Make You Look Better
The first time Sakura went on a date with Naruto (if only for old times' sake), she dressed up and asked Sai how she looked. Not because she expected anything other than the usual, but because she hoped to learn to read Sai's response.
Sai scoffed and looked at her with distaste, "Ugly. As always."
She just smiled and punched him. Force of habit, she thought secretly to herself.
No matter what Sai said, she had a good time. They ate something other than ramen and talked about Tsunade, and Kakashi, and Jiraiya, and all their friends. But mostly they talked about Hinata because Naruto had finally learned to interpret her shy stammering.
The first, and only, time Sakura had gone on a date with Neji (because Tenten was going with Lee and Sakura was 'around') to the Summer festival, she put on her best kimono and asked Sai how she looked.
He gave her the same look of distaste and narrowed his eyes at Neji as he passed by. "Uglier than usual."
Her eye twitched briefly and she broke his nose, then healed it with a sigh.
In any case she enjoyed herself. She found Neji was not so bad and Tenten wasn't the only one with excellent aim. She went home with a smile and a new stuffed dog.
The first time Sakura accepted Lee's invitation to dinner (his prize for having run 500 laps around Konoha), she dressed in her new skirt and asked Sai how she looked.
She got the same look as before and his answer remained unchanged. "Still ugly."
This time she left him with his head in a wall.
But she laughed with Lee and promised to have lunch with him sometime. They walked home and she found out who Lee's new love was.
The first time Sakura broke down to him she was wearing a stained medical cloak and, after her sobs died, asked Sai how she looked.
He looked at her oddly, then smiled. "Ugly."
But Sakura had learned to read him and smiled back.
"Ugly. But I'll make you look better."
A.N.- Why Neji? I have nooo clue. My thought process just went; Sai... Sakura... dates... ugly... NEJI!! ...wait, what?
I had to do it.