Pursuing Cynthia

Chapter 1: Rebirth, Regrets, and Ridiculousness

When I woke up, the first thing I saw was a Bidoof staring me dead in the eyes.

And it was not just a normal stare—it was the kind of stare that screamed, "Your life is going to be as chaotic as mine."

"Oh great, I'm dead," I muttered, mostly because I couldn't remember how I got here. The last thing I recalled was chugging an energy drink, racing to my computer to catch a shiny Gible, and… well, I guess the *racing* part didn't end well. Who knew slippery floors and blind enthusiasm could kill a guy?

But now? Now I was lying in a meadow with a very curious Bidoof sniffing my face like I was the reincarnated essence of its long-lost Bidoofian ancestor.

"What are you looking at, buddy?" I groaned, shooing it away, but it just tilted its head and waddled closer.

That's when I heard it.

"You're awake!"

Not a human voice. Not a normal human voice, anyway. The voice belonged to a Pokémon—a Chatot perched on a branch, squawking like it was auditioning for *Pokémon Shakespeare in the Park.*

"You can talk?" I blinked.

"No, YOU can understand me!" Chatot corrected, puffing its chest proudly. "It's a rare skill. You must be very special!"

Great. I was special. Special enough to understand Pokémon in a world where everything—plants, weather, and quite possibly taxes—was powered by creatures that could breathe fire or shoot hyper beams.

After about an hour of wandering aimlessly through tall grass and avoiding random Starly attacks, I got the gist: I was in Sinnoh, the Pokémon world. And not just any Sinnoh—the Cynthia-is-still-single-and-beautiful era Sinnoh.

This is where things got interesting.

You see, even in my previous life, I had a favorite: Cynthia, the Champion of Sinnoh. She was smart, strong, elegant—everything I wasn't but desperately wanted to be around. My dream back then was simple: defeat her in battle, and then… uh… somehow charm her into coffee? I never planned that part out.

Now? Now the dream was real, and I had the ultimate chance to pursue it.

"Alright," I said, hands on my hips, staring down at the Bidoof that had followed me all the way from the meadow. "If I'm going to impress Cynthia, I need a team. You're going to be my first Pokémon!"

Bidoof tilted its head like I'd told it to perform calculus.

"C'mon, work with me here," I pleaded. "You're cute, you're sturdy, and you've got… uh… enthusiasm! That's all I need."

Bidoof let out a noise that sounded like a mix of a yawn and a laugh. I chose to interpret it as agreement.

"Congratulations, you've caught Bidoof!" Chatot chimed sarcastically.

"Caught? It's following me willingly!"

"Sure, sure," Chatot said, clearly unimpressed. "You're definitely Champion material already."

I made my way to the nearest town, Jubilife City, with the intention of getting properly equipped. I had no Poké Balls, no money, and no idea how to *not* embarrass myself in front of professional Trainers.

But then I saw her.

Cynthia.

She was sitting at a café, sipping tea and looking like a goddess descended from Mt. Coronet. My heart did what any self-respecting man's heart would do in this situation: it flipped, flopped, and attempted to perform *Volt Tackle* straight into my ribs.

"Alright," I whispered to myself. "Play it cool. No weird noises. No tripping over imaginary stones. Just go up and say hi."

I took a deep breath, patted my Bidoof for moral support, and began walking.

"Excuse me," I said, stepping up to her table.

She looked up, her golden eyes sparkling with a mixture of curiosity and mild suspicion.

"Yes?"

"I, uh…" My brain short-circuited. "Nice weather we're having?"

Cynthia blinked.

Chatot facepalmed—or would have, if it had hands.

"I mean, I'm new in town," I quickly added, hoping to recover. "Just arrived in Sinnoh. Big fan of, uh, battling."

Her expression softened. "A new Trainer? That's wonderful. Sinnoh is a great region to start your journey."

"Oh, I'm not just any Trainer," I said, puffing out my chest. "I'm going to be the next Champion."

Bidoof, who had been chewing on the leg of a café chair, chose that moment to burp loudly.

