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At many points in the story, when Dumbledore asks Harry something, he gives him a piercing look. It makes me wonder if that is Dumbledore using Legilemency against him. Is he?

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11  
I can't remember anything in the books to suggest that. I thought it was the kind of "piercing look" I used to give my students when I wasn't sure they were telling the truth. – Matt Gutting Jul 29 '14 at 12:27
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@MattGutting Harry admits that Dunbledore sees through him in a way even Mad eye's magical eye couldn't. Just my thought – Hashir Omer Jul 29 '14 at 12:29
    
@HashirOmer - yes. I felt the same way with some of my Muggle teachers. – DVK-in-exile Jul 30 '14 at 18:00
up vote 31 down vote accepted

He certainly seems to find some information when giving Harry these 'piercing looks', but he still doesn't know about Harry hearing the basilisk in the Chamber of Secrets, so I would say no; he's just extremely smart, so he makes some educated guesses as to what Harry is thinking.

I would also say that Dumbledore would feel it is rude to intrude on Harry's thoughts with legilimency, which is likely the reason he gives Harry plenty of opportunity to tell him his thoughts of his own accord. Harry's free will would factor greatly into Dumbledore's decisions.

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Good point about the basilisk – Hashir Omer Jul 29 '14 at 12:56
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Dumbledore's piercing looks typically are used when hes determining whether hes being lied to or not, Or if something is being withheld from him. legilimency is a very invasive spell as we find out when snape uses it against Harry so we know for sure hes not using it. – Himarm Jul 29 '14 at 13:22
    
@Himarm:Or maybe you just experience it in another way when you KNOW that someone reads your mind?! – gruntswilldie Jul 29 '14 at 13:28
    
I seriously doubt that Dumbledore would use such a spell on Harry, he trusts people a little too fully remember, so I don't think he would have ever used it on too many people, certainly not people so close to him – ZenLogic Jul 29 '14 at 13:30
    
I dont think you could say Dumbledore trusts people to fully, he trusts people enough where it counts to get the job done. Other then his betrayal by grendelwald you see he never over extends his trust. Also Dumbledore will do practically anything to achieve his goals, and if he felt he needed to force Harry to talk... he would force Harry to talk. – Himarm Jul 29 '14 at 15:22

No.

Harry would know if legilimency was being used on him, as when Snape used legilimency on Harry (all emphasis added):

“Liar,” said Snape. Harry’s throat went dry. He knew what Snape was going to do and he had never been able to prevent it. …

The bathroom seemed to shimmer before his eyes; he struggled to block out all thought, but try as he might, the Half-Blood Prince's copy of Advanced Potion-Making swam hazily to the forefront of his mind.

And then he was staring at Snape again, in the midst of this wrecked, soaked bathroom. He stared into Snape's black eyes, hoping against hope that Snape had not seen what he feared, but –

Here, what Snape was trying to see "swam [...] to the forefront of his [Harry's] mind", so Harry was an observer as well as Snape.

This did not happen when Dumbledore gave Harry a piercing look; I guess he was just looking sharply at Harry.

Remember, Dumbledore was extremely smart and had a lot of information that Harry didn't. Chances are that he could guess anything he was a bit uncertain about simply by observing Harry closely and his reactions to what Dumbledore was saying.

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my opionion is if albus dumbledore as head master made it forbidden to use veritaserum (truth potion) Order of the phoenix then why would he allow the use of legilimency? of course only when it was really needed half blood prince. He trusted harry well enough with all his secrets and more importatnly once said that truth is a good and terrible thing, he also said that curiosity should be treated with caution and I believe he wouldn't break his own values.

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