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Sasuke Uchiha was perfectly content with what he had. He lives a comfortable life, has nice friends, and gets good enough grades to get by to graduate (he could do without the annoying fan club though). Every thing was in place and as it should be except that one fateful day he had lost a stupid bet.

His punishment seemed simple enough - make a girl fall for him.

He would then soon realize that being "content" was a lot different from being truly "happy".

Now, would he win this silly little game?

NOTE: NOT a book of One shots; Rewrite of original; Modern AU; High school AU; Dark Themes; Foul Language

I do NOT own Naruto.