(A/N): Pokemon are almost non-existent as I wanted to focus on character development. In this story, they are treated as normal animals and will probably be only mentioned or used as part of literary devices.

This fic does not only contain AdvanceShipping, it is about AdvanceShipping so here's a warning, this fic might cause shipping overdose on those who are faint of heart.

Chapter 1: First Day

Ages

Ash: 5

May: 4

It was a peaceful and warm Monday morning in the small town of Littleroot. The sun was shining brightly and the chirping of Tailows were heard. It was also the first day for schools in the tropical nation of Hoenn, where Littleroot was located.

Inside one of the houses in Littleroot, a young boy of 5 with jet-black hair and auburn eyes was hiding inside his room, trembling, while his parents were convincing him to go to school. The young family of 3 has just relocated last week from Pallet Town in the faraway nation of Kanto.

"Ash! There's only 30 minutes left before the school starts."

"B-b-but mum I'm s-scared! I don't know anyone. What if they don't like me?" Ash couldn't resist letting out his tears.

His mother, Delia, opened the door and embraced him in a warm, comforting hug. His nervousness never dissipated completely, but it was slowly disappearing as Ash enjoyed his mother's hug. She put her mouth near his ear and whispered. "Don't worry. You're a sweet boy. I'm sure everyone will like you." Feeling defeated, Ash walked off his bed and walked towards his desk to grab his bag before walking downstairs with his mother to see his father Giovanni slowly drinking his coffee and reading the newspaper while waiting for him to be ready. Noticing Delia and Ash at the stairs, Giovanni folded the newspaper gently and finished his cup of coffee. Seeing the expression on Ash's face he lowered his body until his head was level with Ash's.

"Son, it's going to be alright. I understand how nervous you are. I was just like you back then, except worse. Heh, my mum even has to carry me to school while I was punching her shoulder, how embarrassing." Giovanni let out a small laugh as he reminisces his first day of school. "But it ends well after the first day because I made a new friend. She has beautiful yellow eyes and long reddish-brown hair. Does she seem familiar, son?" Ash glanced at his mother and noticed that she looked exactly like the friend his father described. He soon put two and two together and deduced that the new friend his father talked about was his mother. Noticing that Ash has deduced his clue, Giovanni grinned and spoke in a teasing tone. "Maybe your first friend there will be your future wife!" As he winked and teased his son his laughter couldn't be held back and this one was far louder than the previous one. Seeing that time was running out, Delia grabbed her husband's right hand and touched his watch. Giovanni's laughter died out and he gestured Ash to get outside, which he complied hesitantly. His nervousness grew slightly as evident from the blush on his cheeks after Giovanni teased Ash about his future wife. As Giovanni closed and locked the door, a metallic box could be seen on the dining table but no one noticed it.

While on the 10-minute walk to his school, Ash was mute, simply enjoying the beautiful and lush scenery as his parents were having a conversation speculating on how Ash's life in school would be like. Still nervous and smaller than his parents, he walked slower than his parents which went unnoticed until they realised that Ash was nowhere besides them. They turned their heads to their backs and found Ash absent-mindedly walking. They yelled at Ash to make him move faster and each of his hands was held by one of his parents to ensure that they walk with the same pace. When they arrived at the hallway inside the school, Giovanni took a paper out of his pocket, a letter from the principal showing where Ash's class was. As they were in front of Ash's class, his nervousness resurfaced. He was trembling and hid behind his parents, wrapping his small arms around his father's large and strong legs.

The class has around 10 students and 1 teacher. Some were running around chasing each other playfully while the quiet ones were simply sitting on their seats waiting for the day to start. The teacher smiled at the sight of her students. She cast a glance at the wall clock suspended on the back of the clock. It was time for the class to start. She clapped her hands to attract the student's attention. They immediately halted their activities and ran to their seats. "Okay class today we have a new student from the faraway land of Kanto. There might be differences between Kanto and Hoenn so he might not be familiar here. Please be nice to him!" The class nodded and the teacher opened the door to reveal Ash, Delia, and Giovanni with Ash still clinging on to Giovanni. The three of them walked towards the centre of the class with Giovanni walking awkwardly as Ash was still holding to his legs. This earned him a loud laughter from the class and even a small chuckle from the teacher. The teacher went closer to Ash and said, "Don't be shy. Why don't you introduce yourself?"

Giovanni struggled to release himself from Ash as he shook his leg but did it successfully. He gave Ash a pat on his shoulders to encourage him. After several seconds of silence, Ash mustered the courage to speak. "H-hi. My n-name is Ash K-ketchum. I am from P-pallet Town in Kanto. P-please be nice t-to me." Delia and Giovanni excused themselves from the class and left.