Cynthia raised an eyebrow.

To make matters worse, a random Zubat flew into the café, causing a chain reaction of chaos. Plates shattered, people screamed, and Cynthia's tea spilled everywhere.

"Don't worry!" I shouted, leaping into action. "I've got this!"

What followed was a display of heroics so bad it deserved its own documentary. I chased the Zubat with a breadstick, Bidoof tackled the wrong chair, and Chatot provided unhelpful commentary the entire time.

"Careful! You're about to—"

*CRASH.*

"—trip over that table," Chatot finished as I landed face-first into Cynthia's now-ruined dessert.

When the dust settled, Cynthia was standing over me, a mixture of amusement and pity on her face.

"Well," she said, offering me a hand, "you've got enthusiasm. That's a start."

As Cynthia walked away, leaving me to pay for the damages (thanks, Bidoof), I couldn't help but grin.

Sure, I'd made a fool of myself. Sure, I'd faceplanted into cake. But Cynthia had *noticed* me, and in my book, that was a win.

"Alright, team," I said, turning to Bidoof and Chatot. "We've got work to do. Step one: catch stronger Pokémon. Step two: become a Trainer worthy of Cynthia's attention. Step three: figure out how to talk to her without mentioning the weather."

"Step four," Chatot chimed in, "don't embarrass yourself next time."

"Exactly!" I nodded. "This is just the beginning!"

Bidoof burped again.

After Cynthia left the café, I spent the next ten minutes arguing with the café manager over the damage bill. Apparently, they don't accept promises of future Champion glory as currency. By the time I staggered out of Jubilife City with Bidoof and Chatot in tow, my confidence was bruised, my wallet was still empty, and I was pretty sure the Zubat incident had earned me a permanent ban from at least three businesses.

But none of that mattered. Cynthia had *noticed me*!

Sure, she probably noticed me the same way you notice a Snorlax blocking the road, but hey, progress is progress.

"Alright, team!" I declared, standing in the middle of Route 203. "The first step to impressing Cynthia is building a strong team. And the first step to building a strong team is catching another Pokémon!"

"What about me?" Chatot asked.

"You're already on the team," I said. "You're the snarky commentator who keeps me grounded."

Chatot flapped indignantly. "I'm also capable of battle, you know!"

"Sure, sure," I said, waving it off. "But let's be honest: we all know Bidoof is the real MVP here."

Bidoof, bless its little derpy soul, was currently gnawing on a rock with the determination of a Machamp lifting a mountain.

Chatot sighed. "We're doomed."

As we wandered through the tall grass, I finally spotted my target: a Shinx, its fur crackling with electricity.

"Perfect!" I whispered. "That'll look *so* impressive on my team!"

Chatot rolled its eyes. "You don't even have Poké Balls."

"Details, details," I muttered, crouching low. "Here's the plan: Bidoof distracts it with sheer cuteness, and I… uh… improvise!"

"Bidoof doesn't know 'cuteness,'" Chatot pointed out.

I ignored it and turned to Bidoof. "Alright, buddy, use—uh—Tackle!"

Bidoof looked up from its rock, gave me a blank stare, and then waddled toward the Shinx with all the speed of a slowpoke on vacation.

Shinx blinked, clearly unimpressed.

"Okay," I whispered, "Plan B: Charge in myself!"

What followed was what historians might one day call "The Great Shinx Disaster."

As I lunged at the Shinx, hoping to somehow wrangle it with my bare hands, it zapped me with a spark so strong I saw my past, present, and potential future flash before my eyes.

"AAAAAAAAA!" I screamed, flailing backward into a bush.

Chatot cackled. "Ten points for enthusiasm! Zero for execution."

"Fine!" I wheezed, smoke curling from my hair. "Plan C: Team effort!"

With some coaxing (read: begging), I convinced Chatot to help. While Chatot swooped in to distract the Shinx, Bidoof finally remembered it could tackle things and launched itself at the poor electric cat.

