Oh yeah, that's right," Brock shot up from his bed. "I almost forgot, did you ever remember where she was from?"

"Sort of," started Ash. "I met her at a summer camp when I was a kid, but a lot of my memory is still hazy."

"Must be nice!" shouted Brock. "You have an easy conversation starter with her."

"I guess so," Ash said, remembering Marnie's words from earlier that night: "Serena was happy to talk with you."

A sudden buzzing sound emanated from Ash's pocket, interrupting his thoughts. He took out his phone, curious about the late-night notification.

Lillie: Hey I had so much fun tonight
Lillie: I was thinking, would you like to go to the movies with me tomorrow at noon?
Lillie: *heart emoji*

"Whats up?" Brock rolled over, peering into Ash's phone.

"It's Lillie, she… wants to go to the movies tomorrow." Ash's voice was tinged with uncertainty.

Brock sat up, his eyes widening in surprise. "Really? Man, I thought you blew it!" He looked at Ash, noting his muted expression. "… You are going to go, right?"

"Yea, of course." Ash replied. "But I'm not sure what to say."

Brock shook his head. "You over complicate things Ash. Just be yourself."

Nodding, Ash racked his brain for a moment. He didn't want to seem to desperate, but he also wanted to sound excited. What word choice would give the best impression?

"Here, let me do it." Brock reached over and snatched the phone from Ash.

"Dude!" Ash jumped up, reaching for his phone.

"Hold on man, I got this." said Brock, shoving Ash away. "Alright, and… done! Here, I rizzed her up for you."

Brock tossed Ash's phone back to him. "You asshole," mumbled Ash as he looked at his phone.

Ash: Sounds good.
Ash: *Thumbs up emoji*

"See, that wasn't so hard," Brock got up and dug around under his bed. After a moment he pulled out mason jar of 'Oddish'. "In celebration!" He said, cracking open the jar and letting the aroma flood the room.

"That's enough, Brock." Ash said, snatching the drugs from his friend.

"Ugh, I'm so hungover."

Serena felt nauseous as she walked alongside Marnie and Chloe, her two friends.

"This restaurant is so good, trust me!" said Chloe excitedly as she led the group of girls. "So Serena, are you excited for tennis club?"

Serena groaned inwardly at Chloe's questioning. She knew that Chloe was just trying to distract her from her hangover, but her headache was killing her "Yeah, I guess," she replied, trying to sound enthusiastic. "I just hope I can fit in."

Marnie laughed. "You'll be fine, although if you continue drinking as much as last night you might die before ever playing."

Serena rolled her eyes, but she couldn't help but crack a smile. "I've learned my lesson, trust me," she said, feeling her head throb with every step she took.

Chloe grinned mischievously. "I did warn you about those tequila shots, didn't I?" she teased.

Serena shook her head. "Yeah, yeah, I know. I should have listened to you."

Marnie as she stopped dead in her tracks. "Uh oh…" she muttered. A young couple was walking across the street from the girls. The boy was tall with messy black hair, and he was walking beside a girl who wore a large floppy sun hat. They were holding hands and walking up towards the movie theater.

"Ah, thats..." said Chloe quietly as she looked towards her friend.

Serena's heart sank as she watched Ash and Lillie walk into the movie theater. She had been trying to avoid thinking about him since last night, but seeing him with Lillie brought back feelings of jealousy. She knew that she shouldn't feel this way - after all, she had never even told Ash how she felt - but she couldn't help it.

Chloe and Marnie exchanged a worried glance. "Hey, don't worry about it," said Chloe, trying to cheer her up. "There are plenty of other guys out there. I can introduce you to some of Goh's friends."

Serena forced a smile, but she couldn't shake the feeling of disappointment. She had been holding onto hope that Lillie was nothing more than a one-time dance date, but it seemed like more than that.

"Come on, let's go eat." said Serena as she tried to push the thought of Ash out of her mind. She had other things to focus on, like tennis club and the upcoming tests.

But no matter how hard she tried, she couldn't get the image of the young couple out of her mind. For the remainder of the semester, the two remained on her mind.

