Caitlin, who came from an average family background, wasn't able to fulfill her dream of studying at the Rustboro Trainer School three years ago.
Naturally, kind-hearted Cynthia couldn't bear to leave her friend, who wasn't quite ready to take care of herself alone in Sinnoh.
Also the thought of leaving her grandmother behind also weighed heavily on Cynthia's heart—just imagining it made her pale. In the end, she made the decision to join Caitlin and enroll together at the Jubilife Trainer School instead.
Of course, their friendship didn't end there. With the Pokétch enabling long-distance communication, it became easy for Allen, Cynthia, and Caitlin to stay in touch and even "visit" each other virtually. Most weekends, they would hold small catch-up meetings to chat and laugh like old times.
According to their promise, this year Allen would be joining both Cynthia and Caitlin to check out the newly opened PokeSkating Park in Jubilife City.
Roller skates, skateboards, and all kinds of park-based activities had suddenly exploded in popularity across Kanto, Johto, and Sinnoh. From little kids to college students, many now spent their weekends gliding through skateparks and practicing tricks.
The reason?
It all started with a viral sensation in Johto—an influencer who often filmed his Snubbull skateboarding in local parking lots.
The little Pokémon quickly captured the hearts of the community with its surprising skills and infectious energy. Nicknamed "The Bullgod," Snubbull even set a world record for the fastest 100 meters on a skateboard by a Pokémon.
Its fame skyrocketed after several appearances on popular shows like Greatest Johtonian Snubbul, and it soon became a fan favorite across the region. From there, the trend took off like wildfire—suddenly, everyone wanted to be like The Bullgod.
After arriving in Jubilife, Allen called his grandmother first to let her know he'd made it safely.
"It's good to see you've arrived safely," Grandma Dracelia said, letting out a small sigh of relief as Allen appeared on the video transmitter.
"Grandma, when I was in Rustboro, I often went to Littleroot by myself," Allen replied, giving his grandmother an unapproving look.
His grandmother's eyes narrowed. "What do you know, kid? Just because you could walk to the station on your own doesn't mean you're all grown up. There's been—"
And then the scolding began.
"Good. Now, eat properly, stay out of trouble, and don't forget to call your grandma every three days. Got it?"
"Yes, ma'am."
"Hmph, good that you know."
After talking for a while, the call ended, and Allen finally sighed in relief.
Jubilife City is the largest city in the Sinnoh region, known for its bustling atmosphere and modern landmarks.
Among its prominent locations are the Global Trade Station, the Trainers' School, the Pokétch Company, and the Jubilife TV Station. There's also the famous Jubilife Condominiums, a residential building seamlessly connected to the Global Wonder Station, contributing to the city's vibrant urban landscape.
But now the focus will be on the new Pokeskating trend!
The new skatepark in Jubilife City, with its well-maintained ramps and rails, provides an ideal space for Pokémon to showcase their skating skills. It's a sight to behold—Pokémon gliding with ease, their movements smooth and natural as they navigate the park.
Allen couldn't help but smile, though there was a slight twitch at the corner of his mouth.
In his previous world, pets were typically relegated to the sidelines while their owners played, but here... it was the opposite.
Pokémon were skating, rollerblading, and having fun, while their trainers sat on the sidelines, chatting away or engrossed in their phones. Wasn't this supposed to be the other way around?
"Hey, Wait for me!" A Shinx zipped effortlessly across the half-pipe, its electric mane sparking as it glided through the air, leaving its trainer scrambling to catch up in a panic.
Nearby, a mischievous Bidoof rolled down a ramp on a skateboard, its wide grin as wide as the board beneath it. Meanwhile, a Munchlax sat perched on a bench, clutching a skateboard with a thoughtful expression—clearly debating whether the poor thing could handle the chonk or not.
Allen had been strolling around the square, enjoying the hustle and bustle, when suddenly, someone tapped him on the shoulder from behind.
He spun around, only to find—no one there. Turning back to the other side, the tap came again, this time from his right. He whipped his head around, only to be greeted with Caitlin's mischievous grin.
Perhaps because Cynthia was so famous in the anime, Allen hadn't noticed much change in her over the past few years. The little angel had simply grown into a slightly bigger little angel—just a little bit more serious.
But Caitlin's transformation? That was nothing short of earth-shattering.
She had ditched her old, unhygienic habits and started paying attention to her appearance. Her clothes were clean and neat, and her once watermelon-colored hair had grown so long and thick, it could rival Rapunzel's.
The biggest change, though, was her confidence. She used to hide behind Cynthia like a shy little bean, but now, she stood just as tall as Cynthia, and her demeanor had completely shifted.
"Why do you look so surprised? Is there something on me?" Caitlin asked, looking down at her outfit before nudging Allen.
"Yup, right here," he pointed at her nose. "You've got... snot."
Caitlin blinked for a second before her face flushed red. "Bastard!"
Before Allen could react, Caitlin kicked him lightly in the shin. "If you bring up my past, I'll expose those stories about you and your grandma's... disciplinary techniques."
