Disclaimer: I don't own Descendants

Jay never lost a bet or backed out of a dare. Ever. His whole 15 years of life.

After skipping school he headed toward an alley, knowing Mal will probably be mad that he skipped without her. That's when he ran into Harriet Hook. Turquoise and all.

"Hey, you." She called to him.

"Yes pirate?" Jay flirted while walking to her.

Harriet giggled but soon regained control of herself. "I saw you walk'n on my turf. You're in debt now."

The memory came back to Jay when a few days ago he was stealing a necklace from the outpost. Or in other words, from Harriet Hook's turf. There was one rule to stealing. Don't get caught.

Jay leaned against the wall, "And if I did?"

"You're in debt to me. Like I said before." Harriet answered. "I know you won't admit it, but we both know you did it."

Jay kept on a poker face. "How would one get out of debt eh?"

Harriet smirked. "I am so glad you asked."

Jay simply stayed put and showed no emotion.

Harriet laughed empty-heartedly. "You can get out of this little debt, if you take me up on a bet."

Jay was puzzled. No one ever won a bet against him.

"You're on." He stuck out his hand for her to shake.

"Don't you want to know the consequences when you lose?"

"You're dreaming." He replied as they shook hands roughly.

Harriet crackled. "The bet is, that, you, can't steal a specific girl's heart."

Jay smirked. He's been stealing heart's since he could walk. "Which girl?"

Harriet crackled again. "Mal's"

If Jay had been drinking something he would have spit/sprayed it out like in the movies. He can't do that! Mal was his fri- partner in crime. He doesn't like her that way. He couldn't. She's like the sister he never had.

"And if you don't get her heart in about... Oh two weeks? You become a slave to my ship."

"It's on Pirate." He replied calmly.

She giggled and ran off.

Jay slumped into the shadows. This might be the one bet he loses, with the highest stakes at play.

Mal's POV

That son of snake! Leaving me to sit through class by myself.

Mal was not in a good mood. Someone had stolen her necklace, she believes it was Jay, but she decided to give him the benifit of doubt. She knew it was him. It had to be. Who would steal from her? Certainly not these no-good-stupid-citizens.

She completely spaced out in class. Lady Terminal turned her back and Mal took the opportunity to sneak out.

As she wandered the streets she saw a familiar flash of turquoise leaving an alley. She slid her way to the alley and saw

"Jay?"

"Oh! Hey Mal." He said with his signature smile. The one that makes all the girls swoon. But Mal wasn't like other girls.

"Give me my necklace." I said with my hands on my hips.

"What makes you think I have it?" Jay asked.

"Other than the fact that it's hanging out of your pocket? Your name is Jay." I said.

Jay chuckled and grabbed the necklace... and threw it into the sewer!

I glared at him. "You're getting that."

He chuckled. "What's my name?"

"Jay."

"Say it"

"Jay"

"Say it."

"JAY-JAY GO GET IT." I screamed, annoyed at him for making me use his nickname.

He smiled and grabbed the necklace. He came up behind me and moved my hair to the side.

I flinched at the sudden exposure of my neck to the cold air. And also for the exposure of my neck at all. You don't let others on the Isle be close to weak spots. I could hear him breathing down my neck as he clasped the chain on. The cool metal felt nice against my warm skin. He moved my hair back and stood in front of me.

"What was that Jay!" I yelled at him.

He just laughed and winked at me before he left.

Jay's POV

I can't believe I did that! Mal... Mal is my... dare I say... friend. Nothing more. Nothing less. Two weeks. Two weeks to make my best friend fall in love with me. My cold-hearted best friend.

I walk to the market and steal some things before going home. I keep on thinking about the bet. That stupid bet. I should've been more stealthy when I stole that necklace. My father will not be happy to hear about this. That's why I won't tell him.

Mal's POV

THAT JERK!

"Ugh!" I kick a rock and it lands in a puddle. It splashes a LOT of people. That lifts my spirits a bit. I just don't know why...he always winks at me. Why... why did this one feel different. Like... like he was flirting with me? Nah.

I finally realize my train of thought and remember. It's Jay. Crazy Jay-Jay. I have nothing to worry about.

Those of you who are/were reading my After Oh no, Oh dear one-shots, I apologize. I was working on one of them when I lost my inspiration. I am currently trying to get it back though. And yes, to those of you who haven't read the books (YOU NEED TO! THEY ARE AWESOME!) Harriet is the oldest of the Hook siblings... I think. She's the daughter of Captin Hook.