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In act 3, scene 2 of Shakespeare's Hamlet, the "play-within-a-play scene," Hamlet observes Claudius's reaction to the play and decides that the ghost of his father was telling the truth. Claudius murdered Hamlet's father.

Rosencrantz and Guildenstern come to Hamlet to tell him that Gertrude, Hamlet's mother, wishes to speak with him. Hamlet engages in some witty dialogue with them about a recorder, but they're interrupted by Polonius, who's also come to tell Hamlet that his mother wants to see him.

Hamlet has some nonsense dialogue with Polonius about the shape of clouds, then he sends everyone away.

HAMLET. ... 'tis now the very witching time of night,
When churchyards yawn, and hell itself breathes out
Contagion to this world. Now could I drink hot blood,
And do such bitter business as the day
Would quake to look on. (3.2.371-375)

Hamlet is on his way to his mother's rooms when he encounters Claudius on his knees, seemingly deep in prayer. Hamlet has just remarked how he could drink hot blood and that he's prepared to do whatever is necessary to avenge his father's murder.

HAMLET. Now might I do it pat, now he is praying;
And now I'll do't. (3.3.75-76)

We can imagine Hamlet quickly raising his sword over Claudius's head to bring it down through Claudius's body,or taking a preparatory backswing before plunging the blade into Claudius's back or cutting off his head.

Than Hamlet suddenly stops moving, frozen in time.

HAMLET. And so he goes to heaven... (3.3.76)

In that split second, is it possible that Hamlet suddenly realizes what he's preparing to do and realizes the consequences of his actions? But Hamlet doesn't say anything about realizing that he's about to kill a man. He spends the next twelve lines talking himself out of killing Claudius, and the following eight lines justifying his decision to himself.

Hamlet's stated reason for not wanting to kill Claudius is that he would be sending Claudius to heaven with his sins forgiven, rather than condemning Claudius's soul to hell for killing his father.

The real reason why Hamlet doesn't kill Claudius now—or at any other time in the play except in the last scene—is due to Hamlet's dual tragic flaws of indecision and inaction.

Throughout the play, Hamlet doesn't initiate any action. Hamlet only reacts to the circumstances in which he finds himself. At this moment, even with Claudius kneeling in front of him unaware and unprotected, there is nothing and no one prompting Hamlet to kill Claudius. So Hamlet does nothing, then he rationalizes his inaction to himself. Indecision and inaction are part of Hamlet's nature, part of his character, and ultimately lead to his tragic death.

What's remarkable is that at the end of this short soliloquy, after Hamlet decides to wait for a better time to kill Claudius, he simply dismisses the matter from his mind!

HAMLET. ...And that his soul may be as damn'd and black
As hell, whereto it goes. My mother stays.
This physic but prolongs thy sickly days. (3.3.96-98)

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There are several reasons as to why Prince Hamlet hesitates to kill King Claudius throughout the play. Initially, Hamlet is unsure that Claudius is responsible for his father's assassination. He even questions his father's ghost and wonders if the spirit has been sent from the devil. Hamlet also attempts to confirm Claudius's participation in his father's murder by reenacting King Hamlet's murder on stage in order to analyze Claudius's reaction. Being that Hamlet is a Christian prince, he is also concerned about his own soul and fears that he will be damned for eternity if he unjustly assassinates his uncle.

When Hamlet has the perfect opportunity to murder Claudius in act 3, scene 3, he unsheathes his sword only to contemplate his decision further. Hamlet says,

"Now might I do it pat. Now he is a-praying. And now I’ll do ’t. And so he goes to heaven. And so am I revenged.—That would be scanned. A villain kills my father, and, for that, I, his sole son, do this same villain send To heaven. Oh, this is hire and salary, not revenge." (3.3.74-80)

Hamlet once again reveals his religious mindstate by mentioning that he would be doing Claudius a favor by murdering him while he is praying. Hamlet believes that Claudius will go to heaven if he kills Claudius while he is confessing his sins.

While one could speculate that Hamlet also does not want to be accused of attempting to usurp power or to have Claudius's supporters attempt to harm him for assassinating the king, Hamlet's inability to act is most likely a combination of his moral and religious beliefs. He struggles to decide whether enacting revenge will doom his own soul or save King Claudius from eternal damnation.

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Hamlet hesitates to kill Claudius because he wants to be certain that Claudius is guilty.

Hamlet reenacts a murderous scene, searching for a visible sign of guilt from Claudius.

Hamlet cautiously searches for a definitive, visible sign of guilt.  He wants to be absolutely certain of Claudius' guilt.

This is a tragic flaw for Hamlet.  His insistence upon finding visible guilt from Claudius delays his action of killing Claudius, thus delaying the avenging of his father's death.

Hamlet's procrastination is well reasoned in that he desires to know the truth in reference to his father's murderer.

Nonetheless, Hamlet's procrastination allows Claudius time to suspect Hamlet's actions of avenging his father's death.

Claudius has Hamlet banished in a plot to have Hamlet killed.

Although Hamlet's hesitation to kill Claudius is an honorable quality, it is a tragic flaw that costs Hamlet his life, ultimately.

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Why does Hamlet hesitate over whether or not he should kill the king, his uncle Claudius?

Hamlet, in Shakespeare's Hamlet, tells you himself why he hesitates to kill Claudius:

Now might I do it pat, now 'a is a-praying,

And now I'll do't--and so 'a goes to heaven,

And so am I revenged.  That would be scanned [looked at or thought about again].

