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It was mentioned in episode 1 of Ufotable's Fate/Unlimited Blade Works that Tohsaka used to go to the archery dojo to watch someone. Was she secretely watching Shirou because she had a crush on him (but how?) or was she looking out for Sakura? Did Tohsaka know of Sakura's feelings for Shirou?

Gao
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I would assume it was because of Sakura. She knew full well of the dealing between her father and the Matous, and it's revealed in Heaven's Feel that despite Sakura's changed appearance (due to the brutal abuse Sakura suffered), she still knew Sakura was her sister.

For comparison's sake, this is how different Sakura looks before and after she was adopted.

(Left - Pre-adopted Sakura. Right - Post-adopted Sakura)

Also Rin turned up at the dojo after Shirou left, so we can rule him out. The only other person in the club Rin has a relationship with is Ayako Mitsuduri, so it could be her. Nevertheless, Rin cares very deeply for Sakura despite the deal between their families, and I think I remember her mentioning she could only watch Sakura from afar and would have rather protected her if she had the chance.

nhahtdh
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Memor-X
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    According to this [post](http://randomc.net/2014/11/16/fatestay-night-unlimited-blade-works-06/comment-page-1/#comment-1588369), Tohsaka stopped going to the dojo when that someone stopped going there. Was Tohsaka watching over Sakura to protect her from her abusive brother Shinji, or was she secretly observing Sakura and Shirou and hope they develop into a relationship so Sakura will be happy, and at the same time hope they don't because Tohsaka also has some feelings for Shirou since the bar jump event? – Gao Jan 28 '15 at 05:48
  • @GaoWeiwei i can't remember if Rin mentions she too saw Shirou at the Bar Jump Event but i'll double check the prologue to see if Rin mentions if she stopping going after Shirou's accident but i assumed she still went there on occasion for Sakura's sake. – Memor-X Jan 28 '15 at 06:02
  • however being a serious Magus of a prestigious family she has to select a future husband who will allow her to have a child that will carry in the linage and in the prologue she mentions that she knew one other family who could enter the war but their heir was no good (to which i assumed she meant Shinji sine Kiritsugu was an illegal Magus in the city having to contacted her as the Second Owner) so she wouldn't develop feelings for him too deeply before finding out he was a Magus – Memor-X Jan 28 '15 at 06:03
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    +1, I also assumed it was because of Sakura. I got the vibe that Rin was initially interested in Shirou only because of how close he was with Sakura. – Torisuda Feb 01 '15 at 00:28
  • According to episode 22 of Fate/Stay Night: Unlimited Blade Works, Rin saw Shirou practising bar jump one day after school, which she kept as a secret. I'm convinced that besides Sakura, Tohsaka also secretly observed Shirou at the dojo, wanting to know more about someone she admired. – Gao Jun 06 '15 at 18:32
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    @Gao I have just went through the prologue again, Rin was invited to the Dojo by Ayako when Rin arrived at school earlier than usual. she also mentions she has 3 acquaintances there, one is Ayako and she says one you should actually call an acquaintance but doesn't name who (could be Shinji but not an acquaintance could also refer to Sakura since they are sisters). she also mentions she first became friends with Ayako after watching the dojo from afar though I can't confirm when this was in comparison to when she first saw Shirou and when he quit the dojo – Memor-X Jun 08 '15 at 08:48