Hello, it is the 28th and I am back with a new chapter! This one was enjoyable to write. It's rare that I choose to get into Jessie's head and even rarer to write her interacting with Ash, even if it is via letter! I liked including her personality from the anime and how it would go up against a situation that I headcanon that occurs in Ash's life. I hope you enjoy :3

I own the story and the OC mentioned!

Dear Twerp,

No, I'm not calling you by your name. You're not only lucky that I'm even writing to you, but you're lucky I had to specify which twerp you are on the envelope, so the other twerps didn't think this letter was for them and open it by mistake.

This letter is going to be full of nagging. Maybe. I have to say something. So, you best get ready for an older (beautiful) woman telling you what she thinks. Meowth is sat with me while I write you this. He said that I should say it's an old, nagging, hag telling you what to do but that would get very confusing, wouldn't it? You would think it's your mother writing to you and not me - Jessie.

I guess perhaps that's not the right thing to say to someone you want to listen to you. It's certainly not a good thing Meowth said to me either. I knew what he meant with his words. And he earned a slap before I got back to writing!

Listen, I heard that your dad came to see you. Don't ask how I knew. My husband, Meowth and I might not go spying on you anymore, but we still come to learn things. Me especially. I heard that your dad stopped by. Jerry, is it? Jerry stopped by and you weren't happy, but you went off with him anyway.

Days went by. I think you must have kept on seeing him. Or so I heard. And then I stopped seeing you with him. And that clueless, giddily, infuriatingly happy expression of yours had been wiped off your face and you looked truly miserable. Worse than when James, Meowth and I got you and your twerp of a girlfriend in a cage and called you love birds. Nearly worse than the time you thought you had to leave that Pikachu of yours behind with all the other yellow rats. But not as worse as dealing with your twerpy girlfriends truly bratty behavior.

I'm doing it again, aren't I? I should stop if I want you to listen. But I can't help myself. Maybe I don't want to stop. Maybe I don't want you to read onwards. Maybe I want you to throw this letter away and never look back. Perhaps none of this is my business at all. But it is what it is. I must speak my mind.

I was shocked when I heard that your dad turned up on the doorstep. That can't have been nice for your mom. I heard once – or maybe you told me – he wasn't always that nice to her. He wasn't all that nice to you either. Always leaving you waiting. Always leaving you wondering.

Apart from being shocked, I didn't think all that much of it. I have far too much on my mind with preparing the twins for school, settling Jayden into being a big brother and little Jaxon and how much attention he takes up. And that isn't even mentioning the business or the eldest two and their baffling teenaged problems!

I don't think this is a bit of a teenaged problem for you. Maybe it is. I don't know. Neither of my parents would ever show up on my doorstep. But that's not the point. Or is it?

I was shocked by the sudden appearance of your dad, as I'm sure you were. I didn't think anything of it when you chose to spend time with him, even though I did notice Mrs. Ketchum was a little quieter than usual. Like I said, however, I couldn't help but notice that you looked truly miserable when he stopped being around. And I mean, really miserable. Bordering on sulky and insufferable at times too.

What the hell happened? Not that I care. Maybe it's none of my business. But someone as busy as me must wonder. I don't know what a dad could do to make a grown-up son so upset. Did he buy you the wrong Pokémon cards? Did he tell you that the hat you always wear looks incredibly stupid?

Come on, it can't have been that. My husband and I used to say worse to you daily back in the day and sometimes we still do. Old habits die hard, eh?

Maybe your dad didn't do anything. Maybe it's all you. Did you get overwhelmed by suddenly seeing him days on end after years with no contact at all? Did you decide that he was a man that had no place in your life after you realized that he hadn't even helped you become a man? I could understand that.

Maybe I should just ask someone what's going on. Possibly Gary. He's sure to know. Pikachu would be one to ask as well but then I would need to get Meowth to translate and after him calling me all those untrue names, I'm not sure I want to ask a favor from him! And besides, once he finds out stuff, everybody else will know.

Hardly anything is a secret in this house, is it? But there's some stuff that should be kept private. I guess that's why I'm writing to you. I guess that's why I'm writing to you instead of asking out right. That, and maybe I have no right to anyway.

We might have been united in turns of events in recent years but apart from that, we may be destined to always be on the opposite side of the tracks.

Having said that, though, whether you've even made it this far into the letter (can you even read anyway?) or not, I feel I have to say my bit. I need to say my bit. I must speak my mind.

Ash, I don't know what the deal with your dad is, and, of course, if he's human garbage and treated you or your mother maliciously then feel free to ignore what I have to say. But I just want to say, if I were in your shoes, and if either of my parents somehow came knocking for me – especially my dad – then I would have to give him another chance even if he blew the reunion the first time.

Dads don't get as much credit as moms sometimes and when they are trash, they shouldn't. But when they are good like my dad was – and how maybe your dad still is in spite it all – they deserve another chance.

I would do anything to hear his voice again, even if it were simply to hear him out.

Anyway, that's what I think. You don't have to listen. You can call me a nagging old hag if you want. At least I know I've said my bit.

From,

Jessie.

P.S: If your dad is ever a nasty piece of work then I will sort him out for you because I sincerely doubt you have the muscle to.

P.P.S: If you want to talk dad stuff that's fine too, I guess.

There you go! Thanks so much for reading and I hope you enjoyed :3 So yeah, when Ash is around nineteen years old, his dad makes a sudden appearance back into his life again and that brings all sorts of issues. As if him being absent didn't already cause a fair few! I love the stubbornness of the Team Rocket Trio in the anime and how they act like they don't care about Ash and the gang, but we all know that isn't the truth. And Jessie might try to act as if she doesn't here, but it's clear that she does. After all, why would she bother to write to Ash otherwise? :P Thanks again and I will be back on Wednesday with Pikachu Tales so see you over there!

Amy signing out :)