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A Midsummer Night's Dream

by William Shakespeare

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Why does Hippolyta initially seem hesitant to watch the play in act 5?

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In Act V, Hippolyta is initially hesitant to watch the play because she does not want the amateur actors to be put in a difficult position. 

I love not to see wretchedness o'er charged
And duty in his service perishing.
Essentially, Hippolyta feels that it is unkind to ask more of the actors than what they can deliver in terms of acting ability. She refers to Philostrate's previous words about the incompetence of the actors and their inability to execute good performances. Philostrate especially stresses the inability of the actors to do justice to a play named Pyramus and Thisbe. He tells Theseus that "in all the play/ there is not one word apt, one player fitted." What he means is that none of the actors can do justice to their roles in the play. In fact, Philostrate maintains that the actor playing Pyramus did such a terrible job that he (Philostrate) cried tears of laughter during the suicide scene. 
Unfortunately, Philostrate's words do not deter Theseus at all. In fact, he is adamant that Pyramus and Thisbe is just the sort of play he wants to see. When Hippolyta protests Theseus' decision, Theseus tells her that they should appreciate the intent of the actors rather than merely dwell upon their failures. Theseus invokes the responsibility of those who are superior to practice noblesse oblige (the duty of the privileged to deal benevolently or kindly with those who are less privileged).
The kinder we, to give them thanks for nothing.
Our sport shall be to take what they mistake.
And what poor duty cannot do, noble respect
Takes it in might, not merit.
Theseus reminds Hippolyta of the time some scholars approached him to give him a welcome. He remembers the nervousness of the scholars and how they flubbed the lines they so carefully memorized:
Where I have seen them shiver and look pale,
Make periods in the midst of sentences,
Throttle their practiced accent in their fears
Yet, Theseus assures Hippolyta that he greatly appreciated the sentiment behind the scholars' clumsy words. He advises Hippolyta to relate to the amateur actors the same way. Theseus' words apparently have an effect on Hippolyta, and they commence watching the play.
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Having heard of the total ineptness of the players (Peter Quince and his troupe), she fears they will be so bad that people will laugh at them. She doesn't think this is appropriate or compassionate.

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Hippolyta initially does not want to watch the play because Philostrate has told them that the play is especially horrible, but Philostrate also admits that it was so bad that he could not help but laugh.

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