Thank you to everyone who reviewed so far! I hope you enjoy this next chunk:)

XO

"Why do yous want us to be writin' love lettas?" Meowth asked Jessie as he stared at the blank sheet of paper in his paw.

"It's called role-playing, Meowth. You are pretending to be the twerp. I already told you what to write. Don't be difficult," Jessie chided.

"I think it's fun," said James.

"I tink it's lame and borin'."

"Do you have a better idea to take advantage of this opportunity?" Jessie asked.

"No…"

"Their reactions may be quite hilarious to watch," James said happily

"I can't tink like a twerp. I'm an intellectual."

"Wobbufet!"

"Shut it, yous."

"I believe in you," James told Meowth. "Ash isn't that complicated."

"Who's Ash?"

"The twerp!" Jessie exclaimed. "Ummm, right James?"

"Yes. He's the chief twerp," James replied.

"Right…" said Meowth.

"These letters will throw them all off and give us a good laugh," said Jessie. "And as we are laughing, we'll take advantage of their lowered spirits and grab as much of their Pokémon as we possibly can!"

"Wobbufet!"

"Read this and let me know what you think," James said as he handed Meowth a letter.

Meowth cleared his throat and read:

"Dear Misty,

It's beena while since yous and I got together alone. I think you and I should meet up and get all cozy 'n stuff in dat dere clearin' in de Viridian Forest near yere house. It should be tommorra at night 'bout ten and please don't call 'cuz my phone ain't workin' too well nowadays. And dis is a private matta so please don't bring no Pokémon wit yous to our meetin'.

Lots of kisses,

Ashley."

Meowth glanced over the letter, handed it to Jessie, who read it for herself, and then she laughed. Meowth laughed too. James snatched the letter back.

"Why are you being so rude?" he asked defensively.

"Cuz you ain't no good at writin'," said Meowth.

"It's not my writing that was bad, it was the way you read it!"

"It's fine, James. At least it looks like something Ashely would write," said Jessie. "Here is mine:

Dear May-bae,

I have been in love with you ever since we first locked eyes! There is nothing I love more than your not-so-annoying peppy attitude and decent sense of style. I think we should meet in the Viridian Forest in the spot near my house tomorrow night at ten. Please don't bring any Pokémon with you; I want this to be private and special. Also, my phone is broken and so is my email so don't try to message me before then.

All my love,

Ashley."

"Dat's good," Meowth grinned.

"We can have our spy cameras record their interaction in the woods and in the Pallet House and in meantime we will steal all of their Pokémon," said Jessie. "We'll get tons of rare and powerful Pokémon and a show. Plus, our plan is fool-proof!"

"I wanna read my letta next," said Meowth. "Ahem:

"Dear My One True Love,

I loved yous eva since weeze were little kids playin' in school and whateva. I have been jealous of yous foreva and de truth is dat I loves you lots and I'm havin' trouble controllin' it since now I'm a teen and all dat. Please come (no pun intended) to de Viridian woods in dat nice little clearin' not far from yere house and my house. Please don't call cuz my phone broke just come and don't' bring no Pokémon neiter.

Love,

Your Ashy-Boy."

"This is brilliant," Jessie said as Meowth proudly folded the letter.

"And hilarious, though I do feel bad," James sighed. "What if Ash is truly in love with one of them?"

"It don't matta," said Meowth. "We are de bad guys, rememba?"

"I remember," James mumbled.

The team wrote several more letters each and then called it a night. They didn't sleep well though; they were all looking forward to seeing their creative plan reach success.

XO

It was eleven the evening of February the 13th and Ash was staring at his computer screen with a dull look on his face.

"Pikachupi? Pi~?" Pikachu asked as he nudged his trainer.

"Ssssorry buddy," Ash sighed as he petted the top of Pikachu's head. "I'm just trying to figure something out."

"Pika?"

Pikachu scanned the computer screen. It was some article with a heart-shaped logo next to its title. Pikachu then opened the notebook resting on the ground near Ash's feet. The Pokémon picked it up and tried reading. He couldn't understand the words in their written form, but he did recognize the pictures and the tally marks under them.

"Pikapi~?"

"Hey! It's not what you think," Ash said as he snapped the book shut. "It's not like I am rating them…"

"Pikachu!"

"Okay, let me explain…I just gotta gather some thoughts."

Ash took out his phone. His scrolled through some pictures; some were recently taken, some were old and had to be converted into a different format. Pikachu was patient.

"If I tell her I like her, then it might ruin our whole group friendship," Ash started. "Because Misty is friends with May, Sakura, and Duplica, May and Duplica are friends with Dawn, Dawn is friends with Iris, Iris is friends with Serena, Serena and Misty are also friends, and both Serena and Misty are friends with Mallow, Lillie, and Lana—and that's just the girls. I also have to worry about Tracey, Brock, Richie, Max, Drew, Cilan, Clemont, and my mom probably invited my not-so-friendly rivals…like Paul and Gary and maybe Harley..."

It was clear that Pikachu still didn't understand.

"Like, what if Misty likes-likes Tracey? Or what if Misty likes-likes Gary or Brock or Tracey? This stuff is all so frustrating. This is why I like Pokémon so much; Pokémon don't make my head hurt."

"Pika?" Pikachu asked as he pointed to a picture of Serena. Ash instantly blushed.

"Ummm yeah, so at least I know she likes me…" Ash mumbled. "And I like her too…"

Ash put another tally mark next to Serena's picture. Pikachu cocked his head to the side, indicating that he found the action nonsensical.

"I'm weighing the pros and cons," said Ash. "It's not about who I like the most, it's about…like…okay, so I was thinking that maybe it would be about which person I would ask to…to…Well, it's Valentine's Day, and what if someone tells me that they like-like me or they ask me who I like-like and I can't avoid the question? Like, should I make it easy and say that I like Serena, even though Clemont told me that he likes-likes her? If Serena asks me if I like her, do I say 'yes' or 'no'? What if May asks me out? Brock told me she likes me…but he also said that about Misty…and Brock and Misty get along better than me and Misty do, and they are both gym leaders and closer in age…it's so confusing. Life was easier before sixteen."

Pikachu pointed out that though Ash is numerically sixteen, his mannerisms and use of vocabulary put him closer to age twelve. Pikachu put his paw over the person he wanted Ash to choose.

"No! I can't do that!" Ash said as he flipped the picture down.

"Pikachu Pi!" Then why was it printed out along with the others?

Ash didn't have to guess what was going through the Pikachu's mind. He decided to numb his mind with a game of Tetris with his computer on Flux mode, ultimately knocking him out before the clock hit February the 14th.

XO

Thanks for reading. Please review if you have the time:)