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People don't like hypocrites, and they get a pretty bad rap in the Bible (especially from Jesus), but is hypocrisy itself a sin?

In reformed theology at least, every one is fallen and cannot avoid sin, and is by definition a hypocrite if they point out anyone else's sin. It seems to me that hypocrisy is a necessary evil in the process of accountability.

The difference I see is in the manner of being hypocritical, Jesus was critical of the prideful hypocrites who could not see the flaws in themselves, but maybe there is a safe way to be both hypocritical and humbly acknowledging your own sin?

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You are mistaken about your definition. Hypocrisy is pretending to be virtuous when you are not. It is not necessarily hypocritical to point out someone else's sin - only if you do so while pretending not to be sinful yourself. (There may be other reasons for not pointing out the sins of others apart from hypocrisy). –  DJClayworth Jul 22 '13 at 21:08
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Eh? Actually, the Bible is very clear about requiring believers to point out sin in one anothers' lives. Can I ask what source you're using for that definition of "hypocrisy?" Here are a few others that might be helpful: 1, 2, 3,4, 5. –  Philip Schaff Jul 22 '13 at 21:54
    
@PhilipSchaff What about John 8:7? –  Zetta Suro Aug 2 '13 at 18:54
    
@ZettaSuro: If you have questions about how to reconcile verses that command rebuke with those which require humility, that might be something to ask on the main board. I think that would be better than talking about it in comments. Thanks. –  Philip Schaff Aug 3 '13 at 7:51

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I'm going to take a stab at this:

Essentially, reformed theology suggests that man is completely sinful. That's the T in TULIP for Total Depravity. We're so sinful that we're beyond saving on our power.

The thing that might get lost in this is that even a single sin. No matter how small is enough to keep us completely separated from God.

Hypocrisy is definitely a sin. It's a sin motivated by pride, but ultimately it's bearing false witness. It's lying to yourself and other about how bad off your spiritual state really is.

Reformed theology though brings us out of that hypocrisy, we see and confess our sin for what it really is: Total and complete depravity and in such complete separation from God.

This is where we get to the good stuff though. We don't leave it there. As sinful, hypocritical and depraved as we are, God's grace is more than sufficient to cover it all. Yes hypocrisy is sin, and considering the nature of the reformers as intellectuals it was certainly one they struggled with (I certainly do myself), but the truth is that Grace is sufficient. We're forgiven.

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One sometimes hears the word "hypocrite" used to mean someone who preaches moral standards to which he himself does not conform. This behavior would be sinful if the person falsely claimed or pretended to be living up to those standards, but in the absence of such a claim or pretense there would not seem to be a sin in this preaching. Indeed, some people (for example parents and pastors) have the duty of teaching high standards of morality even if they themselves have failed to live up to those standards.

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