When they're outside the school Giovanni spoke, "You see there's only one empty seat in the class and look who's sitting next to the empty seat." Delia only saw the class briefly but saw a girl sitting next to the chair. Giovanni continued, "Though only time will tell that my prediction is correct or not."

Inside the class, the teacher smiled at Ash before taking his hand. "Good morning Ash. Call me Ms. Winona. For where you'll be sitting…" Winona looked around the class to spot an empty seat. "… there's an empty seat next to May." She pointed the table where a blue-eyed brunette whose hair reached the shoulder was sitting and an empty chair.

As Ash approached the chair he spoke nervously. "Hi. I'm Ash. Do you mind if I sit here." He earned a giggle and a smile from the brunette.

"Silly! You already introduced yourself. My name is May and just sit next to me. I don't mind." As Ash sat next to May she offered him a handshake, which he nervously returned. May continued giggling as she finds Ash's nervousness cute.

For the first day Winona let the students do anything they want as long as they don't disturb the class. Some were drawing while some were making jokes. Meanwhile, May was talking to Ash, wanting to know about life in Kanto. Ash started off nervously, not being used to telling stories but soon felt comfortable, enjoying May's presence. After Ash finished his story, he feels like it's his turn to ask so he asked May about her life in Hoenn. She told him her story happily. Ash found out that it never snows in Hoenn due to its climate, much to his disappointment, while May found out that Kanto was more technologically advanced than Hoenn, not that it mattered much to Ash due to his young age.

Soon, it's time for recess. Ash was starving and as Winona gave the signal for recess he became revitalised and rushed to his bag to get his meal. His mood went down after searching through his bag. Must've left it at the table. He thought to himself. He just put his head on the table and tried to sleep to pass off the time. May noticed that Ash wasn't in the very best mood so she gently tapped his shoulders. This woke Ash up.

"What's wrong May?" Ash's voice was a little loud as he was startled. However, Ash's loud voice did not affect May at all. Her face showed concern.

"That should be my question. Why are you not eating?"

Ash rubbed his head sheepishly and refused to give May an eye contact. "You see this morning I was very nervous about going to school so my parents rushed me. There was only 15 minutes before it starts so I left it on the dining table."

May laughed and giggled before handing Ash her meal. This surprises Ash a lot. A person who he just met a few hours ago was willing to share her lunch with him. He was hungry but he did not want to trouble people. "Are you sure? It's your food after all. It's just hunger. I mean when I go home I can eat."

In response, May put a finger in front of Ash's lips gesturing him to be silent. "It's okay. Mum made too much. I couldn't possibly eat all of them. Here I'll split it into two." May cut her sandwich into two equal parts and handed one of them to Ash. Ash thanked May and devoured his sandwich. May tried to hold back her laughter seeing the extent of Ash's hunger.

After May & Ash finished their sandwiches Winona clapped her hands again. "Time to go outside kids. You have 30 minutes. You can do anything at the park but make sure you stay at the park." They yelled in agreement and ran to the park outside the school building. Ash chose to use the seesaw and May followed Ash. It was obvious that both of them enjoyed their time together. By now there was no trace of the nervousness that Ash displayed earlier.

After a while Ash became bored so he decided to tease May. "Catch me if you can May!" He hopped off the seesaw and ran away from May but she wasn't going to lose.

"I will get you Ash!" She yelled in her loudest voice before she ran. The speed in which she ran was simply ridiculous. It was not normal for a 4-year-old to run with that speed, the speed that could match most 10-year-olds. Ash was simply running around the school building but after a minute or two May caught on to him and tackled him. Ash then felt a pair of arms around his waist and felt it squeezing him. "I got you now, Ketchum!"

"A-ah-ah. T-that h-hurts May." Ash was in pain but her face showed no signs of malicious intent, only playful intent. Seeing May's intention as innocent Ash could only laugh with May. Winona saw May tackled Ash to the ground and she ran to them, as she was afraid that a fight would break. However, their face only showed laughter and smiles. Winona realised that they were only playing around so she left them alone.

When playtime was over, Winona asked the students to walk back into the class, which they happily complied. For the next hour, Winona taught the class basic arithmetic with marbles. She was surprised by both Ash & May's competence in the subject. While the other students were struggling initially, they understood it immediately. I see a couple with bright future. She thought to herself.

The first day of school for both Ash & May was finally over. One by one the students were picked up by their parents but after 30 minutes there are 2 students left. Winona looked at them with concern.