A villain kills my father, and for that,

I, his sole son, do this same villain send

To heaven.

Why, this is hire and salary, not revenge.  (Act 3.4.73-79)

Hamlet's Catholic beliefs suggest that if Claudius dies just after he's confessed, he will be forgiven of all of his sins and he will go to heaven.  Hamlet doesn't want to send Claudius to heaven. 

Hamlet's father, in the form of the Ghost, is lingering in a purgatory-like state, and Hamlet, if he were to kill a king, may go straight to hell.  Thus, Hamlet reasons, Claudius, the evil one of the three, will be the only one of the three to be rewarded with eternal salvation if he kills Claudius while he is confessing. 

Ironically, Claudius, while he is praying, is not really confessing.  He is unwilling to give up the benefits of his sin, and therefore does not confess or repent.  Hamlet could have killed Claudius while Claudius was praying, and order would have been restored in Denmark, presumably.

This makes Hamlet's decision to walk away and to not kill Claudius the climax of the play.  Hamlet is guilty of hubris, attempting to rise above his station in life.  Salvation is God's business, not Hamlet's.  Hamlet is playing God when he attempts to determine another human's eternal salvation.  The terrible loss of so many lives after Hamlet decides not to kill Claudius could have been avoided. 

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Why does Hamlet hesitate over whether or not he should kill the king, his uncle Claudius?

To add to the previous post, Hamlet delays for other reasons as well:

1.  He is a very moral individual.  He must make doubly sure that Claudius is actually guilty.  The act he is considering is regicide and to some extent patricide.  Hamlet knows the gravity of this action.  Killing a king and a stepfather is not something to be done without thought.  This type of consideration sets him apart from Laertes who is quite rash and foolhardy in his attempts to avenge his father's murder.

2.  Claudius is very powerful, and very smart.  Hamlet knows he will have only one chance to kill the king.  If he should fail, the consequences will be severe.  When Hamlet does take action, he makes a dreadful mistake--klling Polonius instead of Claudius.  From that point on, Hamlet is on the defense and has no opportunity until Act 5 to exact his revenge.  Hamlet's caution sets him apart from Fortinbras who is easily foiled in his attempts to avenge his father's death by his uncle and Claudius. 

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Why does Hamlet hesitate over whether or not he should kill the king, his uncle Claudius?

Several things probably keep Hamlet from "doing the deed."

1.  What Hamlet says is he doesn't want Claudius, the murderer of his father, to have more preparation for death than Claudius allowed King Hamlet.  The Ghost reveals to Hamlet that he died with his sins unconfessed; Hamlet is reluctant to kill Claudius as he is confessing. That would not be the purest form of revenge. The irony is, of course, that Claudius is not actually confessing his sins, so it might have been a perfect time for action.

2.  Hamlet also says he would rather "catch" him doing something else when he chooses to take his revenge.  He knows Claudius is a man of the flesh, and if he catches him in some frivolous or lustful pursuit Claudius will most certainly meet his demise in a sinful condition.

There are several other, more human nature kinds of considerations which may have prompted Hamlet to hold back his hand of revenge when presented with the opportunity.

3.  Hamlet is reluctant throughout the play and has demonstrated his ability to be--at least to some degree--a man of no action.  He is all hyped up for revenge, yet he has to check and re-check and ask a friend (Horatio) to bolster his certainty that the words of the Ghost were not a lie.

4.  Hamlet is not God, and taking a life is a mortal sin according to his religion.  Eternal personal damnation would, I think, give one pause.

5.  Hamlet is as certain as one can be by the time he sees Claudius alone with this opportunity in front of him, yet he has to be wondering how he would live with himself if he killed his uncle and then found out he was wrong.

6.  Revenge is always sweeter, they say, when the person who has done the wrong knows he's being repaid for his crime.  That might have happened in this particular scenario, though it's not likely unless Hamlet told on himself.  The more public end to Claudius, though unplanned, is much more gratifying, for then all knew of his perfidy and crime.

Hamlet could but does not exact his revenge at this moment in the play; this choice determines nearly everyone else's fate, including his own.

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How does Hamlet's "To be or not to be" speech reveal his hesitation to kill Claudius?

Hamlet does not directly discuss killing Claudius in this soliloquy, which is more of a meditation on life and death in general. Hamlet reveals himself to be disillusioned with life, to the point that, if we could know about the hereafter with more certainty, death might even be preferable:

To die, to sleep— 
No more—and by a sleep to say we end 
The heartache, and the thousand natural shocks 
That flesh is heir to. 'tis a consummation
Devoutly to be wish'd. To die, to sleep— 
To sleep—perchance to dream. Ay, there's the rub!

So this soliloquy, while very famous, is, at least on the surface, irrelevant to his desire to avenge his father's death. Yet, as we see throughout the first three acts, Hamlet's reflective and sensitive nature slows him in his pursuit of revenge. He is not a man of action, but rather given to moments, like the one in this soliloquy, of pondering many of the fundamental dilemmas of the human condition, all of which seem to be playing out in front of his very eyes. Shakespeare offers his audience a trade. We are not gratified by seeing Claudius get his just deserts until the end of the play, and then only at the cost of Hamlet's own life. But by delaying vengeance, Shakespeare creates one of the most complex and fascinating characters in the history of English literature, and this soliloquy is a crucial moment in this process. It is a window into a tortured, sensitive, and brilliant mind.

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