Jessie:

This one was a long time coming, might not be the best one due to the fact that I don't want repeats in each of the stories, this one will not be overly romantic but more of a friendship one .

Ash: 17

Jessie: 22


Ash in a cave with a member of Team Rocket his arch nemesis, the two glared at each other the entire time while waiting for their friends to help them out of the situation, it had been a few hours since the cave in the left the two trapped, the red haired member of Team Rocket sat there not even moving an inch.

"Once we get out of here, I will make sure that I will take Pikachu from you," she said with a sinister smile.

Ash shrugged his shoulders and shook his head at the same time, "and you will fail like always," Ash retorted calmly before turning around.

Jessie puffed up her cheeks and turned away in frustration that the trainer came up with a return to her chance to capture Pikachu, "well then, I will make sure you're still trapped in here," Jessie replied in anger.

Ash let out a quick sigh of disappointment before turning his gaze to Jessie, "Jessie, can you at least pretend to be friendly?" Ash asked in anger.

Jessie spun around and looked at Ash for a moment, "alright then, let's play Truth or Dare, you first twerp," Jessie replied with a sly smirk.

"Alright, Truth," Ash called out with a grin.

Jessie let out a big smile on her face before saying a word, "who do you have a crush on?" Jessie asked with a wide grin.

Ash's face turned red at the question, he tried to hide the deepening red color of his face, "that doesn't count!" Ash yelled out feeling flustered at the question that Jessie asked.

"You did say truth," Jessie retorted, "come I will keep it a secret for you," Jessie promised while her hand was hidden behind her back, "come we're friends right?" Jessie enquired while crossing her fingers.

Ash gulped as his deep red shading left his face, "I….. um have a crush on May," Ash confessed with the blush starting to deepen again, Jessie burst out into laughter but sort of respected Ash's reply, "not funny this is serious," Ash told the member from Team Rocket.

Ash puffed up his cheeks as his deep blush disappeared, he looked at Jessie for a moment, "your turn Jessie, you can trust me," Ash said while crossing his fingers behind his back.

"Alright I choose dare," Jessie declared with confidence, "if you pull anything funny, I will tell May your secret!" Jessie yelled in anger, Ash laughed at the threat that was being presented to him, 'not that I will be a secret for long,' Jessie thought while looking at the wide grin coming from Ash.

"Dare right, are you sure about that?" Ash questioned in a cheeky tone.

Jessie started to get angry at the tone of the trainer, "I am a hundred percent certain!" Jessie replied in anger while witnessing the expression change on his face.

Ash now had a serious expression on his face, "I dare you to kiss James once we get out of here," Ash dared Jessie.

Jessie got up with her fists clenched, "how dare you, I will never kiss that loser!" Jessie screamed out after punching the trainer.

Ash got back up and cupped his face, "come on, it was dare, you have to follow through with it, rules of the game," Ash explained with a cheeky grin, suddenly a light started to shine above them until a female with shoulder length brown hair peered in, "May, nice to see you again," Ash called over to the coordinator. Ash looked over to Jessie for a moment, "one more go while they help us out, I choose dare," Ash said as the light started to get brighter.

Jessie looked at Ash and thought of the perfect revenge for the trainer, "I dare you to kiss May," Jessie retorted with a sly grin, "and there is no way you can get out of this dare, friend," Jessie explained, Ash started blushing like crazy knowing that he couldn't get out of the dare, "while confessing you love to her, you have to Ash, otherwise I will steel Pikachu the moment I get out here," Jessie explained with a chuckle, "I choose truth."

Ash thought seriously for a moment and came up with a question that would be best suited for the moment, "do you seriously like working for Team Rocket?" Ash asked calmly.

Jessie sat there in shock and started to think about the question that Ash asked her, "Team Rocket is a tradition in my family, but there are days where I wish I could do something else," Jessie professed calmly as James extended his hand out to pull Jessie to safety

May extended her hand out to Ash to bring him to safety, after being pulled to safety the four people looked at each other for a moment, Jessie was the first to turn away, "let's go, I don't feel like capturing Pikachu today," Jessie explained as she walked away from the battle much to the shock of James, Meowth and May.

Ash smiled at the situation and turned away with neither of them fulfilling the dare they set themselves, Ash looked over his shoulder at the same time as Jessie, they nodded at each other respectfully while walking in opposite directions, 'one day I will fulfill that dare Jessie,' Ash thought with a proud smile while turning his gaze back to May.

'I promise to you my friend that I will fulfill my dare that you set me,' Jessie thought with a grin while walking in the other direction.


Remember this one was more of a friendship story and less on romance, but this one might get a sequel later in the series, please read and review this short story and have a request at the ready.

Next story will be between Ash and Roxie, followed by either Fennel or Cynthia.

Please have a look at my other stories and prepare for the next part of the Evolvers Story at the start of the new year, the story is called The Evolvers: Elements