"Where are your parents, Ash and May?" Both of them shook their heads non-verbally telling Winona they don't know. She proceeded to her desk and took a notebook containing information on how to contact each of the student's parents. First she contacted Giovanni.

"Good afternoon, Mr. Ketchum. This is Winona, your son's teacher. I apologise for disrupting you but it has been 30 minutes since class has been dismissed and your son has yet to be picked up."

"He-he-he. My bad. I was just getting acquainted with my new neighbours and it seems that I've lost track of time. Can you tell Ash I will be there in about 20 minutes?"

After Winona disconnected her call with Giovanni she proceeded to dial May's home. After a minute the voice of a woman, presumably May's mother could be heard on the other hand. "Good afternoon, this is the Maple household. I'm Caroline. How may I help you?"

"Good afternoon Ms. Maple, my name is Winona and I am your daughter's teacher. 30 minutes have passed since class has been dismissed and I was wondering, why no one has yet to come pick up your daughter."

"My apologies. I have just returned from grocery shopping several minutes ago. Would you please tell May that I'll be there with her father in about 20 minutes?"

After the call had ended, she told both Ash & May that their parents were going to pick them up in 20 minutes and they are free to do anything they want in the class given that the class will still be tidy afterwards. They nodded in agreement and Ash took a sheet of paper from the cupboard while May took a set of colour pencils from the shelves. They spent the 20 minutes drawing while laughing, cherishing the moments they spent with each other. The 20 minutes have passed and both sets of parents arrived simultaneously. Delia and Caroline ran to each of their respective children and hugged them while Giovanni and Norman, May's father, waited patiently near the door.

"Sorry for forgetting you. We promise it'll never happen again." Both mothers expected their children to be sad or angry but their response surprised them.

"It isn't all that bad. Ms. Winona's been with us all along and it's fun to be with Ash/May." Both children said in unison.

While the mother's and the children were with each other, the fathers took their time introducing themselves. Giovanni took the initiave and offered his right hand to Norman.

"Nice to meet you. I'm Giovanni Ketchum. It seems that our children have become friends so there's no reason why we should not."

"Nice to meet you too. My name is Norman Maple. You stole my line, you sly fox! Guess great minds think alike, eh?" Norman smiled at Giovanni and offered his hand and they shook hands.

"By the way, we need to keep in touch if we want to be friends. Here's my card." Norman accepted Giovanni's card and gave him his own.

Delia and Caroline held their children's hand and they went their separate ways. "See you tomorrow!" They yelled to each other before none of them were visible to the other anymore.

When the Ketchum family arrived at their house the first thing Ash does was running to the couch and unwinding after a long day. Giovanni and Delia followed Ash to the living and began questioning his first day. Giovanni started the conversation.

"Told you son. You'll be fine after the first day. And see, someone already likes you. Norman's daughter, who's her name again?"

"It's May and you're right dad it gets better!"

Delia decided to join the conversation. "What did you do with her today?"

"Nothing much. We just talked about Hoenn and Kanto and played see-saw. Wait! I got off the see-saw and made her chase me. Trust me I don't want to do it again. She ran with a speed that could make a Ninjask green with envy and after she caught me she tackled me and hugged me harder than an Ursaring could. But she's a very sweet girl, I left my lunch at home and she shared her sandwich, I didn't even ask. She said her mum made too much but from the size of the sandwich I'm not so sure. I don't know why she would do that."

Giovanni and Delia couldn't believe from what Ash had just said. It was obvious to them that the brunette liked their son but they couldn't have expected that it would have been to this extent. He whispered to Delia so that Ash couldn't hear it. "I don't believe we went this far on our first day. All we did was just talking with each other." Giovanni's face turned stern and serious before he faced Ash. "So son, would you mind telling me when May and you will be wed?" He broke out of his intimidating look before bursting out into laughter, enjoying his joke at his son's expense.

"Daaaaaaaaad!" Ash yelled out in embarrassment his face clearly red, even more than the one that happened in the morning. Delia, having enough of her husband's teasing, scolded him. After calming down, Giovanni walked to his room to take a nice, warm bath while Delia went to the kitchen to make tea for the family.

Meanwhile Ash was still on the couch feeling exhausted, thinking about his day with May. What a way for a first day of school. That was his last thought before he fell asleep with a smile on his face.

(A/N) This chapter could be read as a one-shot but I'm planning to make this a chapter fic. It shows the relationship between Ash & May through different ages. I'm planning to make around 10 chapters for this story. The last chapter will have Ash & May aged about 25.