This was a submission to a Pokeshipping fanart/fanfic contest on deviantART. It had to have a winter/Xmas theme. This is what I came up with. After flopping a similar contest before, I put a bit more effort into this one. Enjoy.
"OK mister smart guy, look where we're stuck now."
"Sorry Misty, I tried my best."
"Ever since Brock left, you've insisted on taking the map, and—"
"Yeah, yeah, I know," said Ash, "I always get us lost."
"Pika pika!" agreed Pikachu.
"And it's getting dark, and it's cold. Ash, I think it's about to snow."
"What'll we do now? We'll die out here."
"Pika!" shouted Pikachu, pointing.
In the dimming light, they could just make out a cabin up ahead. With their remaining strength, they trudged through the grass, hoping no wild Pokémon would jump out and slow them down.
Soon, they were in the cabin, but it was dark and cold and pretty much abandoned. They found a fireplace, but the all the firewood had been used up long ago. They picked out a ration of food from their packs and ate it cold, in silence, feeling miserable but at least grateful for their survival. With no light, not feeling like talking, and nothing else to do, they unrolled their sleeping bags and went to bed.
They couldn't sleep.
"Hey Misty, you awake?"
"Yes."
"Wotcha thinking?"
She paused for a while. Finally, she said, "Nothing."
"Come on, you must be thinking of something?"
"Uh... it's Christmas time, and I was hoping for something better."
"Oh. It's my fault, isn't it?"
"No, Ash."
Silence.
"Well, to be honest..."
"I knew that's what you were thinking," Ash complained. "It's all my fault we're stuck here on Christmas Eve, when we had planned to be at Blackthorn in front of a log fire having Christmas pudding for dessert."
"Ash, please don't blame yourself."
"And instead, we're in the dark, all cold, hungry and lonely. Some Christmas present."
"Alright. Even if I was thinking that," replied Misty, "I didn't want to tell you."
"Why not?"
"Coz I didn't want to hurt your feelings."
"Oh."
There was silence for a while.
"My feet are numb," Ash complained.
"So are mine. You'll live. Where's Pikachu?"
"He's curled up on my stomach. At least that part of me is warm."
There was more silence, for quite a while this time.
"Ash, are you still awake," asked Misty.
"It's too cold to sleep."
"You know, Ash, there is a way we could... oh, I don't know."
"A way we could what?"
"No Ash, it's a dumb idea."
"Well I've got no ideas, so you're one up on me."
"Ash, we've been travelling together for a long time."
"What sort of idea is that, Misty?"
"I know we sometimes... don't get on, but that's only sometimes. Most of the time..."
"I still can't see how that'll fix anything."
Misty paused again. Finally, she said quickly, "We could move our sleeping bags closer."
"How will that help, unless we're actually touching each oth—" Ash gulped. "Oh, is that what you mean?" His heart started thumping.
The silence went on for a long time. It was deafening.
"Ash—", "Misty—", they both started at the same time.
"You go first," said Misty.
"No, ladies first," replied Ash.
"OK, it was a silly idea." said Misty. "Really dumb... and rude. I'm sorry."
"Yeah... I guess it... was," replied Ash.
"You sound... disappointed. I'm sorry if I've upset you."
Silence again. It was now late in the night.
"What if I say that... you didn't upset me," Ash finally piped up.
"Huh?"
"Misty, can you tell me the truth?"
"Have I ever lied to you?"
"No, but you might be hiding something."
"So what do you want to know?"
"Why you really suggested we lie next to each other. I know it's cold, but it's not like we're gonna die."
"Ash, I think you've figured out the reason."
"So what if I say that it's a good idea?"
"I'd be very happy."
"Let's do it then."
They were woken in the morning by the sound of taillows chirping and spearows squawking. Ash stirred first, aware of Misty's head against his chest, her arm around his waist, and feeling warm inside in spite of the cold outside.
They got up, grinning from ear to ear, and had a cold breakfast without a single complaint. They packed up, opened the door, and made their way outside. Pikachu raced on ahead.
"Ash, you know, I was thinking some terrible things last night..."
Ash's smile faded. "To be honest, Misty, I did let you down."
"Don't worry about it. That was the best Christmas Eve I've ever had."
"I hope that's the first of many more like it," replied Ash, his grin returning.
"Pika, pika!" called Pikachu. He was way ahead of them now.
Holding hands, they started running together, on their merry way.