"Who are you going to tell? You don't exactly have a friend—oops, sorry, I mean a gossip squad at school like Cynthia's."
"Allen, you're such a dog!"
With Caitlin hot on his heels, not missing a single opportunity to land a smack, Allen, naturally, did what any sane person would do—he ran like his life depended on it.
Suddenly, a shadow appeared above a kid, and when he looked up, he was shocked. He pointed and shouted, "What Pokémon is that?!"
Everyone around them quickly looked up, their jaws dropping in awe. Even Allen and Caitlin, who had stopped their playful chase, turned their heads toward the sky.
"Ga~!"
The dragon Pokémon soared gracefully through the air, its sleek, sharp body maneuvering with ease before it landed elegantly in the center of the square. A hushed silence fell over the crowd, all eyes fixed on the stunning Pokémon.
Gabite's piercing blue eyes scanned the area, its tail flicking side to side as it looked around. It let out a soft growl, almost as if it were sizing up the crowd, before finally spotting Allen and Caitlin.
"Ga~!"
"Oh, Cynthia! Gabite!" Allen waved his hand happily and ran toward them followed by Caitlin.
"You two, you always have to make a fuss whenever you meet. Stop it," Cynthia said, her voice a little annoyed, like a concerned older sister.
Caitlin, as always, listened to Cynthia. The moment Cynthia spoke up, she stopped and, almost reluctantly, explained herself. "Why do I need so many friends? I don't need that many. It's just too tiring to communicate with so many people. A few friends are enough…"
Outside of her interactions with Cynthia and Gothita, Caitlin was often seen alone at school. She occasionally spoke to other girls, but her conversations were always brief and detached, carrying an air of aloofness that set her apart from the others.
It seemed that only when she was with Cynthia, or occasionally Allen, did she allow herself to show her true side—relaxed, open, and unguarded.
Cynthia was relieved with her choice to choose Caitlin over Allen. She didn't know what would have happened if she had left her alone here in Sinnoh. It might have been too much for her to handle. But here, with her, someone who understood her, Caitlin had a chance to blossom, which made her happy.
"Allen looked back and forth toward them and couldn't help but give her a thumbs up. 'Very similar to the anime!'
"What are you doing?" Cynthia asked, raising an eyebrow.
"Ha, nothing! Nothing at all!" Allen quickly waved his hand dismissively before shifting his attention to Gabite.
He nodded in approval, clearly impressed. 'Very handsome indeed.'
"Ga~?" Gabite tilted its head in confusion, clearly wondering why Allen was staring at it so strangely.
"Hahaha, no, no," Allen chuckled awkwardly, quickly pulling a coin from his pocket and offering it to Gabite.
The dragon Pokémon's eyes lit up as it eagerly grabbed the shiny coin, its scales glimmering in the sunlight.
Gabite, being part of the Gible line, was known for its love of collecting shiny items—especially coins, gemstones, or anything that sparkled. It was a little like a magpie, gathering treasures and hoarding them in its nest, and the sight of the shiny coin was enough to make Gabite's day.
"By the way, Allen," Cynthia said, still playing with her Gabite. "What are you planning to do after graduation? Are you going to start your journey right away, or do you have something else in mind? First, you said you wanted to become a professor, then a police officer, then a chef like your uncle. So, what is it now?" she asked, crossing her arms over her chest.
'Ah… the journey… I almost forgot about that,' Allen groaned, rubbing his forehead.
There was still one year left before he, Cynthia, and Caitlin would graduate from primary school and begin their own Pokémon journeys.
Ages 5–6: Kindergarten
Ages 6–10: Primary School
Ages 10–15: The Gap Year
Ages 13–16: University or Vocational Training
The idea behind the Pokémon journey is simple. At some point in nearly everyone's life, they take a break from books and pens to start catching Pokémon, making friends, and exploring their local region on their own.
This makes the Pokémon journey something abstract and broader, allowing everyone to have their own interpretations of what the journey means.
Some even use these opportunities to visit universities or colleges, take shadowing opportunities with different professions, volunteer in the community, explore artistic and sports endeavors, participate in research projects, or focus on a competitive circuit.
Some Pokémon journeys may be short, while others can last longer, depending on the individual's needs and specific arrangements but most trainers spend about three years before returning home either victorious or with valuable experience.
They are generally given a choice of whether they want to become a pro, seek higher education, look for a part-time job for experience, or pursue anything else they desire. The goal is to provide an opportunity for growth and development.
Whether traveling solo or with friends, it's part of a cultural tradition passed down through generations and recognized across all regions. To put it simply, it's an opportunity to gain real-world experience in a specific field before settling down and entering adulthood.
It's essentially similar to the classic journey portrayed in TV shows, manga, and games.
Allen sighed inwardly at her question. Cynthia definitely wanted to become a Champion, no doubt about it.
Caitlin? She was definitely following the same path.
He mumbled unknowingly, "I just want to travel the world..."