The result? A pile of flailing fur, feathers, and teeth that somehow ended with the Shinx tangled in my jacket.

"Great!" I said, holding up the squirming Shinx like it was Simba from *The Lion King.* "Now, let's—wait, how do I *keep* it?"

Chatot sighed. "You can't just hold onto it like it's a plush toy!"

"Why not? It's working so far."

Shinx let out a growl, and I got the distinct feeling that if I didn't let go soon, my face would become its new scratching post.

Reluctantly, I set it down, and the Shinx immediately bolted into the grass, leaving me with nothing but a sore ego and a slightly dazed Bidoof.

"Well, that could've gone better," I admitted.

"No kidding," Chatot said, fluttering to my shoulder. "You're really starting to convince me that Cynthia doesn't stand a chance… against secondhand embarrassment."

As we trudged toward Oreburgh City, my spirits were low. I had no new Pokémon, no money, and no idea how to become Champion material.

That's when I heard a familiar voice.

"Excuse me, are you alright?"

I turned to see none other than *Cynthia*, standing on the path like an angel sent to mock my very existence.

"C-Cynthia!" I stammered, my brain going into overdrive. *Play it cool, man. Play it cool.*

"I thought I heard some commotion," she said, her eyes flicking to Bidoof, who was now chewing on my shoelaces. "Are you… training?"

"Oh, you know," I said, trying to sound casual. "Just… strategizing. Big plans. Very big."

Chatot muttered under its breath, "More like big disasters."

Cynthia smiled, and I swear the entire route got ten times brighter. "That's good to hear. Every Champion starts somewhere."

"Exactly!" I said, puffing up my chest. "And I'm starting… here. On Route 203. With, uh…" I looked at Bidoof. "...potential."

Her gaze softened, and I wondered if maybe—just maybe—she thought I was charming instead of completely hopeless.

"Well," she said, "if you ever need advice, don't hesitate to ask."

As she walked away, I stood frozen, basking in the afterglow of her presence.

"Wow," I whispered. "She talked to me again. Twice in one day!"

Chatot sighed. "At this rate, she'll propose to you by the time you accidentally stumble into the Elite Four."

With renewed determination, I turned to my team.

"Alright, listen up!" I said, hands on my hips. "We need a new plan. No more winging it!"

"Define 'plan,'" Chatot quipped.

"A strategy. A roadmap. Something that doesn't involve me getting electrocuted or ruining Cynthia's tea."

Bidoof burped again, and I took it as agreement.

"Step one," I said, raising a finger, "catch a new Pokémon—properly this time. Step two: earn some money. Step three: train until we're strong enough to take down a Gym."

"And step four?" Chatot asked.

"Step four: figure out how to actually battle without embarrassing myself."

Chatot nodded. "Ambitious. Stupid, but ambitious."

"Exactly!" I said, grinning. "Now, let's get to work!"

The plan was simple. No more winging it, no more embarrassing moments (hopefully), and definitely no more tackling wild Pokémon without Poké Balls. I'd find a way to make money, catch a real team, and work my way toward Gym battles. From there, it'd be an easy ride to becoming Sinnoh's Champion and winning Cynthia's admiration.

It was foolproof.

Unfortunately, I was the fool implementing it.

As we made our way toward Oreburgh City, the reality of my situation began to sink in. I had no money, no Poké Balls, and no way of earning either. Chatot wasn't shy about reminding me.

"Explain again how you plan to train without supplies?" it asked, lazily perched on my shoulder.

"I'll figure it out," I grumbled. "Trainers have to start somewhere, right?"

"And most of them start with *money.*"

Ignoring Chatot's sass, I scanned the path for anything that could help. Maybe a kind stranger would give me something. Maybe there'd be a loose Poké Ball lying around. Maybe—

"Yo, kid!"

I turned to see a young Trainer, probably no older than twelve, standing a few feet away. He had a confident grin, a baseball cap tilted backward, and a Poké Ball in hand.

"Wanna battle?" he asked, bouncing on his heels. "Winner gets 500 Pokédollars!"