Ash Ketchum couldn't help but admire how different Lillie looked in her tennis outfit. Her hair was up in a neat ponytail, and her usual regal attire was replaced with a sporty white miniskirt. "Wow, you look like a pro!" Ash exclaimed, grinning at her.

Lillie laughed, tossing a tennis ball into the air. "Thanks, Ash! I'm excited to play with you."

"Me too," Ash replied, his eyes fixed on the ball as Lillie served it towards him. He dashed forward, tracking the ball. His speed something he always had confidence in, but Lillie was no slouch. The ball had been sent hurdling towards the left baseline. Jumping, Ash extended his arm as far as possible, blocking the ball from landing and successfully returning the serve.

"Wow! Nice one, Ash!" Lillie cheered with a surprised smile on her face. "You're quite the athlete."

"Haha, I'm just barely keeping up," Ash smiled as he looked across at Lillie wiping sweat from her forehead. Her pulled back hair leaving her high cheekbones on full display.

It had been three weeks since the school dance, and Ash couldn't believe how much time he had been spending with Lillie. They had gone to the movies, the zoo, and they had even taken a short day trip to Celadon City. Her once intimidating rich demeanor had faded away, as she opened up more and more to Ash. He began to notice all the little things about Lillie, like how she would instinctively cover her mouth in shock, or her insistence on helping Ash study for his mathematics test.

"Alright, here I go," Ash said, casually tossing the ball up into the air. Treating his arm like a whip, he cracked down on the ball and sent it towards Lillie's court. He felt a surge of adrenaline as he watched the ball fly towards her. Ash had placed the ball across from Lillie, awaiting her move.

"Hah!" The blonde-haired girl narrowly returned Ash's serve. However, it was a trap, she had placed the ball exactly where he wanted it.

"Hi-yah!" Ash shouted as he cut through the air with his racket. The ball shot back towards Lillie, going straight between her legs. Crashing into the pavement, the ball bounced once before hitting the wall behind Lillie.

"Wow..." Lillie said dumbfounded as she looked at Ash. "Are you sure you've never played tennis before?"

"Just lucky, I guess," Ash said meekly.

"Well well well, if it isn't Ash Ketchum."

Out of nowhere, a voice that was both shrill and deep pierced the air. A tall lanky teenager with spikey brown hair came out into the sunlight. Large black shades covered his eyes. Sporting a bright off-white shirt and neon pants, he certainly stood out.

"Gary?" Ash asked confused.

Lillie looked at Ash. "A friend?"

"Best friends." Gary said, not giving Ash time to reply. "Check this out dude, turns out my Gramps is kind of loaded."

Gary started to pose, showing off his 'fit' to Ash and Lillie. "This brand is called PRADA. Do you even know what that is, Ash? I got a few pairs if you wanna borrow some-"

"I'm fine." Ash cut him off. "Lillie and I are actually headed out."

"Wait a second Ashy boy," said Gary. "I saw you on the court just now, nice moves."

"Thanks, I guess," replied Ash.

Shooing Lillie away, Gary Oak walked to the court across from Ash. The light reflecting off his shades nearly blinded Ash.

"Let's play a set." Gary's tone oozed arrogance. "I can't let you leave without humbling you first."

Ash stared at Gary, his smug smile seemingly kept growing. He wanted nothing more than to wipe that grin off of his face. On the other hand, there was a chance Ash would embarrass himself in front of Lillie.

"Ash you can totally win!" Lillie said as she rushed over to him. She seemed to be bouncing up and down in excitement.

"You can't let your girl down, Ash!" Gary smirked as he retrieved his expensive tennis racket from it's case. After jumping in the air a few times, he stared down at Ash. "Come on, let's do this."

A wicked idea came to Ash's mind. "Actually Gary, let's make this more exciting." He grinned slyly as he spoke. "Let's place a wager on this."

Gary looked confused. "A wager?"

"Yea, if I win, you have to join the basketball team."

"The basketball team?"

