Don't own Naruto
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Keeping her hair short was her way of growing up and letting go of childish fantasies. Every time she looked in the mirror and noticed her hair growing long she'd hear Ino's voice mockingly reminding her how Sasuke likes girls with long hair. On those days she cut her hair shorter with a kunai until someone could do it professionally.
She was desperate to prove she had changed and grown form her younger self. The one that three years ago was worthless on missions and thought Sasuke was the beginning and end of everything.
Sakura's goal was to prove to herself that she wasn't as helpless as she remembered being. She didn't want to prove it to Kakashi, or Naruto, or Tsunade, or even Sasuke. She had seen what the desperation of wanting to prove yourself could do to someone. She had seen how Naruto tore himself apart thinking nothing was ever good enough because he couldn't get acceptance from every person in the village. It hurt her to see Naruto brush aside her compliments or Kakashi's grudging words of praise or Iruka's kind encouragements or Tsunade's soft words of love. It didn't matter to Naruto that Sasuke had claimed him as an equal. All Naruto saw were all the people who had yet to acknowledge him.
After watching Naruto work himself into a frenzy for years Sakura had decided that the best person to please was herself. She was no longer going to push herself for someone else's standards.
And that is how Haruno Sakura grew from a child to a woman and lived her life happily.
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Today I am dirty. I want to be pretty.