I froze.

This was it. My chance to earn money and prove my worth as a Trainer. Sure, I only had Bidoof and Chatot, but how tough could this kid be?

"You're on!" I said, pointing dramatically.

The Trainer grinned and sent out his Pokémon: a Machop that looked like it spent its free time bench-pressing Graveler for fun.

My confidence wavered.

"Uh, okay," I muttered, turning to Bidoof. "You've got this, buddy."

Bidoof waddled onto the battlefield, its expression a mix of determination and mild confusion.

"Machop, use Low Kick!"

Before I could even process the command, Machop launched itself forward and swept Bidoof's legs out from under it. My trusty starter let out a startled squeak before landing on its back, utterly defeated.

"That was fast," Chatot remarked.

"Not helpful," I hissed. "Alright, your turn!"

Chatot flapped into the air, glaring at me. "I'm not a battle bird, you know."

"You're my last hope! Do something!"

Chatot sighed, then turned to the Machop. "Alright, you over-muscled noodle, let's see how you handle this!"

To my surprise, Chatot actually managed to land a couple of Peck attacks before the Machop swatted it out of the air like an annoyed parent dealing with a persistent mosquito.

"Chatot is unable to battle," the kid announced, smirking. "That's my win!"

I fell to my knees, my pride and wallet both empty.

The kid handed me a potion out of pity before heading off, leaving me to sulk on the side of the road.

"Great," I muttered. "I lost my first real battle. Cynthia's definitely going to fall for a loser like me."

"Oh, stop moping," Chatot said, limping back to my shoulder. "At least now you know what not to do."

"Yeah," I said, glancing at Bidoof, who was still lying on its back like a beached Wailmer. "Step one: find a tougher Pokémon."

"Step two," Chatot added, "maybe don't challenge anyone with biceps bigger than your entire body."

"Noted," I said, hauling Bidoof onto my lap. "But seriously, how am I supposed to catch anything without Poké Balls?"

Chatot tilted its head. "There's always the Poké Mart in Oreburgh City."

"With what money?"

Chatot was silent for a moment, then said, "Ever considered panhandling?"

Desperation breeds creativity—or, in my case, stupidity. With no better options, I decided to put on a *performance* in Oreburgh City's main square.

"Step right up!" I called, standing on a makeshift stage (which was really just a crate I found). "Marvel at the incredible talents of Bidoof the Great and Chatot the Magnificent!"

Bidoof, clearly unaware of its new title, was busy chewing on the edge of the crate. Chatot, on the other hand, was quick to voice its complaints.

"Are we seriously doing this?" it squawked.

"You got a better idea?" I whispered through gritted teeth.

Chatot sighed but went along with it. "Ladies and gentlemen!" it called, flapping its wings theatrically. "Prepare to be amazed!"

What followed was a "performance" so bad it probably lowered the city's overall reputation. Bidoof attempted a backflip and fell on its face. Chatot recited random Shakespeare lines for no discernible reason. And I… well, I mostly tried not to die of embarrassment.

By the time we finished, we'd earned a grand total of 100 Pokédollars, a bruised ego, and one tomato to the face.

Just as I was about to give up, a stranger approached. He was an older man with a kind smile and a bag of supplies slung over his shoulder.

"That was… unique," he said, handing me a Poké Ball.

"Seriously?" I asked, staring at the ball like it was a miracle.

He chuckled. "Every Trainer needs a chance to start somewhere. Just promise me you'll use it wisely."

"You've got it!" I said, practically bouncing with excitement. "Thanks, uh… what's your name?"

"Just call me Rowan," he said with a wink before disappearing into the crowd.

Armed with my first Poké Ball, I was ready to try again. This time, I wouldn't make the same mistakes. I'd find a Pokémon, catch it properly, and—most importantly—keep my dignity intact.

"Alright, team," I said, marching toward the nearest patch of grass. "Let's make this one count!"

Bidoof burped. Chatot sighed. And somehow, I felt like this was only the beginning of an even crazier adventure.