"Yup," replied Ash. "You're tall enough for it, not to mention athletic."

Gary seemed confused for a moment, before finding his patented smirk. "Alright, Ashy-boy. I'll take you up on that offer, but if I win, I want something big."

"What? I only have twenty dollars on me." said Ash.

"Oh no, I don't want money Ash. If I win, I get to take Lillie on a date." Gary grinned as he watched the rich girl's excited face turn to confusion.

"Why the hell would I agree to that?" Ash glared at Gary, annoyed.

"Don't be scared Ash, protect your maiden." chuckled Gary.

"It's okay Ash," Lillie walked over to Ash, grabbing his hand. "I believe in you!"

"Are you serious?" Ash looked confused at his girlfriend. She gave him a small nod and squeezed his hand tightly.

"Don't worry, even if you lose Paul will prevent Gary from dating me." she said in a hushed tone. "Also, you need new members on the basketball team, right?"

Ash watched Lillie's eyes sparkle with excitement. "Alright Gary, I'll do it." he said.

"Seriously?" Gary looked surprised over at Lillie as she fixed her ponytail. "No way, awesome!"

Ash narrowed his eyes at his opponent. Gary had an inch or two on Ash, and it was clear from the muscle definition through his designer shirt that he had power behind his swing. From an outsiders perspective, it seemed Gary had the clear advantage.

"Man, you're gonna regret this." With a smirk, Gary casually tossed the ball up into the air, bringing his racket down onto it.

Gary got off to a hot start, using his superior strength and rhythm to take the early lead. Staying calm, Ash began to dissect Gary's play. While Gary was stronger and more skilled than Ash, Ash had a clear speed advantage. Gary was also too head-strong, refusing to attempt any different serves even after Ash started to adapt. Using his superior speed, Ash worked his way back from the deficit.

"Match point," said Lillie as she watched Gary threw the ball up and brought his racket down with a slam.

"Now!" Ash thought as he dashed along the baseline of the tennis court, reading the trajectory of Gary's serve before it even left his racket. Gary was too straight forward to implement any kind of trick or deception, he wanted to beat Ash with strength alone.

Even knowing where the serve was going, Ash still barely reached it. Diving, he swiped the racket at the ball, just barely grazing it. Flying slowly through the air, the ball grazed the top net. Through what can only be described as pure luck, the ball came with enough force to fall onto Gary's side.

6-4. Ash had won.

"Wow, Ash!" Lillie ran over and grabbed both of Ash's hands, helping him up. "That was amazing!" The girl's arms wrapped around Ash as she hugged him, bouncing up and down with excitement.

"Uh, Lillie." Ash blushed as he turned his face slightly, feeling the girl's body press against his

"Ah, sorry." Lillie's face turned bright red as she retreated her arms back towards her side.

Gary frowned as he removed his expensive glasses. "Well, you win. Here you go."

"I don't want those, Gary."

"Huh?" Gary gave a dumbfounded look. "Oh that's right, the basketball team."

"Yea," replied Ash. "Tryouts are next week."

Gary frowned for a moment, before finding his patented smirk. "Alright, Ashy-boy. A deal's a deal. I'll tryout for the basketball team." Walking up to Ash, he extended his hand. "You're pretty fast, next time, I won't hold back."

Ash looked at Gary's hand. The same hand that shoved Ash when they were children. Smiling, Ash shook it. "It was a good match."

"Is that really alright?" Lillie asked. "He doesn't look like the type to practice."

Ash and Lillie walked hand-in-hand down a sunset painted road. The two decided to walk back to Lillie's house, rather than take her limousine.

"I don't really have a choice, nobody else I asked wants to play," replied Ash. "Which reminds me…"

Ash turned around and looked down the road. About twenty paces away walked Paul. The massive bodyguard had been keeping watch of the couple the entire day. He was always watching, silently.

"Ash?" Lillie looked over as he observed the bodyguard.

"Could you ask Paul to join the basketball team for me?" Ash continued to look at the massive teenager. Despite being presumably the same age, he dwarfed Ash. His height would surely be useful on the basketball court.

Lillie brought her small finger to her lip. "Hmm, I'll have to ask my mother for permission, but if I ask him to play I think he will."

"Really?" asked Ash excitedly.

"Of course. He plays with my brother regularly." said Lillie with a smile.

The pair continued to walk along the sunset road back towards town. As they walked, Ash couldn't help but admire the way Lillie's hair danced in the gentle breeze. He watched as the girl took in the temperate late summer scenery around her.

"Hey Ash." Lillie's turned to Ash. "Can I ask you something?"

"Sure, whats up?"

"Do you know what you're going to do after high school?" asked Lillie.

After high school? Ash rarely even thought about tomorrow. He paused for a moment, taken aback by Lillie's question.

"I'm not sure," said Ash, feeling inadequate in his response. "What about you?"

"My mom has a path planned out for me," said Lillie dejectedly. "But I'm not sure if it's the right one."

Ash had never met Lillie's mother in person, but he had heard all about her. She was one of the richest women in the entire country. Not to mention the CEO of the Aether Foundation, which Ash's family relied on for housing assistance.

"University?" asked Ash, looking into Lillie's face.

"Something like that…" Lillie stared back off into the sunset.

The couple continued down the road in silence. After a few minutes, they arrived at the gate to Lillie's massive mansion. Large walls surrounded the estate at every angle.

"Well, I'll see you tomorrow at school." Ash watched as a pair of bodyguards unlocked the tall gate and let Lillie inside.

"Goodnight Ash," Lillie looked at him through the gate. "See you tomorrow."

Ash watched as Lillie entered her house. A strange feeling came over him as he saw her disappear inside.

"Days over, time to go home." A deep voice drew Ash's attention, it was Paul's. The massive man positioned himself in front the gate. "Don't linger too long, or I'll have to call the cops."

Ash gave an awkward nod and hurried home, trying to shake off the feeling of being watched as he walked home in the night. Turning, he gave the mansion one last look. The walls seemed even taller in the new moonlight, ensuring nobody could get in, or out.

Serena slouched into her chair. Professor Birch stood at the front of the class droning on about the term project, and the young girl had long stopped listening. Instead she had propped up her phone in front of her open textbook, mindlessly tapping away.

Chloe: Oh my god, the boys take gym class sooo seriously
Serena: Ugh, I know.
Serena: This class is boring af *sleeping emoji*

"Serena!" The Professor's voice snapped Serena back to reality.

"Yes!?" she squeaked.

"Please find a group to pair up with… and please do not use your phone in my class."

Serena's face turned red with embarrassment. Looking around, she saw various students congregating into groups of four. She watched as the various groups of friends paired up. For a second, she worried if she was too late.

"Let's go, Serena." Marnie walked up with her usual bored expression. "Come join the group."

"The group?" thought Serena as she followed her friend.

"We're ready." Marnie's voice droned as she looked at the two remaining team members. "Let's get this over with."

Serena looked over to see a sleeping Ash. His face was buried in his arms, with only his messy dark hair sticking out. A common sight. Next to him was Gary Oak, who was leaning back in his chair, picking his ear.

"This is gonna blow," said Gary as he flicked his fingers.

"Shut up," Marnie said bluntly. "You're going to work hard on this project."

"Or what? You'll cast a spell on me?" Gary smirked at the girl. "Oooooo, I'm so scared. Don't hurt me, emo!"

Marnie rolled her eyes and looked over at Serena. "I did this for you," she seemed to say.

Ash Ketchum took a large yawn and buried his face back into his arms. "Sounds good." he muttered, still in dream land.

"Whats our project on anyway? I wasn't paying attention." asked Gary.

Marnie glared at Gary. "Ionic bonds, and if you mess up my grade I'm going to attack you."

"Oh no, the attack of the emo! How will I ever survive." Gary said, chuckling at his own joke.

Marnie and Serena pushed their desks together with Ash and Gary's, forming a large

table. Gary continued to bicker with Marnie, and Ash continued to sleep. Serena tried her hardest not to look at the sleeping boy, but she constantly found herself watching him.

Marnie pointed to a graphic in the textbook. "You idiot, that's a covalent bond. Ionic is when the atom donates an electron."

"Damn you're an emo and a nerd!" cried Gary as he leaned so far back in his chair it appeared he would fall.

"And you're ugly and stupid," scoffed Marnie.

Gary pouted as he slumped on his desk, looking at his blonde partner. "Serena help, Marnie's bullying me!"

"Hey now, you two," Serena said softly, unsure at how to mediate.

"Help me out, bro!" said Gary as he kicked Ash's desk.

"Huh? What?" Ash popped his face up confused. His tired eyes looked around his group. His eye's hit Serena's, which seemed to jolt the boy awake. "What's up? Sorry, long night last night."

"This emo is bugging me, bro." said Gary as he threw an arm around Ash's shoulder. "Explain to this emo that I'm the next Micheal Jordan. I don't need school."

"You can barely hit a jumper," replied Ash, pushing Gary's arm off him.

"For now!" shouted Gary. "I'll be smoking you in no time."

"Hush you two, we need to focus," said Marnie as she opened up her phone. "Here, add my phone number. We'll have to work on this project over the weekend since you too are so unfocused."

"The weekend? Hell no!" protested Gary. "I got like three dates this weekend."

"Well you better cancel them all." replied Marnie.

Gary eyed Serena for a moment. "Alright, fine. But only because Serena is coming."

The group of four all exchanged numbers. As Serena inputted Ash's number into her phone, Marnie gave her a slight nudge. Her plan had succeeded.

"Don't text me too much or I'll block you." Marnie said to Gary.

"As if I'd text you." Gary scoffed as he turned towards Serena and gave her a smile. "Especially when I have this cutie in my phone."

"Ahaha, thanks." Serena forced a smile in return.

"Alright, I'll see you all on Saturday." Marnie stood up and started pushing her desk back. "Come on Serena, I'll go insane if I have to spend anymore time with that idiot."

Ash watched the two girls move back to the front of the room.

"Yo, dude." Gary gave his patented punch to the shoulder to get Ash's attention. "Did you see the way Serena was looking at me, bro? She's one hundred percent into me, I can tell."

Ash sighed loudly "Come on Gary, not this again," he said, as Gary's wishful thinking continued until the class bell.

End of Chapter 2

Character Profiles

Ash Ketchum
Age: 16
Dating: Lillie Celeste
Best class: Earth Sciences.
Worst class: Mathematics
Likes: Basketball, Video Games, Lillie
Dislikes: Math class, Gary Oak
"He needs to stop sleeping in my class!" - Professor Birch

Serena Summers
Age: 15
Dating: n/a
Best class: Literature
Worst class: Earth Sciences
Likes: School, Fashion, Ash
Dislikes: Earth Sciences
"She's so fire bro!" - Gary

Lillie Celeste
Age: 16
Dating: n/a
Best class: All of them.
Worst class: n/a
Likes: Playing golf, reciting ballet, Ash
Dislikes: Sweets
"I once heard she got a girl expelled just for looking at her!" - Misty

Gary Oak
Age: 16
Dating: ?
Best class: n/a
Worst class: All of them.
Likes: Women, picking up women, partying.
Dislikes: Alarm clocks, tests
"This guy sucks." - Marnie

Brock Ishiou

Age: 18
Dating: n/a
Best class: Culinary studies
Worst class: Mathematics
Likes: Nurse Joy, women, basketball, alcohol
Dislikes: n/a
"He needs to stop smoking." - Ash

Paul Berimont
Age: ?
Dating: n/a
Best class: ?
Worst class: ?
Likes: n/a
Dislikes: Ash Ketchum, people who harm Lillie.
"He's been my bodyguard ever since we were children." - Lillie

Marnie
Age: 16
Dating: n/a
Best class: Language Arts
Worst class: Gym
Likes: Nothing
Dislikes: Gary Oak
"I caught her playing with a spider!" - Chloe